Greatest Chicago Sports Moments with Will Miles

positive thoughts and not even constructive criticism anymore, just love. Um, I'm gonna bring our guest on because I do want to talk to him about this, because he also has a wife who also does comedy and does projects with ladies and gentlemen. We are very very happy to have on an old friend. He's a writer for south Side, has his own special power. Um. You will probably know him from Two Black Dudes and Open Mic. Yeah, the kid, what's up? Well? How you doing? Man? Good? Good good?

I see where I see Megan and the pacers. Nice job. As as a virtual fan, by the way, thank you so much. Oh wow, Yeah, I gotta tell here. Well, let's talk to you and then I'll tell about my little virtual fan experience because it only ended like thirty minutes ago. Yeah, still writing that high Will is in his backyard and his beautiful home where I'm guessing your daughter. Your daughter is snapping. Yeah, she's napping in the side, so I'm not here. You're a new father. You're a

new father. Got a three weeks, four weeks, just hit the months the mark. Yeah, yeah, how does it feel? It feels good. It's uh, it's like it's still weird because it's like, oh, I'm you think every second you're like, I'm just me, regular me, and oh shoot, I'm a dad who isn't Well, you're still you, but yeah, you have that tact on responsibility. But you're going to be a father through the lens of Will Miles exactly. That's

so weird to think about. It's like, oh, yeah, I knew I was gonna be always be like a father, but I was always You never expect that you're going to be like, you know who you are and a father at the same time. You imagine there'll be some sort of like freaky Friday situation and then you'll just be carrying the baby in a three piece suit and know how to do everything, and it's like, oh, nope,

just Scott weed in the baby's hair. Um, we came over to socially distant meet your daughter in your backyard, and you were holding her so confidently, and c J goes, how's he holding her like a football? Which is like I was. So sometimes you see Dad's and it's like, oh boy, there this they're holding it like the damn sack of flower. But you had Stella you were doing moves with Are you at all let it down? I

had some practice. My nieces are eleven pretty soon. So when I would like sort of sneak sneak to New York and be like gone for so long because I knew I could stay there if I babysat my brother and his wife. So I was like, all right, well here's the good reason to go to New York repeatedly, and so I just I had to be good at it in order to like sleep there and do comedy at night. So I was like, let me figure this out.

That is a good trade off, because those are skills that you picked up in that you're now using for your own children, your own child wild Now, does does Stilla have sporty gear? Does she have bull stuff? She has? Uh? Does she have bull stuff? I think I know she has basketball items. I believe you guys got us some as well, And I think I got you like that. I think I got you like practical stuff. Yeah, yeah, I feel like there was one like you guys got

practical and there was one or two. Okay, yeah, he'll slip, he'll slip in. So Kyrie spongebobs for kids, and I'm like, where did this come from? My brother actually got my niece some uh some what was it? Like some Tiger Kyrie's. They were for children and we were so excited to have her open those up and she didn't care at all. Yeah, I already I am looking at like goat baby sneakers. Oh my gosh. Yeah, So how how are you going

about that? Are you just gonna, you know, dress her up and all all the type of gear, the fashion that you like and then see how she likes it. Yeah, I'm hoping to influence her in some way with how she dresses, trying to raise a little lean away. But well, you and Julie are pretty fashionable. I think it'll just rub off naturally, I hope. So yeah, yeah that'd be great, thank you. Yeah, but she gets pick her own style

whenever she wants, absolutely absolutely. Yeah. Uh So Chicago basketball, I feel like the topic for anyone who didn't read the title is greatest Chicago sports Moments. Oh, there may be people that read the title and said, no, I don't want to be in this circulture of them just talking about Chicago. Yeah, because it's if you are not in the comedy community, you may not know how annoying people from Chicago come across. Um, and I'm c J

and are not from Chicago. We are comedically considered from Chicago, and people hate us. Like the group of us. We're loud, we're annoying, we show up late, we are funnier than most people, and we have bad attitudes and we definitely take over a room. Um. So sometimes you know, they'll be some of us roll in and you'll see eyes roll and they're right. Those people are right. If I was not part of the Chicago comedy scene, I would

also hate our crew. Yeah. So it's like, you guys are correct, we are annoying, But Chicago sports fans that is a whole another level of obnoxious. Well, I just think to the comedy thing. It is. It's hard because we all came up around the same time and all started doing well around the same time, so we were all like we went from all being an open mics being friends, which everybody an open mics was friends is

super annoying. But then when you carried it over to like, oh no, now we're all in Montreal, or we're all now we're all on this Comedy Central set, it's like, well, we're still the same annoying open micers. We just all have now done things. We're scared and nervous, and we were gonna, you know, latch onto our friends we started out with, Yeah, exactly, it just so happens they're still around. It's great now. Oh sorry, you you love Chicago though,

you love where you're from. Some people don't love where they're from. But you really represent Chicago. Yeah, I love it. And you are from boys Town. I mean when you were growing up, would you guys say lake View or Boys Town? We would say, you know, I think lake View, because I don't know how many people said boys don't. I always thought it maybe was like a mean thing to say. It was like, oh, man, Boystown, you can't call me from like Boystown. Yeah, but you were a

boy and you were from that town exactly. Yeah, So boys Town in Chicago is sort of like the gay neighborhood, tons of gay bars, that's where Pride, the everything goes through there. Very very fun. It's in the overall Lakeview neighborhood, which then like butts up exactly next to Wrigley Field. So it's the northeast corridor of Chicago where Will is from. And Andy, I mean, yeah, Born raised. It's you're You're actually probably when of the least annoying Chicago sports fans

