Brennan Lee Mulligan is one of the world's most beloved dungeon masters, and he joins Wayne and Jonathan to roleplay a prison escape, talk about how his players love to sneak in Austin Powers and Kendrick Lamar references into their games, and how D&D prepared him for his eventual career... in D&D! Watch this episode on Youtube! Follow Brennan Lee Mulligan on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Fol...
Jun 26, 2025•50 min•Ep. 17
The incredible Utkarsh Ambudkar, aka UTK (Ghosts, Pitch Perfect, Free Guy) joins Wayne and Jonathan on the Headgum couches to talk and spit rhymes about being "kinda rich", start (and end) beef with Kevin Hart and Kevin James, and dish about "Ghosts." Plus, an Andre 3000 fist bump story to remember! Watch this episode on Youtube! Follow Utkarsh Ambudkar on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Follow Headgum...
Jun 19, 2025•51 min•Ep. 16
James Adomian (Harley Quinn, Krapopolis, Jimmy Kimmel Live!) joins Wayne and Jonathan to perform an incredible medley of improvised impressions, including a scene where Bane and Blade meet in a laundromat. Plus Jonathan's surprise character cameo, Saturday morning cartoons, an Elon Musk rap, and more! Watch this episode on Youtube! Follow James Adomian on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Follow Headgum ...
Jun 12, 2025•55 min•Ep. 15
Drew Carey is a TV legend for hosting shows like "The Price Is Right" and "Whose Line Is It Anyway," but he's in the guest seat today! Wayne and Jonathan talk to Drew about seeing Phish live in Vegas, what people yell at Drew on the street, feeling your feelings as a man, and more! Watch this episode on Youtube! Follow Drew Carey on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Follow Headgum on Twitter , Instagram ...
Jun 05, 2025•1 hr 1 min•Ep. 14
Amir Blumenfeld (CollegeHumor, Headgum co-founder) inspires Wayne and Jonathan to write a song about NBA Jam, plus Shaq eating a twinkie, haunted hotels, and the secret room at Headgum studios dedicated entirely to liquor! Watch this episode on Youtube! Follow Amir Blumenfeld on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Follow Headgum on Twitter , Instagram , and Tiktok . Advertise on What If?! via Gumball.fm Se...
May 29, 2025•46 min•Ep. 13
Sam Sanders (Vibe Check, The Sam Sanders Show) joins Wayne and Jonathan to talk about craving Moo-Deng, shake-that-ass music, dating "I can fix you" type folks and more on a pop culture-recapping, freestyle-rapping, toe-tapping episode of What If?! Follow Sam Sanders on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Follow Headgum on Twitter , Instagram , and Tiktok . Advertise on What If?! via Gumball.fm See Privacy...
May 22, 2025•52 min•Ep. 12
The legendary LeVar Burton (Star Trek, Reading Rainbow, Roots) joins Wayne and Jonathan LIVE onstage in LA for the first-ever What If?! in front of an audience! From rap battles to sci-fi adventures to a hilariously off-the-rails game of trivia, this episode boldly goes where no episode of What If?! has gone before! Watch this episode on Youtube! Follow LeVar Burton on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. F...
May 15, 2025•1 hr 7 min•Ep. 11
Mary Holland (Ghosts, Nightbitch, The Big Door Prize) joins Wayne and Jonathan for a hilarious episode that includes hot tubbin', Mary flouting her flute-playing, the one word at a time game, Blumhouse horror parodies, Wayne gifting Jonathan his 40 acres, and a very touching story about a piece of toast who dreams of becoming a registered nurse! What If?! is LIVE at the Laugh Factory in Hollywood May 21! Tickets: https://tixr.com/e/137173 Watch this episode on Youtube! Follow Mary Holland on Ins...
May 08, 2025•56 min•Ep. 10
Anthony Veneziale, aka "Two-Touch", won a Tony Award as the conceiver and co-creator of the Broadway show Freestyle Love Supreme. Now he's bringing his improv talents to What If?! and dropping bars with Wayne and Jonathan! This episode has it all, including kiwi accents, vulnerable improv moments, and a special performance of TRUE, an improv game from FLS' live show! What If?! is LIVE at the Laugh Factory in Hollywood May 21! Tickets: https://tixr.com/e/137173 Watch this episode on Youtube! Foll...
