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

April 22, 2025 112 mins

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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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


Support TYSO by supporting our sponsors:

  • 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.


Support TYSO by supporting our ...

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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


Support TYSO by supporting out sponsors:

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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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Rick performed at The Helium Comedy Club in Portland then stayed a few extra days, where he met Kyle Kinane who was performing at the same club. Don't believe me? Check this ep out. Watch this episode on YouTube here: https://youtu.be/Z9Jb407y9ag


Support TYSO by supporting out sponsors:

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Jon Rudnitsky (SNL, Curb Your Enthusiasm) makes his 5th appearance on TYSO -- this time live in LA, in front of 100,000* people. A surprise TYSO favorite(s) may or may not make an appearance as well...


Support TYSO by supporting our sponsors:

  • If you were wondering what drink Rick takes before most podcasts, it's called MAGIC MIND. Focus and Sleep shots, bundled up for the first time, at a 45% off, exclusive at https:...
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January 14, 2025 86 mins

Ari Shaffir takes his shoes off for the 4th time to talk about his new Netflix special America’s Sweetheart out now, and yada yada yada. Watch this episode on YouTube here: https://youtu.be/VjM9Rcrvrvg


Support TYSO by supporting our sponsors:

  • Stop putting off those doctors appointments and go to https://www.zocdoc.com/tyso to find and instantly book a top-rated doctor today.

  • ...

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January 7, 2025 164 mins

Sona Movsesian (Conan O'Brien Needs a Friend podcast, "World's Worst Assistant") is one of Rick's dear friends, and we welcome her back for her traditional annual January episode. She takes her shoes off for the 6th as Rick Needs a Friend. This is a more vulnerable episode for Rick than the traditional TYSO. He almost... "He"... Hi, I'm Rick, and I'm writing this description.

This is one of the few episodes I've recorded that I alm...

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December 23, 2024 75 mins

Santa Clause comes down the TYSO chimney with his shoes off for another round of talking and stuff. 

Merch @ https://www.rickglassman.com/store


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

Los Angeles, CA • San Diego, CA • Phoenix, AZ • Eugene, OR • Portland, OR • Denver, CO • West Jordan, UT • Boston, MA • P...

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December 17, 2024 142 mins

Harland Williams, Harland Highway, blah blah blah.

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

Los Angeles, CA • San Diego, CA • Phoenix, AZ • Eugene, OR • Portland, OR • Denver, CO • West Jordan, UT • Boston, MA • Philadelphia, PA • Brookfield, WI • Minneapolis, MN • Madison, WI • Sacramento, CA •...

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December 10, 2024 134 mins

Ashley Christine (Modern Day Eratosthenes) is a STEM (science, technology, engineering and mathematics) content creator that Rick discovered a couple years ago. Her content is so interesting, Rick invited her to take her shoes off to talk all things science, space, and nerd.

Follow her here:

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December 2, 2024 114 mins

The Best Friend's Club is back! Brent Morin and Adam Ray come over and get silly with Rick Glassman. Don't believe me?! Give it a listen.

RICK'S ON THE LOOSE TOUR! My new US stand up tour! Dates & Tickets here: https://www.punchup.live/rickglassman JJanuary 8th San Diego, CA • January 9th Phoenix, AZ • January 15th Eugene, OR • January 16th Portland, OR • February 12th Denver, CO • February 13th West Jo...

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November 25, 2024 173 mins

If you like a BEAUTIFUL voice and SOUL in your singers, then you already/will love Allen Stone. He takes his shoes off and plugs his guitar in as he and Rick talk about stuff. Fan favorite, George Krikes, comes back over with his guitar and pipes as he and Allen meet for the first time. Listen to them sing and play together and you may have a hard time believing that they never met. LOTS of music in this episode. Watch it on YouTub...

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