Chelsea Handler on Real Talk, Resilience, and Reaching 50

Hello Sunshine, Hey, besties. Today on the bright Side, it is the one and only Chelsea Handler. You know her from her late night shows and her multiple New York Times best selling books. She's out with a brand new book called I'll Have What She's Having and a brand new Netflix comedy special.

It's Thursday, February twentieth. I'm Danielle Robe.

And I'm Simone Voice, and this is the bright Side from Hello Sunshine. Danielle, you sound like Sunshine today, Sunshine.

Indeed, you know I caught the flu, Simone.

I'm so sorry, thank you.

I'm actually okay, but my voice does sound a little wonky, So I'm so sorry about that.

Oh no, please don't apologize. I was right where you are, I want to say, like three or four weeks ago.

So it's gonna get better. It's gonna pass.

Yes, it's going around. It's crazy. Everybody I know is so sick.

I don't know.

I kind of like this new voiced in Yelle. Maybe you should like try to keep it. It's like kind of sexy.

It is sort of sexy and masculine in some ways.

Wait, I'm trying to think of like I need you to say, like a phrase. Can you say, like, come hither, M I just want to hear how it sounds.

Come hither.

Oh my god, Oh my god, Danielle, that's so good.

Yeah, well, coming hither today to our show is the one and only Chelsea Handler Simone. I have been a fan of Chelsea ever since I was a little kid, Like she has been on my interview vision board for years.

Okay, So what is it about Chelsea that you feel like so attracted to? Like why was she on your vision board?

Because she's so unfiltered.

I feel like she says the stuff that you're not supposed to say out loud. She says the quiet part out loud a lot, and whether she's talking about sex or politics or celebrity culture, she just never cared about being liked.

It was always about humor.

And the truth, and honestly, sometimes it was ruthless, but it was always sharp, you know.

And I just I so respect that.

I'm not like that, I'm not gonna say the quiet part out loud, and so hearing her say it was just so inspiring to me.

I so agree with you.

And I also feel like she was really ahead of her time in that sense, like just having that courage to be so unfiltered in a world that felt so proper and curated. She really has always led the way.

You're so right.

She redefined late night TV in my opinion, because before Chelsea, it was such a boys club. And she was one of the very few women to host her own late night talk show, Chelsea Lately. And she did it without trying to fit into this male dominated format. She did her own thing. She talked about pop culture in a smart way. I feel like she paved the way for a lot of women in comedy completely.

Also, late night is still a boys club like I would love to see Chelsea back on primetime airwaves.

Oh yeah, can we start that petition?

Seriously, seriously call your congress person. We're getting Chelsea back on late night.

Simone. You can't make me laugh, not with this voice.

I'm so sorry.

I will.

I'm gonna do this just completely straight laced.

Okay. Well, missing this interview was a bummer for me, but I can hear just how thrilling this was for you. So I'm so happy for you that you got to check this one off your vision board and I can't wait to listen.

Simone.

You were missed for sure, and I think you and the listeners are going to be surprised by this conversation.

A lot came out.

We laughed, we cried, and we definitely talked about her new book that's going to be out soon I'll have what She's Having, And in it she chronicle stories of her life that detail the woman she wanted to be, the woman she became, and the woman that she is today on the cusp of turning fifty. So here's my conversation with Chelsea Handler.

Chelsea Handler, I'm so excited to say this. Welcome to the bright side. Hi, congratulations on your new book. You're about to break into this totally new chapter of your life. And I read that you're intentionally releasing your seventh book, I'll have what She's having on your fiftieth birthday.

Yeah.

Yes, So you wrote in the book that you can't believe that you're alive at fifty.

You have to tell me why. Well, I mean for obvious reasons. I mean, if you know anything about me, you know that I push it real hard. I never imagined that I would be fifty. I remember knowing my dad was fifty two. I think my dad had a heart attack when he was fifty two and I was like, oh, I guess it's.

A wrap on him.

And then he came home from the hospital and lived another thirty years. But now, like fifty years or well forty years later, fifty.

Is not what fifty used to be.