I've ever encountered. Though it's got to be Cubs fans, especially to super annoying people in general. Now do you do you get like a chip on your shoulder because

you're from like right by the state? Um? Yeah, yeah, I mean I love the Cubs, but also I I understand the full hatred for their fan base because I mean, like we were even saying because we're trying to, you know, figure out volume levels for raising our kids child and uh and I'm like, well, I grew up near Wrigley Fields, so I don't know what that's like because people were drunk screaming my entire life outside of my croom window. So I have no like context for like, oh it

should be quiet for a baby. It's like, well, I never was quiet for me, So I have no idea, and I'm like, maybe it's good to get used to like drunk assholes leaving some of the first night games

ever in field. I really do think that's part of why we, you know, have pounces success in comedy is that most of the shows we were doing, we're just bars that had just got done watching a Cubs Bowls, Blackhawks Bears game and now surprise, a comedy show with a bunch of people who have just started and we were trying to vince them and yell over them and they're all wasted. Yeah. But yeah, I I love the clubs,

but yeah, again, hatred of the fans. And the thing I noticed growing up was how many fans were not from Chicago. Like it's a lot of Illinois at all. Yeah, they're moving from Iowa or like you know, not probably Indiana because they've got their own No, No, there's tons of I mean, we don't have a baseball team, so it's kind of split between the Cubs and the Reds. Yeah, but it's way more I would say Indianapolis if you were like going around and asking people Cups fans, but

they have no knowledge of anything that's happening. They just want to get sucked up. Yeah, And I think the team was different, which will go into one of my sports things. But like the teams and the and the fans were different when I was a kid. I'm almost certain when I was an adult, when we were doing comedy, everybody was like pretty one note. I felt like, you know, like land and White most fans, and I don't remember them being that way growing up now. When Rookie of

the Year came out, was that. I mean, I can't even imagine a movie being about me as a child. Yeah, what was that? Like? Huge? And I kind of remember when they were filming it because it was it's so big, and you know, that's the movie. We all everybody at school at least watched it and try to do the arm thing. We all thought we're gonna break our arms and sad was gonna be amazing for our career. It's

like a baseball player. But they also shot Babe down the Street from me too, Why in the City Babe, the one with John Goodman, the other Babe my bad. In my defense, the Babe Pig movie is much more famous than the Babe Babe Ruth movie. Yes, wait, Why did they shoot it in your hometown? He didn't play in Chicago? Are you playing? I know? I never under really is the shittiest looking stadium. I mean, I mean, the most historical looking stadium, and so they it looks

like it's in the nineteenth century exactly. They didn't have to change much. But I just remember some somebody coming outside or like our neighbor was one of my friends from elementary school, was like, uh, you know, they're shooting babe down the street. The dad from Rosanna's Houseide, the dad from Roseanne has a name, and it's that's what you said. Um were you? Was there ever a point that you were like, the White Sox are cool? Though? Nah? I mean oh five, yeah, as an adult, but never

as a kid. As a kid, it was always like, I can't even understand how you could like the White Sox. That's so funny. I don't know that's ingrained in US so early. The sports team ship where you're like, oh, I guess I hate the other team well and then yeah. I mean. The thing is like in the nineties, I didn't think there was any other basketball teams besides the Bowls.

You know, I didn't even live I lived in Iowa for when I was born in eighties seven, and Iowa lived there for five years, but it was just WJ and so that was the only team that was being played. Yeah, but what was it like? That's what this is why I always ask our friends who grew up in Chicago, what was it like being a Bowls fan in the nineties as a kid? Amazing in the eighties, well, because like late eighties is when we started to get good.

The nineties when we were the best, And it is truly, you don't know how amazing your squad is until you realize that other people didn't grow up like that. Like I had family in New York and they were Knicks fans, and I'd be like, oh my god, you must be so miserable. We'd beat you every time. This must suck. Your life must be terrible as a result of us constantly just sucking you over and winning championships. Yeah, I don't know, sorry the other fans, No, Megan. Megan went silent. Yeah,

I know, I know. Well, you know, I'm just trying to practice something in my own life where when men are speaking, I like to I like to just you know, get a little quiet and listen to them, and maybe I can learn and maybe I can grow from from the smart men around people and listening to you ears open, eyes, open, heart open, let all of the masculine bulls dick sucking flow into and were fun to watch. Thank you, thank you.

Know it's it's fine. I honestly like, as a kid who you grow up with your team not winning all the time, you start to understand adversity and like I played sports growing up and I would lose, and then I'd be like, oh, okay, Reggie's lost to you know, like you do you kind of like learn how that Once I didn't get a dollhouse. My mom got caned by a con man and um, it's a long story. And I was supposed I was supposed to get a dollhouse for like my it was like Christmas my when

I was four, and it didn't come. And my aunt was like, well, it's time she starts learning about disappointment in life. Um, and like that's harsh, but it's true. Like growing up watching teams that lose and it's not like these were terrible teams, but you do start to be like, oh, yeah, I'm not gonna win all the time, everything isn't gonna go my way. Um, but like that, I mean, I'm telling you that as a white woman from Indiana to a black man from Chicago, You're like,

you just let my team win. I've got enough ship going wrong for me. Okay, but yeah, no, the teams were all like it must be such a different lesson back then because the teams were so good. I mean, I guess the teams are really good now we're watching the weird version of it. But they were. Everybody was like championship level back then, like the best player ever.

