Headgum
Wayne Brady's What If?! with Jonathan Mangum
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! Watch this episode on Youtube! Improvisation is a conversation baby! No script, no net, just WHAT IF?! This is a...
Be sure to visit the podcast's website and support the creator: art19.com
Where to listen?
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Episodes
JOEL KIM BOOSTER TEACHES US ABOUT THE BIRDS AND THE BEES 27.10.2026 1:12:34
Joel Kim Booster (Loot, Fire Island, KPop Demon Hunters) joins Wayne and Jonathan in the studio to talk about the birds and the bees, growing up gay in a religious household, and whether or not we’re currently living in a simulation. Whether it’s improvising a christian hip-hop song about the sex talk with your kids, being afraid of Gen Z, or playing a game of Superhero or Sex Act, Joel, Wayne and...
ELIOT GLAZER WANTS TO DO GAY HIS WAY 20.10.2026 1:21:11
Eliot Glazer (Broad City, New Girl, Younger) spends some time with Wayne and Jonathan discussing the right and wrong ways on how to be a “proper” gay guy. From his book, The Terrible, Horrible, No Good, Very Bad Gay, Eliot guides our hosts through the places every gay guy seems to vacation, how he navigated his first year out of the closet, and improvises a dating game show with three...
TIM BALTZ TELLS US THE SECRET TO AUDITIONING 13.10.2026 1:04:29
Tim Baltz (The Righteous Gemstones, Deli Boys, Widow’s Bay) drops by the studio to talk all things improv with the improv legends themselves, Wayne and Jonathan. Growing up in Joliet, IL, Tim spent all his free time taking the train into the city to catch an improv or sketch show at the Second City, only to find himself performing on the Second City’s Main Stage a decade or so later. From travelin...
DAN POVENMIRE GETS ANIMATED 06.10.2026 1:08:53
Dan Povenmire (Phineas and Ferb, Hamster & Gretel, Family Guy) spent some time in the studio with Wayne and Jonathan talking about all things animation! Since the age of 12, Dan always knew he wanted to draw. From his start on Teenage Mutant Ninja Turtles and the Simpsons, to his writing and animating days at Rocko’s Modern Life and Family Guy, all the way to creating his own hit show Phineas and...
PERSONAL TIME WITH WAYNE AND JONATHAN 29.09.2026 57:29
This week, Wayne and Jonathan spend some one-on-one time talking about friendship, betrayal, and everything in between. With the help of their audience, they improvise through a first date at the Griffith Observatory, sing about a heartbreak in middle school, and play wiki-roulette, where a random wikipedia page is chosen for Wayne and Jonathan to improvise songs based on that page (what exa...
BEN SCHWARTZ WILL NEVER STOP IMPROVISING 22.09.2026 1:20:41
Ben Schwartz (Sonic the Hedgehog, Parks and Recreation, DuckTales) joins Wayne and Jonathan in the greatest short-form, long-form improv set in What If?!’s history. Ben is no stranger to the improv world, traveling the country with his show Ben Schwartz & Friends where he, a couple of friends, and four chairs are all it takes to entertain a room full of people for two hours straight. Whether he’s...
CARTER VAIL WANTS YOU TO TAKE HIM SERIOUSLY...SOMETIMES 15.09.2026 55:16
Carter Vail (100 Cowboys, Dirtman) joins Wayne and Jonathan in the studio for a music filled episode you won’t want to miss. From Connecticut to college in Miami, to the musical streets of Nashville and Los Angeles, Carter takes us through his musician’s journey from going to school to become an audio engineer to discovering his love for comedic (and serious) songwriting. Join them as Carter teach...
ANGELA GIARRATANA TEACHES US HOW TO RESOLVE CONFLICT 08.09.2026 1:00:32
Angela Giarratana (Smosh, Dropout, Starkid) drops in on Wayne and Jonathan for an episode filled with music, laughter, and a whole lot of conflict resolutions. Join them as Wayne talks about a real life street fighter moment that ended in handcuffs (but was it him or the other guy??), Angela recaps her most memorable “Am I the a**hole” scenario on Dropout, and how she prefers to handle conflict (t...
ZACH ZUCKER AND VIGGO VENN WANT TO CLOWN AROUND 01.09.2026 56:37
Zach Zucker (Stamptown) and Viggo Venn (Britain’s Got Talent) spend an afternoon clowning around with Wayne and Jonathan. After meeting at a clown school in France, Zach and Viggo quickly became good friends, venturing into comedy together. Sit down and get intimate as they talk about their journey through the comedy scene, their love for the stupid and dumb, how clowning changed their lives, and...
EDI PATTERSON PROVES LAUGHTER IS THE BEST MEDICINE | What If?! with Wayne and Jonathan 29.08.2026 1:01:38
Edi Patterson (The Righteous Gemstones, Vice Principals) joins Wayne and Jonathan in a laugh-out-loud interview as she reminisces about a British school teacher she once had in rural Texas, a surprise visit from her popular character Beandip, some improvised infomercials, and an in depth conversation about her iconic and beloved character Judy Gemstone and her time on the Righteous Gemstones. FOLL...
MORGAN JAY TEACHES US HOW TO PROPOSE | What If?! with Wayne and Jonathan 18.08.2026 48:45
Morgan Jay (Hulu, NBC, and Comedy Central) joins Wayne and Jonathan in a hilarious and very musical interview as he sings to us about his “chill proposal” to his girlfriend, an improvised song about how to make a proper pretzel, a story about Prince and an intimate after party, and a proper rizz-off with a musically talented audience member. What If?! will be LIVE at Dynasty Typewriter in Los Ange...
What If Doug Benson Was Our Guest?! 03.07.2025 57:09
Doug Benson (Doug Loves Movies, Super High Me) joins Wayne and Jonathan for a hilarious What If?! sesh! Doug talks about getting stoned with his fans after shows, doing prop comedy with Judd Apatow in the Valley back in the day, how he almost became an entertainment journalist, and more! Watch this episode on Youtube! Follow Doug Benson on Instagram Follow Wayne Brady on Instagram...
What If Brennan Lee Mulligan Was Our Guest?! 26.06.2025 50:09
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 B...
What If Utkarsh Ambudkar Was Our Guest?! 19.06.2025 50:30
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&nbs...
What If James Adomian Was Our Guest?! 12.06.2025 55:20
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 ...
What If Drew Carey Was Our Guest?! 05.06.2025 1:01:03
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&n...
What If Amir Blumenfeld Was Our Guest?! 29.05.2025 46:13
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 &...
What If Sam Sanders Was Our Guest?! 22.05.2025 51:34
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&...
What If LeVar Burton Was Our Guest!? (LIVE at Dynasty Typewriter) 15.05.2025 1:06:31
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...
What If Mary Holland Was Our Guest?! 08.05.2025 55:53
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 Holl...
What If Anthony Veneziale Was Our Guest?! 01.05.2025 55:11
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...
What If Greg Proops Was Our Guest?! 24.04.2025 1:01:52
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...
What If Jessica McKenna Was Our Guest?! 17.04.2025 1:00:37
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 Foll...
What If Carmen Christopher Was Our Guest?! 10.04.2025 50:35
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 In...
What If Nicole Byer Was Our Guest?! 03.04.2025 46:04
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 Twi...
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