Like, I am pretty psyched about turning fifty. I'm pretty psyched that my life is like this at fifty, and I'm pretty excited about all the decisions I've made.

I want to ask you all about that because I've read all your books and it was so different. It feels like you took this step back and zoomed out on your own life from this bird's eye view and examine the choices, the heartbreak, the defining moments. And you've been really vocal about all the therapy. But after examining the woman that you became, did it match up to that vision that you had as a little girl.

I think it did.

I think it took me a long time to try to remember what all of these visions I had of who I would be when I grew up, Like as a little girl, I think we're always like, this is the guy I want to be, This is the woman I want to be, This is the type of person I want to be, but we kind of always lose sight of that along the way. Life gets in the way and we're hustling, we're trying to achieve something.

I remember moving.

Out to LA when I was nineteen years old, and I just wanted to like make it, but I didn't know what I wanted to do. I just wanted to be someone that people knew, but I didn't know what my talent was, so it was pretty like shallow aspirations.

It was like, oh, I basically wanted to be famous, but.

As I started to pursue that and doors would either shut or open, you get into an avenue. And the avenue I ended up in was stand up comedy, which really allowed me to express myself without an editor, which allowed me to build an entire career just off of being myself, of my personality.

And I had no idea when I was a little kid that that was even something that you could do.

But the overarching theme, I think when the book starts out with this letter of me as a young girl like kind of envisioning what kind of woman I wanted to be, it was more about like.

The spirit of who I was going to be. I was going to be bold, and I was going to be brave, and I wasn't going to follow people around. I was going to be a follower. I was going to be a leader.

I was going to stick my neck out, I was going to say the thing that nobody wanted to say.

Like I really wanted to just be a great sister to the world.

And I have two great sisters, and I I grew up like in a very loving sisterly vibe, like my.

Friends are my sisters. Strangers that are women are my sisters.

And I think the biggest theme that I always wanted to embody was being a sister. You know, in my early career I would be more of a bully. I was more of like this is how I see I'm the cool chick. And then you grow up and you're like, no, no, no, that's not cool. You know, being cool is being like a lover to everyone. You know, you don't have to be the most popular, you don't have to be the coolest.

It's not about that. Being cool is.

Being really just great to everybody and giving everybody a chance.

I love that you said sister to the world because there's this huge emphasis in the book of really just supporting women. And one of my favorite stories is something that you call the pocket full of Sunshine story.

Will you share that?

Yes.

I was at the Montreal Comedy Festival just for laughs, which when I was coming up.

Was the thing.

It was the festival that meant you were on your way, that meant you were like gonna make it or you were close to making it. And I was in my late twenties and I went and I did a showcase and there was all this buzz about me, and I was like, Okay, this is my moment, like I'm getting hitting it, like all the executives that were important were going.

To be there on that night.

And then I bombed badly, like eight shit. And I remember zach Elifanakis walked me to my hotel room after I was mortified, and he was like, you're just gonna have to be alone and deal with this. It's going to be pretty upsetting. This is part of the industry. And I was like, no, this isn't part of the industry.

Because it's not like you to bomb, right, No.

But again I wasn't.

I was like in a moment where I got caught and swept up in my own kissed and vinegar, like it wasn't real because I got all this buzz about me instead of remaining grounded and like in my body, I got swept away in the moment and I was grounded, and I and the lack of reaction at the top, I just was like I was very young, you know, I was like twenty seven or something, so I just wasn't as seasoned as I am now. So it threw me off, and then it threw off my whole set, and then I sped through my set.

I thought my life was over. I really thought, Okay, now I have to think about what else I can do for a career, or am I gonna have to get married? You know what I mean? Like what happens now?

And then I went back to LA and I had another show the next night in Montreal, but no one came to that because everyone had seen me bomb.

And then like this girl's not ready, she's not up his phone.

And then I got to LA and my manager said there was one executive that had not been at the showcase.

Her name is Grace who she used to work at NBC. I don't know if she still does.

And he said she wants to come see you at Luna Park on Tuesday. She's the only executive that didn't see the showcase. And I went to Luna Park and I did the same exact set, and I crushed it because now.

