Rick Glassman

Take Your Shoes Off w/ Rick Glassman

Comedy EN ↓ 369 episodes

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...

Author

Rick Glassman

Episodes

T.J. Miller 14.01.2026 3:00:21

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 CO...

Paul Rudd 3.0 07.01.2026 2:00:00

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/r...

Ms. Pat 23.12.2025 1:50:44

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 C...

Pete Holmes 3.0 17.12.2025 1:39:02

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...

Nick Kroll 15.12.2025 1:43:41

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...

Sebastian Maniscalco 01.12.2025 1:20:40

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...

Jim Gaffigan (THE SLEEPOVER SERIES) 25.11.2025 2:15:56

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/rickglassma...

Mark Normand and Jon Rudnitsky (THE SLEEPOVER SERIES) 18.11.2025 1:21:48

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, T...

Lisa Gilroy & Ben Schwartz (BEST FRIEND'S CLUB) 12.11.2025 2:14:52

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:...

Sal Vulcano 4.0 05.11.2025 2:23:56

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...

Kristen Bell 3.0 28.10.2025 1:39:38

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 • Clevelan...

Todd Glass 3.0 22.10.2025 2:19:26

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/rickglassm...

Adam Ray & Brent Morin [Best Friend's Club] 14.10.2025 1:43:55

Brent Morin and Adam Ray make their 7th appearance together with Rick on TYSO. 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman 📍 Upcoming dates: 🗓️ October 16–18 • Toronto, ON 🗓️ October 19 • Buffalo, NY 🗓️ 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 C...

Coast Contra 08.10.2025 1:59:20

Coast Contra ( an American hip hop group formed in 2015 by Mario Lozano Mosquera, Eric Jamal Morrison, and twin brothers Taj Austin and Ras Austin) take their shoes off to talk about stuff with Rick. Don't believe us? Then maybe give this a listen. Watch with video here: https://youtu.be/qzhxBn6LfYY 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman 📍 Upcomin...

Craig Conant 30.09.2025 2:27:46

Craig takes his shoes off to talk about stuff with Rick Glassman. Watch video here: https://youtu.be/fIwvlt93zsM 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman 📍 Upcoming dates: 🗓️ October 3 • Atlanta, GA 🗓️ October 4 • Raleigh, NC 🗓️ October 17–18 • Toronto, ON 🗓️ October 19 • Buffalo, NY 🗓️ October 30 • New York, NY 🗓️ November 1 • Brooklyn, NY 🗓️ Decem...

Rhett & Link 23.09.2025 2:03:51

Rhett & Link from (Mythical Pod and Mythical Kitchen) and their wonder holes take their shoes off. 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour : https://www.punchup.live/rickglassman 📍 Upcoming dates: 🗓️ September 26–27 • Detroit, MI 🗓️ October 3 • Atlanta, GA 🗓️ October 4 • Raleigh, NC 🗓️ October 17–18 • Toronto, ON 🗓️ October 19 • Buffalo, NY 🗓️ October 30 • New York, NY 🗓️ November 1 •...

Cristina Mariani 17.09.2025 3:10:07

Cristina Mariani takes her shoes off to talk with Rick. Watch on YouTube: https://youtu.be/dp7lTlHNCWY?si=qA1E4oeZ8LD0pLbB 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman 📍 Upcoming dates: 🗓️ September 26–27 • Detroit, MI 🗓️ October 3 • Atlanta, GA 🗓️ October 4 • Raleigh, NC 🗓️ October 17–18 • Toronto, ON 🗓️ October 19 • Buffalo, NY 🗓️ October 30 • New Yor...

Kevin Nealon 10.09.2025 2:02:06

Kevin Nealon (Saturday Night Live, Happy Gilmore, The Larry Sanders Show, Weeds, Hiking with Kevin ) takes his shoes off and becomes BFFs with Rick Glassman. 👟😂 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour: https://www.punchup.live/rickglassman 📍 Upcoming Dates: 🗓️ September 26–27 • Detroit, MI 🗓️ October 3 • Atlanta, GA 🗓️ October 4 • Raleigh, NC 🗓️ October 17–18 • Toronto, ON 🗓️ October 19...