When you see and not so much now, but like a few years ago, when you would see kids at Warriors games, it'd be like, fuck you kid, you don't deserve it. You don't deserve first of all, you're rich. Second of all, your parents suck, and you don't deserve to get to be in this building just watching this dominant team. You haven't earned it. But but if I saw a little you at a Bulls game, I don't think I would think you suck, I know, but probably because it was just a bunch of like winners gloating

over and over again. That's I wonder if there is like a if there's a correlation with a lot of famous comedians are out of Chicago, especially in the eighties and nineties, like and then obviously our group that we talked about. Do you think any of it there's a correlation to winning sports teams. Yeah, we we tasted winning

early on, especially Chicago Stadium Bulls. That was the first few change when we had access to the stadium that a lot of like everybody lost access after when it moved to the United Center because it just it seemed like a much richer place and it was like a lot of uh, we were really big by then, so everybody wanted to come to a Bulls gamp those first three three championship seasons when you could still get tickets to a game, it was pretty incredible because it was

like everybody in the whole city was seeing just winners. So no matter where you were, you're like, I guess I could win. Winning creates like delusion kind of and delusion is something that's actually quite important in what we do. But you have to have kind of like the right amount. If you have too much, oh boy, and if you have not enough, you know, so like there is a sweet spot of of delusion and I'm happy that you,

growing up as a winner, did not like overshoot your delusion. Yeah, and you saw like the wind the people who were they even overshot it or undershot it, and it's like, yeah, you're gonna peak in high school probably those kind of people. Yeah, you gotta believe. And your delusion is such an important thing to think, like, I'm gonna make it at all, so stupid if you really think about it. But then

you're like what you do now? When we we decided or you just we we wanted to pick a topic that was gonna be not labor intensive research wise, for for you specifically because you have a baby and we love you and we wanted you to do the podcast so badly that we kind of, you know, give you a little softball. Um. But it was. But it also made me think of a topic that I'd like to do in the future, which is greatest sports city because people have real strong opinions when it comes to the Boston's,

the Phillies, the New York's, the Chicago's. Of course l A wants to be in there. I'm sure places in Texas think they deserve to be in there. I feel like I'm I'm from a great d C. Yeah, there's lots of um. But since we have you, I'm putting you on the spot with this. Do you feel like Chicago is the greatest sports city? Uh? I mean I want to say yes, just because I in my lifetime I've seen every team win a championship, which feels good.

That's pretty amazing. Since so I do think, yeah, in the past thirty seven years, we've been the hell of a sport city on everything. Well, and like we we've all lived in New York and now in Los Angeles in addition to Chicago, and you kind of see how the city reacts differently, like and I know, of course New York in l A has lots of transplants, so when the Dodgers are in, it's not gonna like be.

But even in even in Chicago, when there's not Chicago teams in the in the Finals, or in the super Bowl or in the World Series, the city shuts down like we would not have shows may be like oh, Wednesdays in in jail in June k is gonna be canceled because they'll be the Finals happening, and and out here it's like the Rams were in the super Bowl and it was business as usual, like totally normal out here.

I said that to a lift driver as it was happening, because I think I flew back from somewhere the day that the rams were like around the time it was like super Bowls next week, and I was like, man, who's in the super Bowl this year? And he was like, we are, And I was like, really, like the ship, I don't see anything nothing. I was like, damn, I'm not paying attention, I guess, and neither of the whole city. No, I don't know. I mean like, yeah, they left, they

came back. You know. I think if you got into like the muddiness of I mean teams, it would be wild to me if a professional team left Chicago, ever, that would be like like that would be the last chapter of Sure, yeah that would make sense. Oh the Bowls are leaving. Okay, yeah that makes sense. Like before we get to the topic, I do want to ask you this, because this is the one bright thing of the last few months. Was the last dance? How did

you feel about the last dance? What was your favorite part? Uh? Favorite parts were just kind of everything. But I loved how because michaels or in such an asshole. Yeah, and it was like you could kind of see it, but also you got to see him explain why he was an asshole. So that was hope for me to watch, like, oh man, good, you are a dick. You will admit it, and you had like lied to make things happen, but

it's like, I guess it worked. I don't. Yeah, it was just kind of fun seeing him be aware of that because we were it was always like speculation that he was an asshole and you're like, oh, no, he needed to be an asshole to be the best, and he was. Um, did Julia your wife watch the last dance as well? Yeah? She was right there, and what

was what was her reaction like to it? She obviously didn't care as much, but she was watching me be so excited that she was like huh, that's weird because like every and and it was the thing that I'm sure every Chicago like uh, wife of somebody from Chicago, husband and somebody from Chicago experience where it's like I was there or like I remember that day like yeah, because I yeah, there are so many experiences in there where I was like, oh yeah, I forgot like I

was there for a lot of the Chicago stadium stuff. That's crazy. I mean yeah, even for you, Megan, it was like when we got to the Pacers stuff, you were like, oh, I remember that day, and you know, watching it on this Would Square arena, I was like, oh, I miss you. Yeah, loud, dirty giant piece of crap. I miss you so much. It was great wondering if I might have gone to Market Square even back then, three hours down to see a little road Bulls game. That sounds fun as hell. Yeah, go eat at I

don't know. We probably had a chance downtown or something that. Yeah, I was gonna say cheesecake factory. We didn't have cheesecake factory back then. Is that new? I don't know, but I would love to know where the original one is. That seems like a trip you and I will take. I'm sure, yeah, I think so, yeah, because I think the owner is from Mountain Here. Um, okay, so let's take a quick break and then we'll be back with

our picks. And we're back, and as a reminder, we are doing greatest Chicago sports moments with our guest here, Will Miles. Will, why don't you kick us off with your your third pick? We'll go three to third Pig in Chicago sports history is a well, actually all of them might be personal. Number three is when I saw Andre Dawson and On Dunstan in my barbershop. Whoa ho ship,