Everything was off the table. The next morning he called me and said, Okay, they want to give you a development deal for your own TV show for one hundred thousand dollars. And I thought I had hit the jackpot.

Like it was just the span of events, like it was a seventy two hour span, and within that seventy two hours, what I thought was over was born again. So I share that story in the book because I want everyone, whether you're in the entertainment industry or not, to know that every failure has a rainbow around the corner.

My corner was really quick, but that's how quickly things can change in your life.

You said that you call back on that story during hard times, and if you're willing to share, I'm wondering when the last time you needed that story was?

Oh, all the time? I mean I always need.

I mean I had a pretty rough year in terms of stuff I'm dealing with this house I'm building, it's been pretty icky. Like what's gone on, stuff that's happened, and I can be really positive and have a good attitude every morning, and then it's kind of like you spend your day just getting tossed around and knocked over, and.

Then by six o'clock you're like, I fucking give up.

I'm gonna fucking take a xanax, go to bed, and I'll try again tomorrow.

Because this positivity thing isn't working.

But you have to remember in those times, I always look at that experience whatever difficulty I'm having, is like in the times where I don't feel confident, where I don't feel strong.

To remember that there is a version of you that does and they're not that far away.

It's so important to have that in your back pocket because if you can't call on it, you never get back up. I feel like a lot of women in comedy owe their career to you in a lot of ways. Are there any people whose careers you feel like you had a hand in that you're particularly proud of. I don't.

I would never give myself credit for well.

I mean, I had a hand in a lot of people's careers because they were on Chelsea lately.

But I was just recognizing talent.

That's something that a lot of It takes more than one person to recognize that talent.

I can give them an open door.

But there's nothing that gives me more pleasure than introducing someone to the world, especially another woman.

And that was the beauty of Chelsea Lately. I could book.

Whomever I wanted, and if you were an underdog, if you were remedial, if you were weird, you were on the show like that made you more welcome, Like we were doing DEI before DEI was a thing. That is the nature of who I am. I want the hunderdogs to succeed. So with Fortune, I just took one look at Fortune and she said one thing, and I was like, I was in love with her, And ats going with another humongous talent.

Yeah.

No, I think I'm just good at recognizing talent. I'm not the reason they're talent. They're successful, but I definitely recognize their talent for sure.

At the beginning of our conversation, you said you had this idea of who you wanted to be and that you were going to be defiant. To me, that signals like you had this inner voice before you even maybe knew what an inner voice was, And there's a lot of stories in the book about how you were a dream chaser and a go getter even ten eleven thirteen. I mean, you were reading Tolstoy, you were buying first

Yeah, for sure, every single minute, even the pain, you know, like the pain I would.

Bring around again.

Maybe I would have been a little bit more you know, responsible and more careful about you know, less hurtful to others.

At certain times in my life. I would try to.

Be more mindful of that. But I also think it's the engine that gets you where you need to go. I think I talk so much about my younger life and being a young person because I really believe the essence of who we are is really at its.

Peak when we are children before the world, you know, besmirches us, before we are thrown around and fall down so many time.

It's like the true essence of who we are before we face any challenges, is the person we want to keep going back to throughout our life, Like that little inner child that's who we really are, and that's never a bad person, you know, that's always a good person.

And it's always good to kind of check in with yourself, like how am I doing?

Would I be proud of me as a seven year old? Would I look at myself today and be like, I'm proud of you? And the answer is fucking.

Yeah, Like, yes, I'm fucking proud of you. You're crushing it.

You did so much of what you said you were going to do, and then some there is a moment in the book, though, where you're not so proud.

Can I share it? Sure? Okay?

So you go to Jane Fonda's house and it's kind of a surprising invitation. You're at a party and she calls you after the party and she's like, we got to talk. You made people at the party uncomfortable and you were like so taken aback that Jane Fonda called you out, which understandable. Is that the first time that you were on the other side of brutal honesty? Yes?

Is that why it hurt?

It hurt?

But I got to say I took it like I took it like a man. I was like, whoa you want to be honest with me. I'm known for my honesty, so I've got to be able to dish it and take it.

