Sam Morril
Oct 18, 2026
Sam Morril (We Might Be Drunk podcast) takes his shoes off for the 5th time. However, this is the first time he's been on TYSO on the East Coast! Check out his new special INCORRECT, on Netflix…
Hi, I'm Rick Glassman, and I'm a goofy guy and a cute boy. As a kid, I had debilitating OCD. I still have a lot of “things.” The title of my podcast “Take Your Shoes Off” is a microcosm of my need for control and order in a world that... keeps their shoes on. I created this podcast to showcase a more serious side, as I have conversations with some of the funniest and most interesting people in the world. I’ve learned the language of comedy in an attempt to survive this shoes-on world, so of course there will be some goofs and spoofs, but think of this podcast as you being a fly on the wall, as opposed to being an audience member in a theatre. Please, take your shoes off, and enjoy!
PodSkip has analyzed 5 episodes of Take Your Shoes Off w/ Rick Glassman, averaging 11.0 ads per episode (7% of runtime).
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Are You Garbage (H. Foley & Kevin Ryan)
Oct 08, 2026
The Are You Garbage boys take their shoes off for the third time to be funny and talk about three new special, AMERICAN GARBAGE.🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in your city…
Lily Phillips
Oct 02, 2026
Lilly takes her shoes off in London to talk with Rick about poop and pee and stuff. TBH, you don't have to watch this episode. See you next week.🎟️ Find out when RICKY’S ON THE LOOSE is doing his…
Romesh Ranganathan
Sep 27, 2026
A new Sleepover Series in London, baby. While Ricky's On The Loose (stand up tour), Romesh comes to a show. Then Ricky goes on The Romesh Ranganathan Show…
Rick tour self-promo, Instant Hydration sponsor read
Jeremiah Watkins 3.0 (Feat. Special Guest)
Sep 18, 2026
Jeremiah Watkins takes his shoes off. Okay? Watch it or don't. But make sure to check out his new comedy special: Jeremiah Watkins: Crazy Pizza | Official Comedy Special…
Rick tour self-promo, Progressive boat insurance ad
Ike Barinholtz
Sep 09, 2026
Ike Barinholtz is best known for being the guest on episode 371 of the Smartless Podcasts... until now! Ike takes his shoes off for the first time on episode 371 of Take Your Shoes Off with Rick…
Progressive boat insurance ad, Hims hair loss / Factor Meals mid-roll ads
Mark Normand 8.0
Sep 05, 2026
Another sleepover series. NYC edition. Mark Normand (We Might Be Drunk podcast) takes his shoes off for the 69th time (iykyk).🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in your…
Progressive truck cargo coverage ad, Progressive boat insurance ad
Pete Holmes 4.0
Aug 27, 2026
Pete Holmes takes his shoes off for the fourth time to get stoned with Rick and talk about stuff. Check out his new special on YouTube, Silly Silly Fun Boy here…
Rick tour self-promo, PrizePicks ad
Dave Franco
Aug 20, 2026
Dave (short for David) Franco takes his shoes off for the first time to talk with Rick about movie trailers and even more stuff. Check out his new movie, IDIOTS, August 28 and FORGOTTEN ISLAND…
Kevin Heffernan & Steve Lemme (SUPER TROOPERS 3)
Aug 11, 2026
The boys take their shoes off for the 3 time to talk Supper Troopers 3!🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in your city: https://www.rickglassman.com📍 Upcoming dates:🗓️ Aug 9–13 •…
Magnus Ferrell
Aug 05, 2026
Magnus Ferrell takes his shoes off for the first time to talk about his music and to play some music (with a special guest?). Magnus has been popping off after his music has been circulating online--…
Zoey Deutch
Jul 28, 2026
Zoey Deutch takes her shoes off to talk with Rick about stuff. You wanna write a description more accurate than this? Give it a try. In the meantime, go watch her new comedy (directed by TYSO Alumni…
Jake Johnson 2.0
Jul 24, 2026
Jake Johnson (New Girl, Tom Cruise) takes his shoes off for there second time.🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in your city:https://www.rickglassman.com📍 Upcoming dates:🗓️ July…