Yeah you we talked about this. This is I like I thought when you said weirdly specific, I thought you meant like games you were, well, stay on the same time you're in and by your barbershop. You don't work there. It's just weird, Okay, it's the one I go to. It's the one I went to Terrell's barbershop, which was at the Sheridan Red Line stop from Wrigley. Uh. And I just remember one day, like my brother had been going there for years because he's six years older, so

it was his barbershop first. And then I was like all right, I think I started going at like three or four years old, every black kid, and and then uh yeah, I just walked in one day and like Andre Dustin was in Terrell's chair, and I think Sean was like waiting or like my dad and I used to always call him schiwan because that's how it's spelled, but like he was way and I was just remember being like, what the fuck? These are like absolute heroes.

They were two of the biggest like ever at the time. I couldn't They were their biggest players I ever saw at the time. Ever, I was like, these are these are clearly like the basketball icons you know before Sammy Sosa and everything. Did their hair look good? Well? The thing was Andre Dawson had a Jerry curl and I didn't understand why he was even there. I think you

must have just been getting a pine up. But he was in the chair for like an hour, just talking Dawn and I got his autograph and I got Sewan Dunceon's autograph. That's what I was wondering. How do you approach them? Right? Or? Were you like, yeah, is that a question you have when you're six, whether or not

you should approach them? Yeah? Definitely. Well, I was like, I don't know how to, like, I've only seen this guy on TV, and I've only seen this guy on TV, Like, how do I even come up and say, hello, you're a baseball player by yourself? I think my mom was there, okay,

but she didn't. She didn't know who they were. She didn't really like only after I think I was with my brother, and maybe we both got like really excited about them, and so she must have been like, well, that must be somebody, and they're in perfect shapes, so she was like, Wow, my son's really love hot men. It's interesting. They were always here and there's just kind of flabby men, but now there's these jacked men and they want autographs and photos. Interesting. That's gotta be awesome. Yeah.

I mean, I can't imagine if I grew up in the city, the same city as some of my favorite athletes, it would be like, Hey, we're getting on our bikes and we're gonna go find their house. Yeah. Yeah. So the fact that you were like polite, like should I like you guys in a in a barbershop? I would have been like, what's up? Man? Can I play on the Cubs? Like that's the kind of kid that I was.

Maybe you guys rookie of the Year. Maybe it's for the best that you grew up in a town without any major sports teams, Like that's actually what you needed to do. Um, okay, well that's a great pick. All right, thanks? Really really personal. I don't mean the thing is I'm having a little fun. Can I have a little fun? Okay, do you want to want me to go, I'll go. Sorry, that was me to just see um my my number three pick. It happened today. They fired Jim Boylan. This

is a huge sports sports news, Sports news. Jim Boylan maybe the worst coach in sports history. And we've had. Yeah, there's been some stinkers since Phil Jackson and before Phil Jackson, I think, you know, and they gotta they got a new GM and they were gonna I believe they were like, no, we have no plans on firing Jim Boylan and that team. I mean, Megan name one personal bowls. Um I must said Marco Rubio. Somebody there's someone like lu all day,

there's everybody's there's no one killed. You know what. That brings up a great time when you also made a shitty pick, you said coach Tip and I was one of the greatest coaches of all and he just said he killed DA but he gave us some great moments. No, he was. He was one of the best coaches. I said, listen, listen. Clark was on the episode and Clark goes, no, just s Clark, And it's like people still bring it up

to me. They're like, is your husband. Okay, like are you It seems it seems like you love him, but I don't know if he's mentally fully there is this some sort of like make a wish thing that you guys are doing. Okay, so when that was going on, but yeah, when you realize how much you've ruined those players lives, yeah, maybe it wasn't me, but I don't

know his job. So Jim Boylan is fired. Heired. You're happier today than of the three championships you picks because there were there's like a lot of them and you've run out. Now you only have two picks left. Al Right, Okay, I'm happy for I guess we'll move on to me, the only person taking this seriously. Um. And the thing is I had like a silly one and I was like, no, I'll put it in honorable mention, am professional? Okay? No, So my number three is this was my number one.

I moved it back to my number three and it is the black Hawks winning three Stanley Cup championships in five years. That is like, if that happens in a city, you can make the case to be like, no, you get nothing else. Now you know you've had you've eaten enough, no more. Um I was there. We were all there in for that one. I was still there and then I was gone. But they were. I mean, everyone says playoff hockey is the best there, it's the it's the

absolute most like cutthroat, exciting fun. We're obviously seeing some of that even now these NHL games. Great job on their bubble too. And yeah, the black Hawks, they were like a really fun team, and we knew comedians that were friends with them, and so you would sort of

like field tangentially close. I definitely like met one or two of them and you're like, oh my god, Like they were just really cool and the city the parade was so fun for them, Like it was kind of like everybody wants the Bulls to win, everybody wants the Bears to win, and then this the city is split, and it almost feels like the black Hawks are sort of like the kid brother that everybody loves the most. But sometimes it does get a little like lost in

the shuffle of all the things going on. But when they do succeed, it's like, oh my god, we all love them. They're the best, and their games are so fun, and yeah, I just think for any organization to be able to win three championships in five years is extremely impressive. It was like a dynasty, and they were one of only two dynasties we've really had. I mean they tried

to call embarrassing in dynasty, but really just championships. But yeah, like seeing that was amazing because every the black Hawks before that were just a fashion thing. Like I'm from Chicago. The logo is cool, even though it's mildly rapeist, but it's like it's cool and I'm gonna wear it regularly. And the you know, it doesn't have any gang affiliations really, so that was why it was popular. And then when they won, you're like, well, yeah, of course I knew

the whole time. Yeah, I mean I own a Blackhawks Christmas vacation griswald Um sweater that he wore on our honeymoon um because that's how c J shows his love uh sports teams off for you and everything. Right, Yeah, he comes fan. Yeah, he's he's definitely he's like Suburbs, so North Suburbs. I'd say he's a Chevy Chase though, racist, racist, old man. I'm sure he's a Cubs fan. Demo still works we got you. Okay, we'll give us your second pick. Second pick, I'm gonna go with the Cubs winning the

