Take Your Shoes Off w/ Rick Glassman
Rick Glassman
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!
- 1 hour 53 minutesFiona Cauley
Fiano takes her shoes off and talks with Rick about stand up, Kill Tony, how she and her husband Matt Taylor met, and even other stuff. Don't believe us? Haha, okay. Why don't you listen to this episode and see for yourself.
🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in your city!
https://www.rickglassman.com/tour📍 Upcoming dates:
🗓️ February 7 • San Francisco, CA
🗓️ February 26–28 • Denver, CO
🗓️ March 26–29 • Houston, TX
🗓️ April 23–25 • Austin, TX
🗓️ May 1–2 • Cleveland, OH
🗓️ May 7–9 • Irving, TX✨ MORE CITIES COMING SOON ✨
Get notified when Rick is coming to your city:
https://www.punchup.live/rickglassman/followSupport TYSO by supporting our sponsors:
- Head to https://www.factormeals.com/tyso50off and use code tyso50off to get 50% off your first Factor box PLUS free breakfast for 1 year.
- This episode is sponsored by Betterhelp. Sign up and get 10% off at https://www.betterhelp.com/tyso.
- Download the Underdog Fantasy app and use promo code TYSO to score $75 in Fantasy Bonus Entries when you play your first$5 on Fantasy.*
RICK GLASSMAN
📸 Instagram: https://www.instagram.com/rickglassman
🎬 TikTok: https://www.tiktok.com/@rickglassman
🎙️ Patreon: https://www.patreon.com/takeyourshoesoff
💬 Discord: https://discord.gg/Z2v4HTC
🎟️ Tour Dates: https://www.punchup.live/rickglassman
🃏 TYSO Cards: https://www.tysocards.com
🛍️ Store: https://www.rickglassman.com/storeFIONA CAULEY
📸 Instagram: https://www.instagram.com/fionacauley
🌐 Website: https://www.fionacauley.com* Must be 18+ (19+ in AL, NE; 19+ in CO for some games; 21+ in AZ, MA, and VA) and present in a state where Underdog Fantasy operates. Terms apply. See assets.underdogfantasy.com/web/PlayandGetTerms_DFS_.html for details. Offer not valid in MD, MI, NJ, NY, OH, and PA. Concerned with your play? Call 1-800-GAMBLER or visit www.ncpgambling.org; NY: Call the 24/7 HOPEline at 1-877-8-HOPENY or Text HOPENY (467369).
4 February 2026, 8:31 pm - 2 hours 52 minutesSona Movsesian 7.0
Sona takes her shoes off for the 7th time and talks with Rick about stuff.
🎟️ Find out when RICKY’S ON THE LOOSE is doing his hour in your city!
https://www.rickglassman.com/tour📍 Upcoming dates:
🗓️ February 7 • San Francisco, CA
🗓️ February 26–28 • Denver, CO
🗓️ March 26–29 • Houston, TX
🗓️ April 23–25 • Austin, TX
🗓️ May 1–2 • Cleveland, OH
🗓️ May 7–9 • Irving, TX✨ MORE CITIES COMING SOON ✨
Get notified when Rick is coming to your city:
https://www.punchup.live/rickglassman/followSupport TYSO by supporting our sponsors:
- Right now, Momentous is offering our listeners up to 35% off your first order with promo code TYSO. Head to https://www.livemomentous.com, and use promo code TYSO for up to 35% off your first order
- Their meal delivery service is SO good. Goto https://www.gomethodology.com/tyso to get 10% off your first order.
28 January 2026, 8:41 pm - 1 hour 25 minutesHarland Williams 7.0
Harland Williams takes his shoes off for the 7th time as he and Rick Glassman talk about stuff.
🎟️ Find out when RICKY'S ON THE LOOSE is in your city!
https://www.rickglassman.com/tour📍 Upcoming dates:
🗓️ January 23–24 • Pittsburgh, PA
🗓️ February 7 • San Francisco, CA
🗓️ February 26–28 • Denver, CO
🗓️ March 26–29 • Houston, TX
🗓️ May 1–2 • Cleveland, OH
🗓️ May 7–9 • Irving, TX✨ MORE CITIES COMING SOON ✨
Get notified when Rick is coming to your city:
https://www.punchup.live/rickglassman/followSupport TYSO by supporting our sponsors:
- Sign up for your $1 per-month trial and start selling today at https://www.shopify.com/tyso
- Download the Underdog Fantasy app today and use promo code TYSO to get $75 in Bonus Entries when you play your first $5. Terms and conditions apply*.
