Take Your Shoes Off w/ Rick Glassman

Take Your Shoes Off w/ 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!

Episodes

July 2, 2025 159 mins

Brent Morin and Amir K take their shoes off and talk about stuff.

Watch this episode on YouTube here: https://youtu.be/HoKoCwThDks


RICKY'S ON THE LOOSE TOUR - New cities are up, and more coming @ https://www.punchup.live/rickglassman. Grand Rapids, MI ● Dania Beach, FL ● Los Angeles, CA ● North Charleston, SC ● Detroit, MI ● Alpharetta, GA ● Raleigh, NC ● Toronto, ON ● Buffalo, NY ● Las Vegas NV


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Kyle Gordon takes his shoes off to talk with Rick Glassman about stuff.

RICKY'S ON THE LOOSE TOUR - New cities are up, and more coming @ https://www.punchup.live/rickglassman. Grand Rapids, MI ● Dania Beach, FL ● Los Angeles, CA ● North Charleston, SC ● Detroit, MI ● Alpharetta, GA ● Raleigh, NC ● Toronto, ON ● Buffalo, NY ● Las Vegas NV 

Support the show: https://www.patreon.com/takeyourshoesoff

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June 17, 2025 113 mins

Tom Arnold take this shoes off to talk with Rick about stuff. Don't believe me? Haha, okay. Watch this episode and tell me I'm wrong. Also, we have a pretty cool supers phone call. ;)

RICKY'S ON THE LOOSE TOUR - New cities are up, and more coming @ https://www.punchup.live/rickglassman. Grand Rapids, MI ● Dania Beach, FL ● Los Angeles, CA ● North Charleston, SC ● Toronto, ON ● Buffalo, NY ● Las Vegas NV 


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June 11, 2025 89 mins

Brett Gelman takes his shoes off for the first time to talk with Rick about stuff.


Support TYSO by supporting our sponsors:

  • This episode is sponsored by Better Help. As the largest online therapy provider in the world, BetterHelp can provide access to mental health professionals with a diverse variety of expertise. Get 10% off you first month at https://www.betterhelp.com/tyso.
  • Factor meals arrive fresh and ready to eat&m...
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June 3, 2025 118 mins

Grace takes her shoes off (and brings donuts) to chat with Rick.

📺 Watch on YouTube: https://youtu.be/YYwSBYwTuWQ
👕 Merch: https://www.rickglassman.com/store
📆 Tour Dates: https://www.punchup.live/rickglassman


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<...

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May 26, 2025 116 mins

Chelsea takes her shoes off for the first time to talk with Rick about stuff.


Support TYSO by supporting our sponsors:

Support the show: https://w...

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Ari Shaffir makes his 5th appearance on TYSO while he and Rick are in New York.


Support TYSO by supporting our sponsors:

  • Make this your best season yet with nutritious, 2-minute meals from Factor. Eating well has never been this easy: just heat up and enjoy, giving you more time to do what you want. Get started at https://www.factormeals.com/TYSO50OFF and use code TYSO50OFF to get 50% off plus FREE shipping on y...
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Paul Rudd and Rick Glassman have a bit of a schedule issue, but all works out. The Sleepover Series New York Edition. Get tickets to Rick’s stand up tour at https://www.punchup.live/rickglassman

🎥 Prefer to watch with video? Check out the full episode on YouTube here: https://youtu.be/3KbSEVTaB2c


 Support TYSO by supporting our sponsors:

• Cornbread Hemp’s CBD gummies are made to help you feel better, wh...

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The Sleep Over Series is back, in New York, with comedian Jordan Jensen (Bein’ Ian with Jordan, RIP podcast) returns for her 5th appearance on Take Your Shoes Off.

🎥 Prefer to watch with video? Check out the full episode on YouTube here: https://youtu.be/lAYS6Rc64FQ


Support TYSO by supporting our sponsors: Goto https://www.helixsleep.com/tyso for 27% Off Sitewide + FREE Bedding Bundle (Sheet Set and Mattress Protec...

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Comedian and actress Melissa Villaseñor (Saturday Night Live, America’s Got Talent, Netflix’s Verified Stand-Up) takes her shoes off and joins Rick for a refreshingly honest episode.

Melissa opens up about feeling embarrassed early in her career, the fear of not being funny, and learning how to trust her real voice — both on stage and in ...