World Series. Ye good job. Yeah that was and this is slightly personal, but it was I'd love to hear. Okay. So you were living in New York at the time. Yeah, I was living night and just take us through. Everybody knows, like it went to Game seven, so that that first

of all that week. I was in l A before that, and I was doing sets in l A. I had never really been to l A. So I was visiting and I was doing a bunch of sets, and uh, the Dodgers were playing the Cubs, and the last game of that series, I was out at a bar watching it and I cheered so loud when the Cubs wanted ran around the bar and I forgot where. I was like, hey,

you can't do that, and I was like right. So when I went back to New York, it was also one of the like big first things I got, I think was Comedy Central comics to watch, and I got it and that night was the night of comics to watch. Was I was there with you. Yeah, the last game of the World Series, and it was insane and so I did my I didn't watch anybody else that night.

I went in to do my set. Then I immediately went back out to watch the game in the lobby and then Caroline, and then the show ended, and everybody was like, I'm supposed to meet and greed and my manager was like, all right, great, we're meeting and greeting and I was like, sure, but I am still watching the game. I do care that all these people want to meet or whatever, but I don't at the same time,

and then it started raining. And then right as it ended and it started raining, everybody was like I was like ah, and then um, the venue changed. We all went to an after party down the street. And as we're walking in to the venue to the like second after party venue or whatever, the game starts back up. And so everybody has just seen me not pay attention to them at Caroline, so they're like, now they're rooting

for me to root for the Cubs. So like the whole after party is everybody being like, well, I mean, I guess we're into the Cubs now, because it was I mean, there's the World Series two. Everybody was into it, but they knew I was like dedicated. Next to the Ridley Field and everything. So then they won, and like I ran around the block and everybody was tugging me and cheering me, like like I won. And then I like FaceTime my mom and introduced to everybody at Comedy

Central and everything that like, look, mom, we won. This is everybody. I FaceTime my brother who was in Chicago at the time, and he was like running around in Wrigley like Wrigleyville because they shut the streets down everything, and he was out there with them, and so we were all. I was just facetiving family, FaceTime my dad. It was just nuts all the same night that I was like supposed to be really happy about this other thing, but I was even more happy about this, the Cubs winning.

So it's just a weird, weird day, but it sounds like a great day. You have a one and now you have a wonderful career. So all I just like love the image of like industry people being like what's going on. He's from Wrigleyville and the and it was a tiny TV like behind the bar, and like half of us were yet out there watching in the lobby and people in the show and it's just like there's a way. I mean, not to speak ill of any of the comics on it, but the game was more interesting.

Why were you at comics to watch? You just watching friends? Yeah? Oh, I remember why you were there with that? Wasn't Tommy there too? You guys were both there because I remember I needed the Chicago people around. Oh yeah, I know you're saying, sure about I know, I know, I but that. I thought Will was trying to cover for me. I was, But yeah, it wasn't Tommy there. Don't you bring sweet Tommy Mack into him down Tommy watching other comics? Of course? Great.

I mean I'm glad Will had to set a good set and that the Cubs one and then fuck everybody else, you know what, I know exactly all right? Remember two pick, I was gonna say the Bears, the Bears. I think the Bears SNL SKA. I think it's a cultural phenomenon.

It was, it was. It's the true like in my field of trying to figure out the overlap between pop culture and sports, the Bears is like the dream to say, you came up with Bears on SNL and we still see the Bears commercials to this day, And I think it might be the height of professional sports comedy out there. I don't know. Yeah, I mean, Dick has had a tough few weeks, So what happened? I don't think, I know. I don't think he's down with the movement, if you

know what I mean. Um, yeah, he's not. Someone did what I can't. An athlete told me his story once of golfing with him, and and it was it was Dick because course in some like I don't know if he owns the course or he's like part of a course. And Dick could just peed on the green, just like whipped out his dick and pete on the green. It didn't even didn't even go to the woods. Um, okay, so your pick is not the Bears team, but the Bears sketched the Bears sketch. I feel I feel like

I'm crazy. Is how it like? It did? It did really reach everybody? It's not even that funny. Yeah that's true, you know, it just is like, yeah, it's iconic. It's just like captured at a time in sports and pop culture. And yeah, again, the Bears haven't been good for a minute, and we're still seeing the Bears commercials on TV. Yeah, they've almost never really been that good. It's like, well, you know, pretty good the Rex. Yeah, but X was awful and he blew it. That's Megan's Megan lived in

Rex's apartment. Oh god, not with him. He didn't, he had vacated it. But he left a bunch of stuff. He left a knee braise. He left some like kind of body shirt. You know those shirts that have like different um like that when you roll the cuff up, it's like a different pattern. He left some of those. He left some shoes, like, he did leave some weird things behind. And Robbie Gold had been living there, and