RICK GLASSMAN
📸 Instagram: https://www.instagram.com/rickglassman
🎬 TikTok: https://www.tiktok.com/@rickglassman
🎙️ Patreon: https://www.patreon.com/takeyourshoesoff
💬 Discord: https://discord.gg/Z2v4HTC
🎟️ Tour Dates: https://www.punchup.live/rickglassman
🃏 TYSO Cards: https://www.tysocards.com
🛍️ Store: https://www.rickglassman.com/store🎤 Harland Williams
📸 Instagram: https://www.instagram.com/harlandwilliams 😎
🌐 Website: https://www.harlandwilliams.com 🎬*Must be 18+ (19+ in AL, NE; 19+ in CO for some games; 21+ in AZ, MA, and VA) and present in a state where Underdog Fantasy operates. Terms apply. See assets.underdogfantasy.com/web/PlayandGetTerms_DFS_.html for details. Offer not valid in MD, MI, NJ, NY, OH, and PA. Concerned with your play? Call 1-800-GAMBLER or visit www.ncpgambling.org; NY: Call the 24/7 HOPEline at 1-877-8-HOPENY or Text HOPENY (467369).
20 January 2026, 8:34 am - 3 hours 22 secondsT.J. Miller
TJ Miller takes his pants off. Don't believe? Why don't you give this a listen then.
🎟️ Find out when RICKY'S ON THE LOOSE is in your city!
https://www.punchup.live/rickglassman/follow📍 Upcoming dates:
🗓️ January 23–24 • Pittsburgh, PA
🗓️ February 7 • San Francisco, CA
🗓️ February 26–28 • Denver, CO
🗓️ March 26–29 • Houston, TX
🗓️ May 1–2 • Cleveland, OH
🗓️ May 7–9 • Irving, TX✨ MORE CITIES COMING SOON ✨
Get notified when Rick is coming to your city:
https://www.punchup.live/rickglassman/followSupport TYSO by supporting our sponsors:
- AG1 has over 50,000 verified 5-star reviews and comes with a 90-day money-back guarantee. Go to https://www.drinkag1.com/tyso and for a limited time, get a FREE AG1 duffel bag and FREE AG1 Welcome Kit with your first subscription order!
- Go to https://www.helixsleep.com/tyso now for 20% Off Sitewide. Make sure you enter our show name after checkout so they know we sent you!
- Download the Underdog Fantasy app today and use promo code TYSO to score $75 in Bonus Entries when you play your first $5. Terms* apply. See site for details.
RICK GLASSMAN
📸 Instagram: https://www.instagram.com/rickglassman
🎬 TikTok: https://www.tiktok.com/@rickglassman
🎙️ Patreon: https://www.patreon.com/takeyourshoesoff
💬 Discord: https://discord.gg/Z2v4HTC
🎟️ Tour Dates: https://www.punchup.live/rickglassman
🃏 TYSO Cards: https://www.tysocards.com
🛍️ Store: https://www.rickglassman.com/store*Must be 18+ (19+ in AL, NE; 19+ in CO for some games; 21+ in AZ, MA, and VA) and present in a state where Underdog Fantasy operates. Terms apply. See assets.underdogfantasy.com/web/PlayandGetTerms_DFS_.html for details. Offer not valid in MD, MI, NJ, NY, OH, and PA. Concerned with your play? Call 1-800-GAMBLER or visit www.ncpgambling.org; NY: Call the 24/7 HOPEline at 1-877-8-HOPENY or Text HOPENY (467369).
14 January 2026, 6:45 am - 2 hoursPaul Rudd 3.0
Paul Rudd honors his commitments and takes his shoes off with Rick Glassman. The two discuss the accident that happened on their first meeting. They also discuss Paul's large weiner and how he discovered he had a bigger one than most. Watch this on YouTube here: https://www.youtube.com/watch?v=I4rywfHqRTM&t=5943s
🎟️ Find out when RICKY'S ON THE LOOSE is in your city!
https://www.punchup.live/rickglassman/follow📍 Upcoming dates:
🗓️ January 9–11 • Phoenix, AZ
🗓️ January 23–24 • Pittsburgh, PA
🗓️ February 7 • San Francisco, CA
🗓️ February 26–28 • Denver, CO
🗓️ March 26–29 • Houston, TX
🗓️ May 1–2 • Cleveland, OH
🗓️ May 7–9 • Irving, TX✨ MORE CITIES COMING SOON ✨
Get notified when Rick is coming to your city:
https://www.punchup.live/rickglassman/followSupport TYSO by supporting our sponsors:
- This episode is sponsored by BetterHelp. Sign up and get 10% off at https://www.betterhelp.com/tyso
- Head to https://www.factormeals.com/tyso50off and use code TYSO50OFF to get 50% off your first Factor box PLUS free breakfast for 1 year.
