The BOB & TOM Show – September 1, 2025

Overview

This Labor Day episode of The BOB & TOM Show offers listeners a typical blend of offbeat news stories, irreverent comedy, listener letters, live musical performances, and appearances from favorite guest comedians. The show is packed with the team’s trademark banter, running gags, and light-hearted debates about everything from bodily mishaps to snack etiquette—delivering a holiday broadcast that’s both unpredictable and comfortingly familiar.

Key Discussion Points & Segments

1. Labor Day Musical Opener (00:00–04:20)

• Tom opens the show by lamenting the lack of a Labor Day song and debuts his own, featuring references to union labor, licensing, and tongue-in-cheek holiday customs.
• Deeply satirical lyrics riff on American labor traditions and holidays with lines like “On Labor Day all of the kids go on a Jimmy Hoffa hunt.”

Quote:
"Once they found Amelia Earhart out there... It wasn't Jimmy, so they left her."
– Tom (02:31)

2. Ping Pong Ball Paramedic Story (07:30–17:00)

• The crew dives into a news story about a paramedic in Italy fired after attempting to remove a ping pong ball from a woman’s vagina.
• Panel speculation runs wild: was it a failed stripper stunt, or a beer pong mishap? Much laughter about bizarre medical situations and creative retrieval methods.

Quote:
"I'd love to talk to any physicians out there... When you went to medical school, did you walk into class and the teacher said, ‘Alright, today we’re gonna learn how to get a ping pong ball out of a woman’s vagina!’"
– Tom (12:48)

3. Breastfeeding & "Leaky Mama" Cookies (17:00–22:00)

• Discussion about a cookie shop in Kentucky called “Leaky Mama,” which makes lactation cookies for breastfeeding mothers (but without actual breast milk).
• Christy Lee details the challenges of breastfeeding, sparking personal anecdotes from the cast.

Quote:
"Your milk may or may not come in. You have to feed every two hours. People have gotten better about that, though. Pumping is just... you gotta pump all the time.”
– Christy Lee (19:37)

4. Astronauts Having Sex in Space (23:00–26:40)

• The cast riff on expert speculation about astronauts having sex in zero gravity. Jokes abound about astronaut appearances, potential romantic couplings, and the challenges of space love.

Quote:
"I'd rather sleep with a can opener. He looks like grown up Chunk from the Goonies, right?"
– Tom (25:17)

5. Guest: Henry Phillips Performs Live (29:00–48:30)

• Singer-songwriter-comedian Henry Phillips shares stories about his in-laws, his cooking channel (Henry’s Kitchen) and performs “Things in My Car/Apartment/Room”—a comedic song about personal clutter.
• He discusses situational depression with the crew and shares a classic "wrong Starbucks" mishap story.

Notable Segment:
Song Lyrics (42:15):
"These are the things in my apartment… a little compartment with a silk undergarment, and pills for penile enlargement, and a letter from the police department…”
– Henry Phillips (singing, 43:40)

6. Nightmares & Mortality (48:35–54:44)

• Discussion of a study suggesting frequent nightmares may triple the risk of early death. The cast share dream experiences, including “pee dreams” and bedwetting confessions.

Quote:
"So not only are you not getting laid, but you’re also dying young. Thanks. This is great.”
– Henry Phillips (52:59)

7. Guest: Tommy Brennan & Eel Story (61:20–73:30)

• Comedian Tommy Brennan joins for a segment featuring:
  • A news story about a man hospitalized after a live eel inserted rectally escapes into his abdominal cavity—followed by the unexpected discovery of a lemon.
  • Discussion of Tommy's upbringing in a large family, home surgery stories, and an Iowa stand-up mishap involving local racial contexts.

Quote:
"I’m not gonna judge a man who puts an eel in his anus. Amore is amore, baby.”
– Josh Arnold (67:20)

8. Jamie Lisso: Life Updates & Comedy Process (80:10–102:20)

• Interview with Jamie Lisso, who details splitting his time between Alaska, Boise, and NYC for comedy and family.
• Jokes about the “outkicked your coverage” compliment, how Jamie met his new wife (at a Rob Schneider show), and how radio mornings affect a comic’s day.

Quote:
"Look, after looking at my tax return, she’s decided to continue to work full-time!”
– Jamie Lisso (84:45)

9. Sexy Time with Ally Breen (110:15–127:55)

• Advice segment featuring Ally Breen, with questions ranging from spouses’ overuse of cosmetic enhancement to in-restaurant flirtation, and first date tipping etiquette.
• The crew debates communication about cosmetic surgery (“Lauren Sanchez face” as the example), and the delicate art of offering feedback.

Quote:
"You're starting to not look like you.”
– Christy Lee, suggestion on what to tell a partner about too much filler (115:03)

10. Josh Microwaves His Socks / Yiddish Phrases (130:40–137:53)

• Josh Arnold chronicles microwaving his wet socks after a rainstorm and the possibility of picking up foreign Yiddish phrases for bathroom mishaps.
• Banter about brotherly pranks, the origins of “plots,” and Tom’s family’s swimming naked on vacation.