And moreover, I knew in that moment, A.

She was never going to have to speak to me again about my behavior, like I would make the first time the last time. And B that was an example of sister like. She showed me what it was to be a sister to another woman. She did not have to take the time to invite me to her house, she did not have to spend time with me. She went out of her way because she cared about me, and that became a roadmap for me with my relationships with other women. She had the difficult conversation which so

And that just had such meaning for me.

What was the truth? What'd she say? The truth was that I.

Was acting badly at her party. I was just like arrogant and I was on drugs. I don't even remember what drugs, but I was just in a dark space. You know, you're not grounded and you're kind of flighty and you're and then you add drugs or alcohol to the equation, it just becomes ugly. It's not positive, it's negative. And that I was in the phase of my life where I was just very angry and kind of arrogant

And I'm like, oh no, no, I'm going to spend my life I've proven to you.

Vers That's so sweet. That's such a good full circle moment.

It was because also I've had so many girlfriends in my life, and so many of them, you know, whether it's harmless or not. Not a lot of people do that. Not a lot of people tell you the truth even when you ask. Yeah, And I think we are really like in a deficit of truth.

And I think truth is so powerful, it's so bonding, and it's so necessary.

So I just always want to be truthful, especially with women.

We need to take a quick break, but we'll be right back. Stay with us and we're back. I remember watching you on Chelsea Lately. You had this unshakable confidence, and so I was so surprised in the book to read that when you went to the Netflix show you felt like you had lost it. You describe it as like lou and Gas was was it a personal thing or what was happening?

It was a bunch of things. It was a personal thing.

I had never been to therapy, so I had never discussed my brother dying when I was a young girl, So there was a lot of delayed grief. The first Trump presidency, I had a really angry reaction to that.

I couldn't even believe that would be possible.

And all of those things combined just kind of like, you know, things worked for you until they stopped working for you.

All of my botto and all of my kind of no bullshit attitude.

All of that stuff really really worked for me until it did it, And then all of a sudden I was like, wait, I'm getting nervous, I'm not grounded, I'm insecure, I'm having all these weird thoughts.

I wasn't sure of myself.

I went into therapy and it was the best thing I ever did, even though it took a long time, but I realized, like, oh, there's a better more, there's a cooler version of me. There's like a two point zho Like the gift of self awareness is like the best you have you can give yourself, and that's what therapy is.

Did it change your comedy too? Yeah?

I did.

And the best way, you know, it just made me more present as a person.

I used to go on stage and be shit faced or not.

I have two shows in one night and not even remember that in a second show it was such by octane that I had to stop and calm down and really present and be mindful of everything I was doing and actually being on stage and enjoying the fact that people are paying money to see me and showing up

Was there a revelation that you had in therapy that, like, even to this day is hard to sit with.

I mean, I think one of the revelations was like, first of all, not everybody's interested in your opinion.

I'm like, what didn't believe that?

I was like, my opinions pretty spot on, Like why wouldn't anyone be interested?

And also that I don't have to be like the life of the party.

That was the biggest because I would I left therapy and then I'd go to parties or dinner parties, and I'd kind of like audition this new personality of mine and I'd sit back and be quiet and like not talk or not insert myself into conversations, and people would be like, what's going on with you?

I'm like, I'm in therapy. I can't talk right down.

People would be like, well, this isn't fun, Like we want the real Chelsea back, and I'm like, I don't know where Chelsea is.

Like did you lose any friends?

Yes, yes, totally.

I had to start hanging out alone because I didn't know who I was. You go to therapy, you get all this information, then you have to absorb the information and then you have to apply the information, and that is a lengthy, arduous process. So throughout that process, I was constantly being like, is this who I am? Is this who I am? And you know, through like what most people go through in their teenage years, I went through in like my forties.

I think it's a cool time to go through it.

Yeah, I mean now it is because it's over. Yeah, so that's good. I mean everything's good.

When it's over, You're like, uh, okay.

So one of the things that I've always looked to you and admired is that you're never afraid to walk away, and that's hard for most people. You walked away from a Netflix show, you walked away from a long running talk show on e I'm curious if there was ever a time where you feel like you should have walked away and you didn't.