RICK GLASSMAN
📸 Instagram: https://www.instagram.com/rickglassman
🎬 TikTok: https://www.tiktok.com/@rickglassman
🎙️ Patreon: https://www.patreon.com/takeyourshoesoff
💬 Discord: https://discord.gg/Z2v4HTC
🎟️ Tour Dates: https://www.punchup.live/rickglassman
🃏 TYSO Cards: https://www.tysocards.com
🛍️ Store: https://www.rickglassman.com/store7 January 2026, 6:48 am - 2 minutes 54 secondsPaul Rudd & Jack Black call Glassman out
This is a 3 minute teaser of next week's episode with Paul Rudd. Rick sneaks into the ANACONDA press junket with his assistant, Duncan.
Watch the video here: https://youtu.be/uQybNe-CFU8
1 January 2026, 7:51 pm - 1 hour 50 minutesMs. Pat
Ms. Pat takes her shoes off.
🎟️ Find out when RICKY'S ON THE LOOSE is in your city!
https://www.punchup.live/rickglassman/follow📍 Upcoming dates:
🗓️ December 12–13 • Las Vegas, NV
🗓️ January 9–11 • Phoenix, AZ
🗓️ January 23–24 • Pittsburgh, PA
🗓️ February 7 • San Francisco, CA
🗓️ February 26–28 • Denver, CO
🗓️ March 26–29 • Houston, TX
🗓️ May 1–2 • Cleveland, OH
🗓️ May 7–9 • Irving, TX✨ MORE CITIES COMING SOON ✨
Get notified when I'm coming to your city:
https://www.punchup.live/rickglassman/followSupport TYSO by supporting our sponsors:
- Check out https://www.squarespace.com/TYSO for a free trial, and when you’re ready to launch, use OFFER CODE: TYSO to save 10% off your first purchase of a website or domain.
- For a limited time, our listeners get 15% off their first order plus free shipping at https://www.theperfectjean.nyc, or Google The Perfect Jean and use code TYSO15 for 15% off.
RICK GLASSMAN
📸 Instagram: https://www.instagram.com/rickglassman
🎬 TikTok: https://www.tiktok.com/@rickglassman
🎙️ Patreon: https://www.patreon.com/takeyourshoesoff
💬 Discord: https://discord.gg/Z2v4HTC
🎟️ Tour Dates: https://www.punchup.live/rickglassman
🃏 TYSO Cards: https://www.tysocards.com
🛍️ Store: https://www.rickglassman.com/store23 December 2025, 6:48 am - 1 hour 39 minutesPete Holmes 3.0
Pete takes his shoes off for the 3rd time.
🎟️ Find out when RICKY'S ON THE LOOSE is in your city!
https://www.punchup.live/rickglassman/follow📍 Upcoming dates:
🗓️ December 12–13 • Las Vegas, NV
🗓️ January 9–11 • Phoenix, AZ
🗓️ January 23–24 • Pittsburgh, PA
🗓️ February 7 • San Francisco, CA
🗓️ February 26–28 • Denver, CO
🗓️ March 26–29 • Houston, TX
🗓️ May 1–2 • Cleveland, OH
🗓️ May 7–9 • Irving, TX✨ MORE CITIES COMING SOON ✨
Get notified when I'm coming to your city:
https://www.punchup.live/rickglassman/followRICK GLASSMAN
📸 Instagram: https://www.instagram.com/rickglassman
🎬 TikTok: https://www.tiktok.com/@rickglassman
🎙️ Patreon: https://www.patreon.com/takeyourshoesoff
💬 Discord: https://discord.gg/Z2v4HTC
🎟️ Tour Dates: https://www.punchup.live/rickglassman
🃏 TYSO Cards: https://www.tysocards.com
🛍️ Store: https://www.rickglassman.com/store17 December 2025, 5:00 pm - 1 hour 43 minutesNick Kroll
Nick Kroll takes his shoes off for the first time.
🎟️ Find out when RICKY'S ON THE LOOSE is in your city!
https://www.punchup.live/rickglassman/follow📍 Upcoming dates:
🗓️ December 12–13 • Las Vegas, NV
🗓️ January 9–11 • Phoenix, AZ
🗓️ January 23–24 • Pittsburgh, PA
🗓️ February 7 • San Francisco, CA
🗓️ February 26–28 • Denver, CO
🗓️ March 26–29 • Houston, TX
🗓️ May 1–2 • Cleveland, OH
🗓️ May 7–9 • Irving, TX✨ MORE CITIES COMING SOON ✨
Get notified when I'm coming to your city:
https://www.punchup.live/rickglassman/followSupport TYSO by supporting our sponsors:
• Check out squarespace.com/TYSO for a free trial, and when you’re ready to launch, use OFFER CODE: TYSO to save 10% off your first purchase of a website or domain.
