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!
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!
Episodes
Mentioned books
Dec 23, 2025 • 1h 51min
Ms. 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/follow Support 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/storeSupport the show: https://www.patreon.com/takeyourshoesoff
Dec 17, 2025 • 1h 39min
Pete 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/follow 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/storeSupport the show: https://www.patreon.com/takeyourshoesoff
Dec 15, 2025 • 1h 44min
Nick 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/follow Support 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/store NICK KROLL🌐 Website: https://www.nickkroll.com📸 Instagram: https://www.instagram.com/nickkroll Directed by Rick GlassmanEdited by JonMichael PereiraHandheld Cam Operator:Sound Mixing by Christian HoganAnimation by Tom Bateshttps://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).Support the show: https://www.patreon.com/takeyourshoesoff
Dec 1, 2025 • 1h 21min
Sebastian 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/follow Support 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/storeSupport the show: https://www.patreon.com/takeyourshoesoff
Nov 25, 2025 • 2h 16min
Jim 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/follow Support TYSO by supporting our sponsors: 🧵 The Perfect JeanGet 15% off your first order + Free Shipping, Free Returns, Free Exchanges with code TYSO15https://www.theperfectjean.nyc 🌐 SquarespaceStart your free trial at https://www.squarespace.com/TYSOWhen you're ready to launch, use OFFER CODE: TYSO to save 10% on your first purchase 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 JIM GAFFIGAN🌐 Website: https://www.jimgaffigan.com📸 Instagram: https://www.instagram.com/jimgaffiganSupport the show: https://www.patreon.com/takeyourshoesoff
Nov 18, 2025 • 1h 22min
Mark Normand and Jon Rudnitsky (THE SLEEPOVER SERIES)
TYSO favorites Mark Normand (We Might Be Drunk, Kevin Hart, Gay) and Jon Rudnitsky (Jewish) get to know each other on this New York edition of The Sleep Over Series. 🎟️ 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/follow Support 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. 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 JON RUDNITSKY📸 https://www.instagram.com/jonrudnitsky MARK NORMAND🌐 http://marknormandcomedy.com📸 https://www.instagram.com/marknormandSupport the show: https://www.patreon.com/takeyourshoesoff
Nov 12, 2025 • 2h 15min
Lisa Gilroy & Ben Schwartz (BEST FRIEND'S CLUB)
Ben Schwartz and Lisa Gilroy take their shoes off. Don’t believe me? Watch the episode here: https://youtu.be/NCXBIDsdrEM 🎟️ 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🗓️ May 1–2 • Cleveland, OH ✨ MORE CITIES COMING SOON ✨Get notified when I'm coming to your city: https://punchup.live/rickglassman/follow Support TYSO by supporting our sponsors: Download the Underdog Fantasy app today!Sign up with promo code TYSO to score $100 in Bonus Funds or Entries when you play your first $5. This episode is sponsored by BetterHelp — get 10% off your first month:https://www.betterhelp.com 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 BEN SCHWARTZ🌐 https://www.rejectedjokes.com📸 https://www.instagram.com/rejectedjokes🎧 Ben Schwartz TYSO 1.0: https://www.youtube.com/watch?v=O6E_3AJngR8🎧 Ben Schwartz 2.0: https://youtu.be/pjkS4c5ts5Q LISA GILROY🌐 http://www.lisagilroy.com📸 https://www.instagram.com/thelisagilroy Must be 18+ (19+ in Alabama & Nebraska; 19+ in Colorado for some games; 21+ in Arizona, Massachusetts & Virginia) 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 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).Support the show: https://www.patreon.com/takeyourshoesoff
Nov 5, 2025 • 2h 24min
Sal Vulcano 4.0
Sal Vulcano takes his shoes off for the 4th time to talk with Rick about stuff. Watch on YouTube here: https://youtu.be/IVt_toaD-70 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman📍 Upcoming dates:🗓️ October 30 • New York, NY🗓️ November 1 • Brooklyn, NY🗓️ December 12–13 • Las Vegas, NV🗓️ Jan 9–11 • Phoenix, AZ🗓️ May 1–2 • Cleveland, OH ✨ MORE CITIES COMING SOON ✨Get notified when I'm coming to your city: https://punchup.live/rickglassman/follow Support 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/store SAL VULCANO📸 Instagram: https://www.instagram.com/salvulcano🌐 https://salvulcanocomedy.comSupport the show: https://www.patreon.com/takeyourshoesoff
Oct 28, 2025 • 1h 40min
Kristen Bell 3.0
Kristen Bell takes her shoes off to talk Nobody Wants This Season 1 + 2 now on Netflix. Watch this episode on YouTube here: https://youtu.be/MvO2DIq59PM 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman📍 Upcoming dates:🗓️ October 30 • New York, NY🗓️ November 1 • Brooklyn, NY🗓️ December 12–13 • Las Vegas, NV🗓️ Jan 9–11 • Phoenix, AZ🗓️ May 1–2 • Cleveland, OH ✨ MORE CITIES COMING SOON ✨Get notified when I'm coming to your city: https://punchup.live/rickglassman/follow Support TYSO by supporting our sponsors: 👖 F*%k your khakis and get The Perfect Jean 15% off with code TYSO15 at https://theperfectjean.nyc/TYSO15#theperfectjeanpod 💻 Check out https://www.squarespace.com/tyso for a free trial and use OFFER CODE: TYSO to save 10% off your first purchase of a website or domain. 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 KRISTEN BELL📸 Instagram: https://www.instagram.com/kristenanniebell Piano Player: Michael WienMusic Production & Sound Mixing: Matt Day https://www.instagram.com/dattmayySupport the show: https://www.patreon.com/takeyourshoesoff
Oct 22, 2025 • 2h 19min
Todd Glass 3.0
Todd takes his shoes off for the 3rd time. 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman📍 Upcoming dates:🗓️ October 30 • New York, NY🗓️ November 1 • Brooklyn, NY🗓️ December 12–13 • Las Vegas, NV🗓️ Jan 9–11 • Phoenix, AZ🗓️ May 1–2 • Cleveland, OH ✨ MORE CITIES COMING SOON ✨Get notified when I'm coming to your city: https://punchup.live/rickglassman/follow Support TYSO by supporting our sponsors: Download the Underdog Fantasy app* today, sign up with promo code TYSO to score $100 in Bonus Funds or 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/store TODD GLASS🌐 https://www.toddglass.com📸 https://www.instagram.com/thetoddglassshow Directed by: Rick GlassmanHandheld Cam Operator: @mckonecorkeryEdited by: JonMichael PereiraSound Mixing: Matt Day https://www.instagram.com/dattmayyAnimation: @TomBatesYT https://www.instagram.com/tombates.films *Must be 18+ (19+ in Alabama & Nebraska; 19+ in Colorado for some games; 21+ in Arizona, Massachusetts & Virginia) 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 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)Support the show: https://www.patreon.com/takeyourshoesoff