I think he left something behind. Two umb Okay, So that brings me to my second pick, which is when the Bears won the Super Bowl. So the Bears the Super Bowl Shuffle, then they won the Super Bowl actually in eighty six. That the NFL like schedule confuses me all the time, just because it's like the Super Bowl is always in the next year, and I don't know why. My brain just like can't handle it. Um. So it's the eighty five Bears. My mom was pregnant with me at that time, and I was I was breeched so

like my feet were coming out, We're gonna come out first. Um. And I was Doe in like two weeks. And so she had done all this stuff to try and flip me back over and just like couldn't do it. Um. And she was pissed, of course, I mean or annoyed because you can you can't come out feet first. It's not water slide um. And so isn't think she had just sort of like, I don't know, maybe given up. And then she said during the Super Bowl I flipped

back over. Wow, what do you think that me? I think I always thought it meant like I was watching the game and I was like, I love this man. No, no, no, no. I think I was doing an audition for the Jesse White Tumblers in Utero. You know, I said, check that out, look at what I can do. Yeah, that was like you were inspired by Walter Payton or something. I don't know. But people, I mean people cling to those eighty five bears. I'm a huge PTI fan, and like will Bon brings

it up once a week. Um, it really and I you know, I understand that I do that with an and it's sort of it's tough too, because that was the last time. So I think that's why it's like so burned in everyone's memories, and Bears fans had that delusion that we were kind of talking about, where you know, it's not as bad as Brown's fans, but Bears fans are they. I think Chicago fans are the hardest on

the Bears. I really do, because they'll be like, we're gonna no, you know, squads looking good, squads looking good. And then after like one Mitch Robinsky funk up there, like get what it's like. Obviously he it was a bad pick, but it's not Mitch's fault, you know, like he wants to be good too. He would love to be as good as Patrick Mahomes. He's trying. But I remember when they gave Cutler that deal where they were like, we're hoping we'll pay him this huge amount of money

and he'll play up to it. It's like, that's not ever how anyone has done a contract. That's the dumbest thing I've ever heard. Um right, yeah, well, but they were just like he hadn't been that good and then they overpaid him, being like now he'll be good, And it's like you can't will someone into being better as a quarterback, and yeah, the quarterback position has always kind

of plagued them. And and I guess when I hear people complain about the Bears not having one one and now what is it years, it's like you guys have had so much that like this is this is actually the team that is going to have a drought. And that's and that's like what you guys do deserve. Damn. Sorry, you're right. We are the worst fans for Bears, though, I think that is a lot to do with it, because we will make like a we made Cutler cry,

basically made Eric Kramer cry, We made Rex cry. Kyle Orton was like, get me out of here, y'all all broken cement, Yeah, Matt Forte. We broke so many people who were like had the talent that all they needed was a bush and like they had any push it off from the fan base to be like, all right, that was just one bad thing, keep going. But we never gave anybody that sort of thing. It's like, oh, that was one bad thing. I hate you. Now here's

some memes about how lazy you are. Here's here's you eating a hot dog on the sideline, and it's like he's a diabetic. He needs a hot dog. Just let us have that. I mean, who's starting for the Bears this year? No, I don't know. I think they said it's gonna be um a competition. They have a new No, they don't have a new coach. They would have been a great hard knocks team. Yeah, because now we're getting

two teams. And I honestly think they picked it for production reasons, because like it's out here in l A and it's easier with COVID. But I do think the Bears would have been a really interesting team. They're so they're kind of like secretive and old school. You know, they've got no cheerleaders, they're they're one of the original and they just really seemed to like cling to that history and and the mc MCCASKI, oh no, I didn't know. No, I mean just in terms of they just haven't done

really well with having a team. Yeah, they're not like Dolan status yet, but they're like, you know, they they've been sucking up for that long and it's like, all right, well let's take a break and then we'll be back with our number one picks. All right, and we are back with our number one picks. Will if you're not familiar. This is what we do. Megan and I will choose first and you'll be our grand finale. Okay, cool, all right, Megan,

do you want to go? Yeah? So my honorable mention is um the Bears getting to lose to the Pulse in the songol I actually I think that is I hear. Let me frame it this way. The Bears making it to the Super Bowl, Lovey Smith Tony Dungee was the first time a black Head coach Um had made it to the Super Bowl. And then we had two facing each other. Devin Hester returns the kickoff for a touchdown and then and then you know, nothing went right after that,

and that's fine, that's what y'all deserve. M But it was you were worried. No, you know what it was. I was actually watching it in Chicago. We were at Mullins, which of the year as a Colts bar, but when the Bears are in the Super Bowl, it's a Bear's bar, which we did not know. And they were so I mean, the place like erupted and we were a table of maybe like eight Colts fans and you just have to be like, that's okay. So no, that's you know what, he was gonna get one. He was gonna get one.