Yeah, relationships, of course, friendships definitely.

But again, like I don't sit and I don't getmired in the past, because a what's the point. These are the decisions we've made and there's nothing you can do about it, and if anything, it's a learning tool for the next situation you're I like every lesson to be the first time and the last time. I don't want to learn lessons twice. I'm not going out with a narcissist twice.

That's only goods.

You know.

I'm not gonna like make big blunders in my life twice. I'm smart. I'm too smart for that.

So I'm a good student and like in this in the learning, like a student of life. I get it. I'm like, Okay, I got that message, yeah and clear. And I don't think there's a big point in thinking about what you could redo or not do. And I think that is one of the most beautiful things about being this age is that you're not worried about the past.

You're not worried about the future. I've got me.

Like, and you know that because you're you've been with this person this whole time. It's like when people are insecure or unsure they're footing, it's like, look, who got you here?

You do?

I love that. That's really beautiful.

We have to take another short break, but we'll be back in just a minute.

Don't go anywhere, and we're back.

This is the portion of the interview where I'm asking for a friend because I am thirty four not married, and I've always looked to like I remember reading about Gloria Steinem's life and thinking like, that's so cool that she had all these like six seven year relationships with lovers. So I'm very curious about your perspective on relationships. You wrote in the book, I want to connect with a man in a way I haven't yet.

What's an example of that? What does that look like to you?

Because I feel like you've had all these really interesting connections.

Well, my current lover said to me the other day, and this isn't maybe what you're saying, but he said something that was so like he so sees me right, he sees life.

He's not in my for a public life, professional life, but he's in my life and he sees how hard I work.

He sees like how much I show up for my friends, how much I show up for my family, And he really values our time together. He always says, how much time I deb with you. I just want to as much as I can get. And I'm like, that's so sweet. But I it feels and he's not an ego, Like there's no ego with him, and it feels so sweet to be seen in that way is not a threat to a man, not as an emasculation to someone. And he said this the other morning we woke up and he was like, you know how lucky I am to

And I just said, what man thinks that? And then says it? And I thought, Oh, I'm finally.

Being seen for who I am because I have no attachment to a relationship. You know, you bring me in all things you do when you finally let them go.

I saw this post years ago that you made about your parents. It was like this old black and white photo and you said my parents were in deep throes.

Of love with a bee.

We all deserve to be in love, but love is even better because for me it means family.

Is it love? Do you feel love with this lover?

He's a lover? Yes, I feel love with him for sure. Yeah, But I like, listen, I love everyone, So is it love?

Like?

Is he the love of my life?

No?

Probably not?

Maybe I don't know. I don't think so. But there are so many loves in life.

You know what I mean?

Absolutely and I want I want exactly what you're talking about with Gloria Steinem.

I want lots of lovers.

And I've had lots of loves and I'll continue to you know, like that's that's the kind of life I want.

Well, I've read impast interviews and this could be pre therapy that you sometimes felt like you couldn't be your best, most ambitious self in partnership. This is something my friends and I talk about all the time. So many of us feel this way because I think men require a lot.

Has that changed for you at all?

Yes, it has, because I am just who I am now. I don't have any.

I'm not trying to impress anybody. You're either impressed or you're not. Like I'm not trying to coast up to some guy. Guys are trying to be with me or not. I'm not the answer.

I don't care. I have no attachment to being in a relationship or being married. And when you have that attitude, that's very magnetic for some reason, and it has to be true. You can't just say you don't care. You have to really not care.

So hard to really not care, I know, But once you get that feeling, you don't get out of it. Yeah, once you don't care, you don't go back to caring again. So it's just something that's aspirational. And I don't think it's supposed to happen at your age. I think it happens as you age.

Okay, thank you for that. That's a good thing to look forward to. Yes, Okay. In the book you say that the reason to have a partner or children shouldn't be so that they can be there to watch you die. I look forward to either paying some nurse or drug dealer to put me down like a horse or help usher me out of the world with a large dose of morphine.

