Hey there, stranger! Come on in! This week’s guest is the supremely talented Annie DiRusso! Annie and Caleb talk about going on tour together, the life of an indie musician, their student council days, the return of earnestness, the biggest mistakes you can make on a date, and much more!
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Joi ... Show More
Nov 20
Maggie Winters Sees the Comments
<p>Welcome! This week’s guest is the hilarious Maggie Winters! Maggie and Caleb talk stories from the road as a touring comic, a return to cringe as a nation, fast food optimization, her new podcast, and so much more! </p><p><br></p><p>Join our Substack for an exclusive post ... Show More
59m 38s
Nov 13
Zach Zimmerman is Not Evil
<p>Welcome! This week’s guest is the hilarious Zach Zimmerman! Zach and Caleb talk moral dilemmas, parental expectations, good vs. evil, praise, so much more! </p><p><br></p><p>Join our Substack for an exclusive post-episode chat with Zach and other bonus content! http ... Show More
1h 5m
Sep 17
Bonus Episode: Try Hard with Erika Casupanan
<p>Today, we’re bringing you an episode of <a href="https://podcasts.apple.com/us/podcast/try-hard/id1824016771"><strong>Try Hard</strong></a>,a new podcast hosted and produced by one of our very own dowager queens of gossip, Alex Sujong Laughlin.</p><p><br></p><p>This episode is ... Show More
38m 24s
Jun 2025
#290 Subtlety Is Not On The Agenda with Caleb Hearon
<p>Our first 4th time guest Caleb Hearon joins to humble Gianmarco, and explains why you shouldn't be in New York City if you can't live with some noise, examines the death of passionate male friendships, what it takes to fight back against evil landlords, and why entrepreneurs h ... Show More
1h 40m
Aug 5
#300 A Happy Trail to Nowhere with Emil Wakim
<p>Comedian and SNL cast member Emil Wakim joins to share the downsides of facing the angry Internet mob after your first Weekend Update, what it's like to give your thighs a fade, becoming a bidet guy, going to war for Sydney Sweeney, and why BS coffee shop orders have gotta sto ... Show More
1h 38m
Aug 19
#304 Outed by God with Josh Sharp
<p>Comedian Josh Sharp (<em>Dicks: The Musical</em>) returns to share the downsides of being the king of PowerPoint comedy, cruising Craigslist in a pre-Grindr world, coming out as a result of divine intervention, and why tendinitis has gotta stop.</p><p><br></p><p>Follow Josh Sh ... Show More
1h 33m
Aug 23
#305 Hot Sex-Ed Teacher Taught Us Absolutely Nothing (Patreon Excerpt)
<p>In this Patreon excerpt, Gianmarco and Russell share the downsides of not learning anything in sex ed class, and the different ways of presenting @$$. Watch the full episode exclusively on Patreon, and join for only $5 a month! <a href="https://www.patreon.com/downside" r ... Show More
15m 7s
Feb 2025
Bonus Episode: Life as a New York Times Bestselling Author with Kelsey McKinney
<p>Popping into your feeds with a little treat! In today’s bonus episode, Kelsey joins Rachelle to answer all of our burning questions about her new book, <em>You Didn’t Hear This From Me: Mostly True Notes on Gossip, </em>reality TV, victorian marriages, and, you guessed it, gos ... Show More
39m 9s
Aug 12
#302 Unsolicited Hole with Alex Edelman
<p>Tony-Award winning (and return guest) Alex Edelman returns to share the downsides of getting unsolicited hole pics, doing a Broadway fundraiser for Joe Biden, the challenge of writing a one-man show, and why w33d emporiums have gotta stop.</p><p><br></p><p>Follow Alex Edelman ... Show More
1h 42m