And now it's out of the way and it's pouring rain and it's in Miami and what like, we it's just gonna be. It ended up being a showdown where Dominic Rhodes was actually the m v P, which is insane. But they gave it to Peyton of course, which I hope Peyton gave Dominic Rhodes his like Silverado. He won because he really truly deserved it. Um. But yeah, of course I was scared and then which led me to

over drinking. So I actually don't really remember the end of the game, but I was extremely happy, and I did get thrown out of the bar. But I do think it's really nice that the Bears got to lose to the Colts in the Super Bowl. Okay, so it felt good for you too, Uh well, we didn't deserve it that year. I mean really, defense was amazed. I love Peanut, but like, who's not an FBI agent? Yeah yeah, yeah, but I mean, yeah, you guys had it. It was one of those where it was like, yeah, of course

they're gonna win. I don't know, maybe that's just like a defeatist. Edit. I really felt like at the time, I was like, yeah, of course they're gonna win. We're not gonna We're not built for this. Really out thank you. You didn't even you didn't even know me yet, but

I appreciate it. That was it weird. That was actually the first time I was in Chicago, or no, not the first time, but it was I was visiting there to see if I was going to move there, so that I that's my only honorable mention I have, and then my number one. I guess it's a top. It was just going to be the Cubs winning the World Series, but you said that, And I also I feel so bad for the White Sox. They also won the World

Series in two thousand and five. Ozzy Gean famously told me that if I wanted to be famous in this country, I should kill a person. I mean, they're fun, that's a fun Remember he threw j Marriotti. He wasn't allowed to come into like the clubhouse, he couldn't be a press Conferenceszynski was crazy told me, was I mean, that was like a really really really fun team. And I

just feel like they get so overshadow owed. And and they also deserve, you know, their day in the sun, and and their fans are equally ravenous and definitely like much more of a chip on their shoulder because they feel like the second uh team, like the passenger team to the Cubs. But they won, and they won like before the Cubs won, and yeah, I just I loved that team. And I thought it was like kind of shitty how Chicago won a World Series and more than half of the city was like pooh pooing it and

acting like they didn't win a World Series. Oh really, I see if my roommate who you guys met, and no, I think even my old roommate Adam, he uh he's a White Sex fan because he's from the South six from right around there. So I was in my boy Steve. You also know, we were all watching that game and uh, that whole series. The whole year we were watching the White Sex So I I became a huge fan of

the White Sox that year. Pres seemed like a dude who might calmed the inn word, but I love time because when he fought that dude, that fight was so dope that I was like, you know what, I just don't want to know if he says the inn word, like that's where you're like, I just never asked him if he's ever said it, because I love that guy, right, Yeah, don't send per Zinski on Z show. And he swept to like it was like a definitive, like we are whooping your ass from the South side of Chicago. Yeah,

they're better fans. The Socks fans are better fans. I'll give them that. Damn all right, um My number one pick I'm gonna go with because I also don't want to take any from you, well just in case, but I'm gonna go with Jordan's. I'm back him coming back, coming back the Bowls. It's just again, you know, and it took the last dance for me to again put him back in the goat the true greatest of all time. And it's just the fact that you can win three eve and I don't I don't count lose them losing

in the playoffs in his first year coming back. You know, it's just like the dude's been playing a completely different sport, you know, thinking he was never gonna come back, and he's like, hey, I'll go back, and then yeah, and then winning three in a row. I don't think we'll ever see anything like that. And you know, I think with especially with Geordan, I know people are like Bill Russell was eleven, but like them winning six in the nineties and that era with the Malone's, the Ewings, the

Reggie Miller, like Barkley a came that was impressive. Six in that era is is insane to me. So and it all because Jordans came back and that was like one of the sports wise that was the biggest story of my life as a kid growing up. And I mean that the whole Lebron Jordan argument that I'm sure you got into the clark On here. It is like Lebron doesn't have what Jordan's has because that's why Jordan's a go. But it's for the best man. He doesn't.

He's such a better person. Yeah, he said, like I don't want him to have whatever it is that made Jordans be like I took that personally about everything that and made up ship too, like personally and they're like that never even happened, Like I don't want Lebron to be that guy. Lebron just bought out Dodger, say to him so we could vote. Yeah, it's like I'd rather that guy. No, but it's like yeah, people like no, but he did that, well, he didn't. He didn't win

the finals, you know, nine times in a row. That's all crazy sports fans. But all right. I do think that whoever wins, whatever team wins the championship this year, it's gonna be extremely extremely difficult. And if that ends up being Lebron, I really do think you have to give him an edge because he basically made this bubble happens like singlehandedly. It feels like in some ways he's down here. What does are you being chased by a bug?

Like I thought it was like I thought there was a ghost we couldn't see, you know, like this is how you go out. I think if Lebron is able to win the championship bubble on top of having a championship with the Calves and then two with the Heat too, then it's like he's got that's three different teams, but the third team is within this really insane situation that so few people could duell. I mean, and you see

him struggling he actually is. And you see people like t J. Warren Dame that are able to like elevate that you you definitely are like, oh, these circumstances are they're affecting people differently. Um, and I mean these playoffs are going to be so fun and I'm so happy we have it. But if he is able to pull this off, yeah I think he's then he's the go oh my god, my god, oh my god, Will Will right now? He will just ran down the stairs. This

will be careful. Don't like that bug. That bug is a Kobe fan And it's like, how dare you not in the conversation? Yeah? Sorry, man, he's in there too. We like, Kobe bug, are you okay? Are you okay? Yeah? I'm okay. Because our screen also froze for seconds, so I'm like, oh no, what happened. We are so sorry listeners. We just needed to make sure our guest Will was okay. Um. But it was that a firefly. It was a june bug or something what do they called. I don't know.

It was like I thought that was it's when you can like hear coming. Yeah, it looked like a bird to be honest. Yeah, it was gigantic. Well, it's so hot out and you're up in the shade, it's probably like, oh, this is nice up here. Like, oh wow, and he's a sports bug in my crew. What I do? I like Lebron. We didn't mean to laugh at year over there? Well, why don't you close this out? What is your number one pick for greatest sports moments? For sure? Honorable mention?