Quote:
"I'll just throw them in the microwave for two minutes. No, that’s disgusting."
– Josh and Tom (131:35)

11. Cowboy Hats & Cultural Appropriation Debate (145:10–157:30)

• Al Jackson appears via video, kicking off a deep dive on Tom’s potential new cowboy hat (upon dermatologist recommendation due to sun exposure).
• Concerns about pulling off the look, plus a tangent into sombreros and their cultural connotations.

Quote: "If you get one, just have the confidence from within. You’d feel weird for a week, but then you’d just put it on and not think about it.”
– Al Jackson (154:59)

12. Listener Letters: Candy Bars, Breast Milk, and Bosoms (160:00–170:20)

• Letters about oldies songs referencing “sugar,” playful discussions about preferred nicknames for breasts, and why “bosoms” feels so Shakespearean.
• Audience engagement on breast milk in baked goods and bodybuilder diets.

Quote:
"You know that top really highlights your milkers.”
– Tom (165:13)

13. Guest: Derek Stroop on Cologne and Not Driving (172:30–181:47)

• Derek Stroop recounts his enduring love for cologne, even after a strong warning about studio sensitivities.
• Derek shares the story of quitting drinking (and driving) after two DUIs, and how not driving shaped his comedy touring lifestyle.

Quote:
"I’ve heard a lot of DUI stories. They never end this way. They all end with, ‘I have not drank in 14 years.’ You just said you haven’t drove in 14 years!”
– Bert Kreischer (story by Derek Stroop, 179:50)

14. Snacking in Stores and Minor Life Annoyances (183:10–190:42)

• Debating the ethics of eating groceries before paying—rotisserie chickens, grapes, and Pringles.
• Discussion on everyday annoyances: running into people you don’t want to see, loud chewing, and annoying Wi-Fi.

Quote:
"I finished one of those (rotisserie chickens) in the car.”
– Josh (184:09)

15. Show Wrap & Final Guest: Joe Dombrowski on IVF and Gay Parenting (193:37–208:47)

• Joe Dombrowski tells stories of preparing for IVF as a gay couple, jokes about “swirling” semen samples, and discussing gay love language: “Being insulting is a gay love language.”
• Banter about comedy movies and recommended favorites (“The Comedian” documentary about Jerry Seinfeld).

Quote:
"If you don't have anything nice to say, come sit by me."
– Joe Dombrowski (204:09)

Notable Quotes & Memorable Moments

• On Labor Day festivities:
  “On Labor Day, all the kids go on a Jimmy Hoffa hunt.” (Tom, 02:45)
• On medical oddities:
  “How do you get a ping pong ball out? Shop vac.” (Cast, 14:19)
• On breast milk cookies:
  “There’s no breast milk in the cookies. Oh. All right.” (19:05)
• On space sex:
  “I’d rather sleep with a can opener.” (Tom, 25:18)
• On cologne:
  “I put on cologne for all situations…if I’m going to cut grass, your boy's gonna smell good.” (Derek Stroop, 173:10)
• On tipping etiquette:
  “You offered. He’s just trying to do the keep-your-mouth-shut-if-you-don’t-want-mind-games. The first date.” (Josh, 126:09)
• On not driving anymore:
  “I didn’t give up drinking. I gave up the car.” (Derek Stroop, 179:32)

Flow & Tone

The hosts maintain their signature irreverent, rapid-fire tone, weaving in mature humor, “did they really say that?” moments, and self-deprecating wit throughout. Banter is naturally paced, with recurring callbacks to ongoing jokes, and the rapport between veteran hosts and guest comedians is as lively as ever. Sex, bodily functions, family life, and odd news stories are recurring targets for the show’s distinctive brand of comedic discourse.

Timestamps by Topic

• Labor Day Song: 00:00–04:20
• Italian Paramedic / Ping Pong Ball: 07:30–17:00
• Leaky Mama Cookie Shop: 17:00–22:00
• Astronaut Sex Jokes: 23:00–26:40
• Henry Phillips Performance: 29:00–48:30
• Nightmares & Mortality: 48:35–54:44
• Tommy Brennan/Eel Story: 61:20–73:30
• Jamie Lisso Interview: 80:10–102:20
• Ally Breen Sexy Time Letters: 110:15–127:55
• Josh’s Wet Socks / Yiddish: 130:40–137:53
• Al Jackson, Cowboy Hat Debate: 145:10–157:30
• Listener Letters—Candy, Breasts, Bosoms: 160:00–170:20
• Derek Stroop, Cologne, Not Driving: 172:30–181:47
• Snacking Ethics / Annoyances: 183:10–190:42
• Joe Dombrowski on Parenthood: 193:37–208:47

Final Thoughts

This episode of The BOB & TOM Show delivers on its promise of holiday weirdness: from live comedy and musical segments to jaw-dropping news stories and relatable discussions of life’s petty annoyances. For those who missed it, the show is more than a series of outlandish headlines—it’s a masterclass in quick-witted group comedy and observational humor, held together by decades-long chemistry and an unashamed love of the absurd.