Episode Overview

Title: Rick Glassman – Desert Ridge Improv – In Studio
Podcast: Holmberg's Morning Sickness (HMS), 98KUPD
Date: January 9, 2026
Guests: Rick Glassman (comedian/podcaster, Take Your Shoes Off), with hosts John Holmberg, Brady Bogen, Bret Vesely, and Dick Toledo

Main Theme:
A fast-paced and candid interview with comedian Rick Glassman, mixing irreverent humor, personal reflection, life advice, and wild anecdotes. Topics range from Glassman’s tardy sprint into the studio, Cleveland roots, and late-bloomer relationship stories, to cultural quirks, introspection, and his comedy career, all peppered with the show's trademark offbeat banter.

Key Discussion Points & Insights

Rick’s “Hollywood” Arrival

• Running Late:
  • Rick Glassman arrives late, jokingly discussed as a logistical “disaster” given another guest (Marlon Wayans) is also scheduled.

    “He’s got to race up the stairs and then fly into the studio. … That was an impressive pull in; that car was leaning on two wheels, like Speed Buggy.” — John (01:16)

  • Rick explains he set his alarm to LA time (one-hour behind).

    “I set the alarm when I was in LA. … Yeah, dummy.” — Rick (01:49)

• Dog Carrying:
  • Rick notably brings his dog, Alvin, with him, which becomes a running joke.

Cleveland Roots and Sports Fandom

• Not a Sports Guy:
  • Rick is from Cleveland but isn't a Browns/football fan, unlike his family.
  • Shares his grandmother’s intense (and hilarious) Browns fandom—she watches games alone in her closet to manage her anxiety.

    “She watches the games in the closet. … She won’t let watch any games with anybody.” — Rick (03:54)

• Family on The Rich Eisen Show:
  • Rick reveals his grandma is a monthly caller for the Rich Eisen sports show.

    “My grandma’s on the Rich Eisen show once a month … And she calls in. They call her. It’s really cool.” — Rick (03:32)

“Plastic on the Furniture”: Cultural/Ethnic Humor

• Grandparent Stereotypes:
  • The crew humorously debates why grandparents put plastic on furniture, with Rick theorizing about cultural and familial trends.
  • John jokes it's “to keep squirting grandmothers from ruining stuff,” leading to a riotous (and intentionally awkward) digression.

    “That generation’s way of keeping the squirting grandmothers from ruining stuff.” — John (06:10)
    “You’re talking about when grandmas have orgasms… and you think that’s why they put plastic down.” — Rick (06:30)

Rick’s Awkward Journey into Dating & Comedy Material

• Late Bloomer:
  • Rick didn’t have his first kiss until nearly 18 and bought books to learn about kissing—one by Kim Cattrall, which was more about sex than basic kissing.

    “I didn’t have my first kiss until I almost graduated from high school. And I ended up buying a book to learn how to kiss. And the book was about squirting … from Sex and the City I learned that only 14% of women can orgasm penetratively before I ever kissed a woman.” — Rick (07:36)

  • Quotes and stats from the book become comedy fodder.
• Connected Firsts:
  • Rick says his first kiss and first sexual experience were with the same person, and gently sidesteps further detail out of respect for a Phoenix ex and her parents, who might listen.

Comedy, Popular Podcasts, and Upcoming Shows

• Desert Ridge Improv:
  • Rick is headlining all weekend at the Desert Ridge Improv; playfully claims only “a thousand tickets left.”

    “Buy tickets soon because I think we have only a thousand tickets left.” — Rick (11:49)

• Take Your Shoes Off Podcast:
  • Promotes his own podcast, mentioning big upcoming guests.

    “I have Jack Black and Paul Rudd on. I’m really excited about this.” — Rick (13:07)

On Self-Awareness, Questioning, and Social Growth

• Main Life Lesson:
  • Rick shares his core personal growth insight: most people too readily fill in unknowns instead of asking direct questions. He ties this to a story of realizing, in adulthood, that he wasn’t as socially included as he’d thought.