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April 15, 2025 91 mins

Episode 300 for TSYO. Episode 25 for Adam Ray. Episode 9 for Brent Morin. Take your shoes off for our 6th Anniversary of TYSO.

RICKY'S ON THE LOOSE TOUR dates & tickets here: https://www.punchup.live/rickglassman 

Portland, ME • San Jose, CA • Los Angeles, CA, Grand Rapids, MI, Dana Beach, FL, and MORE CITIES COMING SOON - sign up for my e-mail list to be notified when I'm coming to your city here: https://punchu...

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April 8, 2025 109 mins

Harland Williams takes his bakes off for the 6th time to talk with Rick Glassman. Don’t believe me? Give this a watch.


RICKY'S ON THE LOOSE TOUR dates & tickets here: https://www.punchup.live/rickglassman 

Sacramento, CA • Portland, ME • San Jose, CA • Los Angeles, CA and MORE CITIES COMING SOON - sign up for my e-mail list to be notified when I'm coming to your city here: https://punchup.live/ric...

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March 31, 2025 112 mins

The Sleepover Series, New York edition, continues this week with Joe Santagato. Joe hosts the wildly popular podcast, The Basement Yard, along side his co-host, Frank Alvarez. Frank was scheduled to take his shoes off along side Joe, but for reasons that you'll have to listen to in this podcast, he couldn't make it. If you like people talking into microphones, I have a feeling you'll like this episode.


RICKY'S ON THE LOOS...

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Mark Normand (We Might Be Drunk, Tuesdays with Stories) visits Rick in studio to podcast. Don't believe me? Well, you might want to check out this episode to see.


RICKY'S ON THE LOOSE TOUR! My new US stand up tour! Dates & Tickets here: https://www.punchup.live/rickglassman Madison, WI • Sacramento, CA • Portland, ME • San Jose, CA • Los Angeles, CA and MORE CITIES COMING SOON - sign up for my e-mail li...

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The Are You Garbage Boys (Kevin Ryan and H. Foley) take their shoes off for the second time... This time in a New York hotel (last time was in New Jersey. Watch it here: https://www.youtube.com/watch?v=Sm9tUmyOCdA). Check out their Route 66 Tour | Comedy Special (2025) here: https://youtu.be/OSkJS1gCDR4?si=R11L25qGvxo7ai1-


RICKY'S ON THE LOOSE TOUR! My new US stand up tour! Dates & Tickets here: https://www.punchup.live/ri...

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Jay Mohr takes his shoes off then meets Rick's Dad & Cousin Teddy.

RICKY'S ON THE LOOSE TOUR! My new US stand up tour! Dates & Tickets here: https://www.punchup.live/rickglassman

Brookfield, WI • Minneapolis, MN • Madison, WI • Sacramento, CA • Portland, ME • San Jose, CA • Los Angeles, CA and MORE CITIES COMING SOON - sign up for my e-mail list to be notified when I'm coming to your city here:...

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March 5, 2025 199 mins

Casey Abrams (sings the TYSO Theme song) and George Krikes (TYSO house musician) join forces WITH their shoes off for this very musical friend episode. 

PATH is ending homelessness for individuals, families, and communities. They do this by building affordable housing and providing supportive services throughout California. https://epath.org


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  • Experience the m...
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February 26, 2025 161 mins

Grace Kinstler, American Idol top 3 finalist, takes her shoes off for the first time. Rick found Grace's singing on instagram a few weeks ago, then invited her onto TYSO the next time she was in LA. So happens that she was coming to LA to record acoustic videos for her music -- and of course we invited TYSO Music Legend, George Krikes to play and sing with Grace. Lots of great music in this one.


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February 10, 2025 128 mins

Annie Lederman (Anniewood) takes her shoes off for the first time with Rick Glassman as they talk about stuff.

Watch on YouTube here: https://youtu.be/mMTN-ad64yU


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February 3, 2025 122 mins

Dax Flame takes his shoes off and talks with Rick Glassman about stuff. Love on the TYSO Spectrum.

Watch on YouTube here: https://youtu.be/PAWP6-Z9ZvI


Support TYSO by supporting our sponsors:

  • Go to https://www.helixsleep.com/tyso for 20% off sitewide + 2 free dream pillows with mattress purchase.
  • Download the DraftKings Sportsbook app and use code SHOESOFF. New customers to get $200 in bonus bets instantly, when you bet $...
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