May 01, 2025•55 min•Ep. 9
Greg Proops is a comedic genius, and he's also Wayne and Jonathan's guest on this week's WHAT IF?! ... From dishing on "Whose Line Is It Anyway?" lore to British Sayings to solving racism with improvised song, this WHAT IF?! has it all! What If?! is LIVE at the Laugh Factory in Hollywood May 21! Tickets: https://tixr.com/e/137173 Watch this episode on Youtube! Follow Greg Proops on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headg...
Apr 24, 2025•1 hr 2 min•Ep. 8
The hilarious Jessica McKenna (Play It By Ear, Dropout TV, Off Book: The Improvised Musical) joins Wayne and Jonathan for the most melodious episode of "What If?!" yet! From Kendrick Lamar style diss tracks to Myspace Les Miserables , this What If?! has it all! Watch this episode on Youtube! Follow Jessica McKenna on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Follow Headgum on Twitter , Instagram , and Tiktok . A...
Apr 17, 2025•1 hr 1 min•Ep. 7
Comedian and actor Carmen Christopher ("The Bear", "English Teacher") joins Wayne and Jonathan and gets visited by the ghost of Future Carmen-- plus Jonathan and Carmen's Italian connection, deep dishing about Chicago, and more! Watch this episode on Youtube! Follow Carmen Christopher on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Follow Headgum on Twitter , Instagram , and Tiktok . Advertise on What If?! via Gumb...
Apr 10, 2025•51 min•Ep. 6
Nicole Byer (Nailed It!) joins Wayne and Jonathan to experiment with autotune, dole out dating advice, and hit that high note from Wicked! Watch this episode on Youtube! Follow Nicole Byer on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Follow Headgum on Twitter , Instagram , and Tiktok . Advertise on What If?! via Gumball.fm See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://a...
Apr 03, 2025•46 min•Ep. 5
The hilarious Bobby Moynihan joins Wayne and Jonathan to talk (and rap) about Peach Snapple, the cookies at the DoubleTree, and the craziness of the SNL 50 reunion! Watch this episode on Youtube! Watch What If?! Live with special guest LeVar Burton at Dynasty Typewriter here ! Follow Bobby Moynihan on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Follow Headgum on Twitter , Instagram , and Tiktok . Advertise on What...
Mar 27, 2025•47 min•Ep. 4
Adam Conover receives “the best introduction I’ve ever received on any podcast” from Wayne and Jonathan, plus a secret organization of K.I.D.S., a jingle for Sammy Fingers, and a financial system based on sneezes and toots! Watch this episode on Youtube! Watch What If?! Live with special guest LeVar Burton at Dynasty Typewriter here ! Follow Adam Conover on Instagram and TikTok Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Fo...
Mar 20, 2025•47 min•Ep. 3
Colton Dunn (Superstore, Key & Peele, The Recruit) joins Wayne and Jonathan to answer "what if" a guest rapped their own theme song! Plus ‘street’ names, audition stories, and how “Whose Line” in Las Vegas saved Colton’s life! Watch this episode on Youtube! Watch What If?! Live with special guest LeVar Burton at Dynasty Typewriter here ! Follow Colton Dunn on Instagram Follow Wayne Brady on Instagram and TikTok Follow Jonathan Mangum on Instagram and TikTok This is a Headgum podcast. Follow ...
Mar 13, 2025•52 min•Ep. 2
Aisha Tyler joins Wayne and Jonathan to ask *what if* about life, the multiverse, margaritas, and everything! Plus, Wayne and Aisha talk "Whose Line," dating rumors, and whether they'd smash T-Pain! What If "What If?!" was your new favorite podcast?! Watch this episode on YouTube ! Watch What If?! Live with special guest LeVar Burton at Dynasty Typewriter here ! Buy tickets to What If?! Live in Austin on March 10th here ! Follow Aisha Tyler on Instagram Follow Wayne Brady on Instagram and TikTok...
Mar 06, 2025•58 min•Ep. 1
Wayne Brady and Jonathan Mangum are improv nerds! They’ve made stuff up for shows like “Whose Line Is It Anyway?” and “Let’s Make A Deal”, and now they’re bringing that same energy to the podcast world with WHAT IF?! On the podcast, Wayne and Jonathan invite smart, funny, and engaging guests from the worlds of comedy, science, & pop culture to have a conversation. The results are spontaneous scenes, songs, and riffs that explore the WHAT IFs of life, the multiverse, and everything! Improvisa...
Feb 27, 2025•56 sec