Jordan's kissing the floor at last game at Chicago Stadium was a Prome game, I believe. Yeah, it was like a primer, like a chair. It was it Pippin's Scary game. And my dad got us tickets. Awesome, So seeing that was pretty incredible. Uh. And the number one is oh second honorable mention, Yeah, as many great second mention, greatest sports year probably of my life is ninety. It ended

in mum the championship, the Bulls Championship. We won that, which was our final championship, the whole thing, the whole last dance basically that was that year. That was also my freshman year of high school and we won state championship for that as well. So I was like, oh, man, basketball, we're the I'm just around the best in basketball at all. Were you on the team? No, not at all excited. I tried out like everyone at school tried out because

quin Richon was our star. So like before the year before, they were on the news all the time because we won city but we didn't win state, and then everybody was like, oh, Hugh rich is gonna win state this year. He's got to win state. He's gotta be Corey mcgetty or whatever. But and then, uh so then freshman year, everybody was like, well, shit, if this is the biggest team in the country right now or city, at at least, they were like, we gotta play for the squad. So

the tryouts were like beyond belief. Everybody at the school basically tried out for the team. Oh my god, and nobody got it, but like a few people got his kid Najib was like, really good, he got varsity freshman year. Yeah, it was like it was huge. And so when we won that, it was huge. And then a couple months later the Bulls won, it was like basketball is the greatest thing ever. I'll never not watch it. I can't

believe I'm only watching winners. That's honorable. Mentioned the biggest was when I graduated grade and we had our party and uh and it was the night of our graduation party at Lenny Jones House. Was also the night we won the fifth championship, and so it was like the house I think was either on the south side or downtown. I don't know where the party was, but it was near where people were riding. So, like we won, everybody in the like no parents were there, so we all

started like I think they were smoking going on. I think there might have been drinking. I don't know. But then like everybody went outside and like we were just around people looting and we were like this is the greatest day of Like people were flipping cars outside like this is so and you were just like unsupervised eighth graders. Yeah, did you get to make out with anybody? I don't think so. I think I watched them pretty close. Yeah, I think. I never think when my team wins, to

go make out with something. No. I meant just because it's like eighth grade graduation, that seems like a makeout night, and then the game happens, it should have been a makeout night. I was not as cool as I am, you know what I mean? You got a woman pregnant, Yeah that's right, Yeah I was. That was a big deal. Did you did you loose at all? Did you flip anything?

You kick any mailboxes. I might have, like me and my buddies might have tried to kick some ship because we're like, you know, we're trying to be tough eighth graders. But yeah, it was like it was pretty amazing because it was the first time you could really like, you know, kids weren't really allowed to leave the house when the Bulls won because because of all the looting. But it was like, do you feel like you're growing up because you're going into high school and a couple of months

and you're like, I'm a man now. They're supposed to be adults. All the Jewish kids, they were just all their men, so I guess. So it was like it was huge. It was like growing up. I was like, oh, yeah, now I'm out with the looters. I'm out man. Yeah, a coming of age looting story. Yeah, I'm slipping. If the Lakers won't even though I've been a fan of them for two years, I'm gonna go flip a car.

He does, turn off, turn off the I had myself muted on the virtual fan, and so was like, turn on your mic, turn on your mic, and so I turn on my mic and then he goes go Lakers. I don't know. I'm gonna get kicked out of the damn PACER's virtual fan because my husband's a hater. That's the joy. That's what sports has become. Us yelling heckles into our laptop. We're doing it on Twitter. We're gonna virtually flip a car. Somebody to go flip their car and then they have to say, go lak. I'm gonna

burn all my masks. Oh yeah, I'm gonna burn all my masks. Yeah. And then I'm gonna take the ashes and I'm gonna make a new mask. All right. Well, well, thank you so much for spending an hour with us talking about Chicago. Um, stay safe, stay healthy, or anything we can to send our listeners your way. Oh at Mr will Miles on everything at Will Miles. And I'm

supposed to have a website soon. I haven't had a website ever, had one earlier and then somebody was like, hey, your website says you were voted one of the Brooklyn comedies people to watch Brooklyn Magazine and I was like, they were like, is that your biggest credit? I was like, oh, yeah, I should delete that website. Well you don't have to delete it. You can just update it, will I know, But I was like, that's done. Let's just start from scrap. Yeah,

you looted your own damn website. All right, we'll check out well on all that stuff. Check out of the shows he writes for south Side Side is coming to HBO Max. Yeah, congrats, that's awesome. Okay, we'll be on amc Uh there's another one, uh grownish grown Yes, I'm back in one. I wrote episode I think seven when

it comes back or something awesome. Hell yeah, I do all that and um you can find me at Better Megan Gailey on Instagram, Megan Gailey on Twitter, and I have started The Megan Gailey Bubble Machine, which is my show that's covering all things sports in the Bubble. I know. I didn't get a chance to talk about my virtual fan experience on here. We were just having so much fun talking ship. That's what I'm doing. You think I'm just mentioning it, don't, Megan Gailey the Machine, do not

watch it. I think you're just apologized. But no, I'm saying I'm gonna I'm gonna talk about it on the show. Oh my god. Now I know how you feel. Now I know how you feel um so yeah, I'm please watch it and be safe and wear a mask and be cute. And I'm at c J toldon and I do stupid things, okay, And thank you Ker, and thank you Sean too. Shout out to Sean and Will, thanks so much for being here. And thanks to um Kamala.

I guess I want to shout out Steve Kurt. Steve KURTA to go Steve when you're listening from one miles all right, that's been our show. We'll see you next week. The Greatest is a production of I Heart Radio. For more podcasts from my heart Radio, visit the I heart Radio app, Apple podcast, or wherever you listen to your favorite shows.