• Download the Underdog Fantasy app today and use promo code TYSO to score $75 in Bonus Entries when you play your first $5*
RICK GLASSMAN
📸 Instagram: https://www.instagram.com/rickglassman
🎬 TikTok: https://www.tiktok.com/@rickglassman
🎙️ Patreon: https://www.patreon.com/takeyourshoesoff
💬 Discord: https://discord.gg/Z2v4HTC
🎟️ Tour Dates: https://www.punchup.live/rickglassman
🃏 TYSO Cards: https://www.tysocards.com
🛍️ Store: https://www.rickglassman.com/storeNICK KROLL
🌐 Website: https://www.nickkroll.com
📸 Instagram: https://www.instagram.com/nickkrollDirected by Rick Glassman
Edited by JonMichael Pereira
Handheld Cam Operator:
Sound Mixing by Christian Hogan
Animation by Tom Bates
https://www.instagram.com/tombates.film*Must be 18+ (19+ in Alabama & Nebraska; 19+ in Colorado for some games; 21+ in Arizona, Massachusetts, and Virginia) and present in a state where Underdog Fantasy operates. Terms apply. Offer not valid in Maryland, Michigan, New Jersey, New York, Ohio, and Pennsylvania. Concerned with your play? Call 1-800-GAMBLER or visit www.ncpgambling.org. In New York, call the 24/7 HOPEline at 1-877-8-HOPENY or text HOPENY (467369).
15 December 2025, 11:26 pm - 1 hour 20 minutesSebastian Maniscalco
Sebastian Maniscalco takes his shoes off for the first time to talk with Rick. Watch Sebastian Maniscalco: It Ain't Right on Hulu.
🎟️ Find out when RICKY'S ON THE LOOSE is in your city!
https://www.punchup.live/rickglassman/follow📍 Upcoming dates:
🗓️ December 12–13 • Las Vegas, NV
🗓️ January 9–11 • Phoenix, AZ
🗓️ January 23–24 • Pittsburgh, PA
🗓️ February 7 • San Francisco, CA
🗓️ February 26–28 • Denver, CO
🗓️ March 26–29 • Houston, TX
🗓️ May 1–2 • Cleveland, OH
🗓️ May 7–9 • Irving, TX✨ MORE CITIES COMING SOON ✨
Get notified when I'm coming to your city: https://punchup.live/rickglassman/followSupport TYSO by supporting our sponsors:
- Go to https://www.helixsleep.com/tyso now for 20% Off Sitewide. Make sure you enter our show name after checkout so they know we sent you!
RICK GLASSMAN
📸 Instagram: https://www.instagram.com/rickglassman
🎬 TikTok: https://www.tiktok.com/@rickglassman
🎙️ Patreon: https://www.patreon.com/takeyourshoesoff
💬 Discord: https://discord.gg/Z2v4HTC
🎟️ Tour Dates: https://www.punchup.live/rickglassman
🃏 TYSO Cards: https://www.tysocards.com
🛍️ Store: https://www.rickglassman.com/store1 December 2025, 5:00 am - 2 hours 15 minutesJim Gaffigan (THE SLEEPOVER SERIES)
Jim Gaffigan talks with Rick about stuff as they get to know each other on this New York edition of The Sleep Over Series. Watch on YouTube here: https://youtu.be/rttK5Ae0zJk
🎤 Watch his new special Jim Gaffigan: Live from Old Forester — The Bourbon Set: https://www.youtube.com/watch?v=pHzyxWkHWKM&t
🎟️ Find out when RICKY'S ON THE LOOSE is in your city!
https://www.punchup.live/rickglassman/follow📍 Upcoming dates:
🗓️ December 12–13 • Las Vegas, NV
🗓️ Jan 9–11 • Phoenix, AZ
🗓️ Feb 7 • San Francisco, CA
🗓️ Mar 26–29 • Houston, TX
🗓️ May 1–2 • Cleveland, OH
🗓️ May 7–9 • Irving, TX✨ MORE CITIES COMING SOON ✨
Get notified when I'm coming to your city: https://punchup.live/rickglassman/followSupport TYSO by supporting our sponsors:
🧵 The Perfect Jean
Get 15% off your first order + Free Shipping, Free Returns, Free Exchanges with code TYSO15
https://www.theperfectjean.nyc🌐 Squarespace
Start your free trial at https://www.squarespace.com/TYSO
When you're ready to launch, use OFFER CODE: TYSO to save 10% on your first purchaseRICK GLASSMAN
📸 Instagram: https://www.instagram.com/rickglassman
🎬 TikTok: https://www.tiktok.com/@rickglassman
🎙️ Patreon: https://www.patreon.com/takeyourshoesoff
💬 Discord: https://discord.gg/Z2v4HTC
🎟️ Tour Dates: https://www.punchup.live/rickglassman
🃏 TYSO Cards: https://www.tysocards.com
🛍️ Store: https://www.rickglassman.com/storeJIM GAFFIGAN
🌐 Website: https://www.jimgaffigan.com
📸 Instagram: https://www.instagram.com/jimgaffigan25 November 2025, 9:34 pm - More Episodes? Get the App