    “I don’t think people know how often they don’t know something. … They fill in the blank with poor critical thinking. … I became aware of how important it is to ask questions.” — Rick (15:20)

  • The catalyst was being gently excluded from a Hollywood basketball game—Bill Lawrence emailed Rick explaining some didn’t enjoy his ultra-competitive style.

    “Turns out guys don’t even WANT to play with me. … I was playing different. In my world the value comes from winning; in their world, it’s about having a good time.” — Rick (17:14)

Basketball & ‘I Am Phenomenal’

• Basketball Obsession:
  • Rick discusses his competitive (and sometimes isolating) intensity in pickup basketball, leading to a short film and music video, "I am Phenomenal," processing being unwittingly “that guy” no one wanted to play with.

    “I was intense; I thought I was the best … You can see on YouTube, it’s called ‘I am Phenomenal.’ Joel McHale plays Bill Lawrence in it.” — Rick (18:09)

Humorous Childhood Anecdotes

• “Bullying” at Basketball Camp:
  • Rick tells a story of gently pranking kids at basketball camp, culminating with a child asking him to sign his shoes after being knocked over by a basketball.

    “I threw this ball at this kid … He goes, ‘Will you sign my shoes?’ … Now I’m here telling you I didn’t have any friends growing up.” — Rick (23:05)

Final Thoughts, Callbacks, and Plugs

• Relationship Reflection:
  • Rick half-jokes about writing a book on getting ex-girlfriends back.
  • Bids farewell, thanking the hosts for still letting him come in despite being late.

    “Glad you still let me come in … Rick Glassman at the Desert Ridge Improv. Desertridgeimprov.com.” — John (23:57)

Memorable Quotes & Moments with Timestamps

• On Arriving Late

  “I set the alarm when I was in LA. … Yeah, dummy.” — Rick (01:49)

• Family Football Fandom

  “She watches the games in the closet. … She won’t let watch any games with anybody.” — Rick (03:54)

• On Plastic Couch Covers & Squirting Grandmothers

  “That generation’s way of keeping the squirting grandmothers from ruining stuff.” — John (06:10)

• On Self-Education

  “I didn’t have my first kiss until I almost graduated from high school. … I bought this book from Kim Cattrall and it was all about the clitoris.” — Rick (07:36)

• On Self-Awareness and Social Growth

  “I became aware of how important it is to ask questions. Answers are relatively easy if you have the curiosity to ask.” — Rick (16:01)

• On Pick-Up Basketball

  “Turns out guys don’t even WANT to play with me ... In my world, the value comes from winning … In their world, it comes from getting away from the family and having a nice time.” — Rick (17:14)

• Basketball Camp Revelation

  “I threw this ball at this kid … He goes, ‘Will you sign my shoes?’” — Rick (23:05)

Noteworthy Segments & Timestamps

• [01:16] Rick’s frantic entry into the studio
• [03:32] Discussion about Rick’s grandmother on The Rich Eisen Show
• [06:10–07:03] “Plastic on the furniture” and generational/sexual humor
• [07:36–08:49] Rick’s relationship history, first kiss, and early sexual education
• [15:20–18:55] Rick’s life philosophy about asking questions, and learning from a painful Hollywood social experience
• [18:55–21:00] Pickup basketball and invention of solo games; "I Am Phenomenal" video
• [22:03–23:23] The basketball camp prank and sweet childhood story

Tone and Style

The episode blends observational, irreverent humor (in true HMS fashion) with moments of intimacy and self-deprecation from Rick Glassman. The hosts riff freely, often making intentionally awkward or risqué jokes, but Rick matches with quick wit and candid vulnerability. At times, the conversation is absurdly funny; at others, unexpectedly insightful.

Useful for Listeners

• If you enjoy: Quick-fire comedy, behind-the-curtain looks at comedians’ lives, and honest reflections on friendship, family, and career mishaps, you’ll find this episode both hilarious and refreshingly real.
• If you missed it: You’ll catch all the big stories—Rick’s wild arrival, Cleveland family quirks, his “late-bloomer” adolescence, his journey toward self-awareness, plus inside-baseball tales of comedy, basketball, and podcasting.