Jason Alexander and Peter Tilden
Jul 15, 2026
Jason Alexander (from Shallow Hal and Seinfeld) and Peter Tilden make a rare podcast appearance as they take their shoes off to talk with Rick Glassman about stuff. Check their REALLY NO REALLY…
Adam Ray [28th Appearance]
Jul 08, 2026
Adam Ray takes his shoes off for the 28th time to get stoned with Rick and be friends. Check out The Adam Ray Show on Netflix now.🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in your…
Lisa Gilroy 8.0
Jul 03, 2026
Lisa Gilroy takes her shoes off to visit with Logan and Dylan (Love on the Spectrum) then stay for her 8th* episode.🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in your…
Dylan & Logan from LOVE ON THE SPECTRUM
Jun 25, 2026
Love on the Spectrum is a masterclass in being in touch with your needs and learning how to communicate them. LOGAN and DYLAN are two of the newest players in seasons 4 (now available on Netflix)…
Kevin Nealon 2.0
Jun 16, 2026
Kevin Nealon (Saturday Night Live, Happy Gilmore, The Larry Sanders Show, Weeds, Hiking with Kevin) takes his shoes off for the second time.🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in…
Alison Brie
Jun 10, 2026
Alison Brie takes her shoes off to talk about He-Man and even other things. Don't believe me? Hahaha, okay.🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in your…
Nick Kroll 2.0
Jun 04, 2026
Nick Kroll (Too Much Tuna, Big Mouth, Kroll Show, Mating Season, Date Night, Sing, The League) takes his shoes off for the second time as he and Rick Glassman talk about stuff. Don't believe me?…
Lamorne Morris
May 28, 2026
Lamorne Morris takes his shoes off for the 7th, and he's no longer a new girl. Now, he's a new boy, on Spider-Noir, opposite Nicholas Cage-- available now on Amazon Prime. 🎟️ Find out when RICKY’S ON…
Matt McCusker (THE SLEEPOVER SERIES)
May 20, 2026
Matt McCusker takes his shoes off for the first time to talk with Rick about Matt and Shane's Secret Podcast (MSSP), basketball, strong girls, and even other stuff. Don't believe me? Hahaha, okay.🎟️…
Bill Lawrence 2.0 (Creator of all the TV shows)
May 12, 2026
Bill Lawrence (or as we like to call him, William Van Duzer Lawrence the 4th) isn't only the guy who gave Rick Glassman his first TV show job on the NBC show Undateable, he is also the creator of…
Bryan Callen 2.0
May 05, 2026
Bryan Callen takes his shoes off to talk with Rick Glassman about stuff.🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in your city:https://www.rickglassman.com/tour📍 Upcoming dates:🗓️ May…
Tan France (Queer Eye)
Apr 28, 2026
Tan France takes his shoes off to talk with Rick about Queer Eye (one of Rick's fav shows), his new podcast, Honorable Gays!, and even other stuff.🎟️ Find out when RICKY’S ON THE LOOSE is doing his…
Jorma Taccone
Apr 22, 2026
Jorma Taccone, of LONLEY ISLAND, takes his shoes off for the first time to talk about stuff. Don’t believe me? Hahaha, okay…Make sure to check out his new movie starring Jason Segel and TYSO alum…
Andrew Santino
Apr 16, 2026
Episode 350 invites Andrew Santino to come take his shoes off for the 4th time. The boys almost choose not to post this episode because Rick's assistant, Duncan, sent cookies and din't warn them that…
Johnny Pemberton
Apr 07, 2026
Johnny Pemberton takes his shoes off for the second time to talk with Rick about his new movie, Mermaid, as well as his show, Fallout (it's AWESOME!).Take Your Shoes Off is nominated for 2 WEBBY…
Mark Normand
Apr 01, 2026
Mark Normand takes his shoes off for the 7th time to talk with Rick. Watch Mark's new Netflix Standup Comedy Special, NONE TOO PLEASED.Take Your Shoes Off is nominated for 2 WEBBY AWARDS! Link to…
Brent Adam (BEST FRIENDS' CLUB)
Mar 25, 2026
The boys are back for another Best Friends' Club. This is Brent Morin & Adam Ray’s 9th appearance together on TYSO.Shout out to James Blake and his new album TRYING TIMES…