Ian Fidance 2.0 02.09.2025 1:42:36

The AC is broken and it's HOT. Ian Fidance and Rick Glassman take their shoes AND pants off (to put on shorts). WATCH ON YOUTUBE HERE: https://youtu.be/nUs7QYaZvpw 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman 📍 Upcoming dates: 🗓️ September 4–6 • North Charleston, SC 🗓️ September 26–27 • Detroit, MI 🗓️ October 3 • Atlanta, GA 🗓️ October 4 • Raleigh, NC...

Blaine Anderson - A Professional Dating Coach 27.08.2025 2:26:11

Blaine Anderson is a professional dating coach and match maker. 💘 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman 📍 Upcoming dates: 🗓️ September 4–6 • North Charleston, SC 🗓️ September 26–27 • Detroit, MI 🗓️ October 3 • Atlanta, GA 🗓️ October 4 • Raleigh, NC 🗓️ October 17–18 • Toronto, ON 🗓️ October 19 • Buffalo, NY 🗓️ October 30 • New York, NY 🗓️ Novembe...

Dax Flame 2.0 19.08.2025 1:56:31

Dax Flame takes his shoes off AGAIN and talks with Rick Glassman about stuff. 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour: https://www.punchup.live/rickglassman 📍 Upcoming dates: 🗓️ August 7–9 • Grand Rapids, MI 🗓️ August 14–16 • Dania Beach, FL 🗓️ August 23 • Los Angeles, CA 🗓️ September 4–6 • North Charleston, SC 🗓️ September 26–27 • Detroit, MI 🗓️ October 3 • Atlanta, GA 🗓️ October 4 • Ral...

Veronika Slowikowska: The Sleepover Series in New York 12.08.2025 1:51:31

Veronika Slowikowska, of Tires and the Nevermind Podcast, makes her first TYSO appearance and she and Rick meet for the first time. And let's just say they "podcast," during a sleepover, if you know what I mean. ;) Watch this episode on YouTube here: https://youtu.be/o4nDIWSVQkQ 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman 📍 Upcoming dates: 🗓️ August 7–...

Jerrod Carmichael: The Sleepover Series in New York 05.08.2025 2:38:42

Jerrod Carmichael makes his first TYSO appearance and boy are our arms tired! Check out the follow up to Emmy Award Winning "Rothaniel," his newest stand up special, "Jerrod Carmichael: Don't Be Gay." On HBO here: https://www.hbomax.com/movies/jerrod-carmichael-dont-be-gay/797f6457-02b4-4309-8996-998dcf203d0d 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman...

Lisa Gilroy 5.0 29.07.2025 2:03:31

Lisa takes her shoes off with Rick. Don't believe me? Hahahaha oooooookay... 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman 📍 Upcoming dates: 🗓️ August 7–9 • Grand Rapids, MI 🗓️ August 14–16 • Dania Beach, FL 🗓️ August 23 • Los Angeles, CA 🗓️ September 4–6 • North Charleston, SC 🗓️ September 26–27 • Detroit, MI 🗓️ October 3 • Atlanta, GA 🗓️ October 4 • Ra...

Abbey & David (Love on the Spectrum) 23.07.2025 1:39:44

Love on the Spectrum's Abbey Romeo & David Isaacman take their shoes off. With them are Abbey's mom, Christine and TYSO House Musician, George Krikes. Songs, laughs, and more on this episode of Take Your Shoes Off! Watch on YouTube here: https://youtu.be/x7xFg5bgOhQ 🎟️ Get tickets to the RICKY'S ON THE LOOSE tour at https://www.punchup.live/rickglassman 📍 Upcoming dates: 🗓️ August 7–9 • Grand...