Incredible, what a revelation. It's so true.

Yes, I mean, I'm still looking into euthanasia prematurely, like I don't really want to get old. Somebody said, if you can get through the next fifteen years, there's going to be so much science and innovation that you'll be able to live until you're one hundred and fifty, And I'm like, well one hundred and what I don't and do you stand up, like, what is my vocation at one hundred and fifty?

I can't afford to live.

Until I'm one hundred and fucking fifty on Mars like, no, I'm not interested. I want to do a group US in Asia with a group of friends at some point who are like minded.

I thought it was so funny because everyone talks about that they don't want to die alone, and you're like, it's ridiculous, who cares.

No, I'm happy to die alone.

Also, yes, absolutely, I had to have shoulder surgery two weeks ago and I was being put under. I'm like, if you want to give me a couple of extra doses, I'm good.

Like, I'm I'm I have a lot of big We need you. I'm like, wouldn't be sad. I'm like, I love my life. I've had a great time, but I'm also exhausted.

No, no, we need you. There's so much more for you to say. I want all the opinions. I have one last question for you, because I love hearing stories about your family. And you make fun of your dad constantly for being a you cars salesman and being ridiculous as you say. You make fun of your siblings, You make fun of your bosses while they're still your boss.

Yeah, yeah, I think she would be.

She was so different than me, and she was so so spoken and so quiet, like she didn't know what the fuck I want. My mom was always just kind of she just didn't know what to do with me. And then once I started to get and more mature, she was like, oh, She's like you're She's like, you have so much to say and you have so much to share. She's like, I think your frustration at being a child was because you had.

No agency and you just wanted to grow up. And I did.

All I wanted to do was grow up. I didn't want to be a baby. I was like, I felt like a woman. I'm like, I'm a woman. My dad's like you're four. I'm like no, I feel like a woman, Like I can go out and I just always had that independence, and my mom really recognized that in me and understood that we were so different and that I needed to like fly away.

And when she was dying, she said the sweetest thing to me.

She said, I know you're going to have a really big life, she said, and I need you to take care of your sister and your brother because they're going to need you. And I know you're going to like meet all your goals and you're going to be wildly successful, and you're going to see the world.

And she's like, I won't be here, but I'll be there.

And so I always think of my mom when I'm going on not to like hit the stage to do something big, or before I perform, I always just like look up, and I just envisioned my mom like dancing around the ceiling.

So she is always with me. So I'm glad you brought that up, Chelsea.

I can't believe you made me cry.

They may cry.

That's really sweet, really really sweet. Okay, I can't end on this note, so you have to make me laugh. I years ago read in some random magazine somebody asked you a beauty product that they would cry out of your cold dead hands, and it was like this seventy dollars moistureizer that I could not afford at the time and bought anyways because you said it. So now I need to know what is the updated version, What do I need to buy?

And what can I cry out of your cold dead hands?

Do you have oily skin or dry skin?

A combination?

I love liz Earl serum.

I love like oil serum because I'm very dry, so I constantly need lubrication, hydration and serum.

But if you have any oily skin, it's not the same. It doesn't work for you.

But what what could you not fly? I mean lip balm. Lipbom is the bomb. I use that under my eyes. I put it on my face when I try like it's a I put it in when my hands are like dry.

Put it on my hands like that is bazzling Lipbom. I have a tube of that wherever I go.

That's a good one. Thank you so much for joining me.

Thank you, it was such a pleasure. I had such a great time with you.

Thank you for that.

Chelsea Handler is an author, comedian, and TV host. Her latest book, I'll Have What She's Having, is out next week February twenty fifth, and her comedy special Chelsea Handler The Feeling is out on Netflix next month.

Well that's it for today's show. Tomorrow, we're popping off on the biggest pop culture moments of the week with comedian and content creator Rachel Samples. Join the conversation using hashtag the bright Side and connect with us on social media at Hello Sunshine on Instagram and at the bright Side Pod on TikTok oh, and feel free to tag us at Simone Boys and at Danielle Robe.

Listen and follow The bright Side on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

See you tomorrow, folks, Keep looking on the bright side.