Big Jay Oakerson

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. S...

26 Feb 20252h 41min

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 spons...

11 Feb 20252h 8min

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 ...

4 Feb 20252h 2min

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...

28 Jan 20251h 53min

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.....

24 Jan 20251h 57min

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/VjM9Rcrvrv...

14 Jan 20251h 26min

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 ...

7 Jan 20252h 44min

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! Date...

24 Des 20241h 15min