The BOB & TOM Show Extra: Oskay's Hair & Beard Trim

Date: December 24, 2025
Podcast: The BOB & TOM Show Free Podcast

Episode Overview

This episode of BOB & TOM Extra centers around the comedic adventure of show regular Jeff Oskay getting a haircut and beard trim live in the studio. The crew, along with guest stylist Christine (married to show engineer Eddie), riff on Jeff’s impressive hair, his beard, and the transformation process. As always, the conversation spins off into hilarious sidebars touching on hair care, tipping customs, tattoos, and family banter, with trademark BOB & TOM irreverence and camaraderie.

Key Discussion Points & Insights

1. Jeff Oskay's Hair and Beard: The Main Event

• The episode kicks off with banter about Jeff Oskay's unruly hair and beard, prompting on-air commentary and playful jabs from the cast.
• (02:42) Josh Arnold admires Jeff's wet hair:
  "Jeff’s hair when it’s wet like that, like it’s got, you know… Looks great."
• (02:55) Tom Griswold exclaims:
  "It’s amazing. Yeah. I mean, it’s huge. I mean, it’s. It’s full. And you’re a man of a certain age with like 42 or something and plus 10 years..."
• Discussion turns to the physical transformations haircuts cause, with Jeff expressing concern about looking heavier with a clean cut and Tom comparing Jeff to Tom Hanks in Castaway (“Without the weight loss”).
  "Slick back hair. You look like a thug. That... you know, in some movie, you come and you kill somebody." (04:47, Tom)

2. Christine the Stylist and Her Artistic Vision

• Christine takes charge, describing her approach to Jeff's hair: longer on top, tight on the sides, and a blend into the beard.
  • (05:49) Christine: "I’m thinking something like we’re going to leave it a little bit longer on top and I’m not going to buzz the sides down, but it’s going to be pretty tight."
• Jeff grants her artistic license:
  "I told her she could do whatever she wants. She can give me a mohawk." (05:27, Jeff)
• Light teasing about the experience—how the haircutting process can sometimes be awkward or misunderstood.
  • (06:09) Tom: "Do you ever hear the story, ever hear the story about the... hair salon lady that called the cops cuz she thought the guy was jacking it? It turned out he was cleaning his glasses underneath the apron."

3. Product Talk and Hair History

• Jeff shares his hair routine, using “Jesse's Soft Curl,” with a riff on whether it’s a real product and references to past accusations of hair perms.
  • (06:32) Tom: "Now, Jeffrey, you say you were telling me this morning you put a so called product in your hair. Yeah. What is that called?"
  • (06:39) Jeff: "It’s Jessie's soft curl."
• Kristi Lee clarifies:
  "Yeah, it’s for curly hair... it enhances your curls." (06:41-06:46)
• Jeff clarifies his hair’s authenticity:
  "Many people thought I had my hair permed back in the 80s, but that was just my hair." (06:51, Jeff)

4. Musical Interludes and Oskay’s “Wizard of Oz” Moment

• Eddie provides improvised musical humor:
  • (07:08) Eddie sings a song about Jeff’s salon experience, riffing on "The Merry Old Land of Oz," but adapting it for Oskay:
    "He's in the shop for hair repair in the merry old land of Ozke..."

5. Tipping, Salon Culture, and Social Banter

• Christine is asked about tipping trends between male and female clients.
  • (07:54) Tom: "Who tips better? ...Men tip better or women tip better?"
  • (08:12) Christine (cheekily): "Well, it depends on what I'm wearing that day."
• Josh Arnold pushes further into taboo territory, quickly dialing it back after a laugh.

6. Family and In-Studio Dynamics

• Banter shifts to Christine being married to Eddie, the show’s engineer. Jokes about their mixed-race marriage ensue, handled with classic BOB & TOM levity.
  • (09:01) Josh: "So you’re in a mixed relationship?"
  • (09:13) Tom: "He’s going to be replacing that guy in Journey. Good." (a joke about Eddie’s Filipino heritage and Steve Perry’s replacement in Journey)

7. Distracting, Offbeat, and Behind-the-Scenes Humor

• The crew plays with Jeff’s hairstyle mid-cut, including parting his hair like Moses, evoking a barbershop quartet look, and doing faux singing routines.
  • (10:03) Tom: "Can you do me a favor, Christine, for a second? Can you part his hair in the middle like Moses?"
  • (10:18-10:23) Group breaks out in barbershop-flavored jokes and singing.
• Sound of clippers sparks a tangent about hearing loss and Tom’s inability to hear certain frequencies, with Pat and Eddie chiming in.
• Jeff laments Christine’s “dollest clippers,” joking about the pain.
  • (11:10) Jeff: "She brought some of the dollest clippers she could find. It’s ripping every hair out of my neck."

8. Tattoos: Choices and Stories

• Talk turns to tattoos—Jeff has a Libra sign tattoo, which the group teases him about.
  • (11:58) Jeff: "It basically looks like I have a hanger hanging out of the back of my shirt. It looks stupid as..."
• Tom tells a funny story about his daughter questioning family tattoo policy and inheritance.
  • (13:38) Tom: "At dinner a couple of weeks ago, she goes, dad, you said that if your kids get tattoos, they're not gonna be in the will. So does this mean that Finn and I get all the money?"

9. Show Finale: The Big Reveal and Final Banter

• As the trim wraps up, the group reviews Jeff’s new look, giving both good-natured ribbing and compliments.
  • (15:26) Josh: "Man, look at how handsome he is."
  • (15:29) Jeff: "Look at me go."
• More jokes about further grooming, including a jab at “Eddie's pubes,” which the group quickly squashes as they burst into laughter.
  • (15:40) Josh: "She's doing your pubes after this. What are Eddie's pubes like?"
• They joke about Christine and Eddie's children and family resemblance, with playful queries about DNA tests and their son’s remarkable height (over 7 feet.)

Notable Quotes & Memorable Moments

• On Oskay’s Hair:
  "You look like a thug. That... you know, in some movie, you come and you kill somebody." — Tom Griswold (04:47)

• On Salon Tipping:
  "Well, it depends on what I'm wearing that day." — Christine (08:12)

• On Product Usage:
  "It's Jessie's soft curl." — Jeff Oskay (06:39)

• On Family Tattoo Policy:
  "Dad, you said that if your kids get tattoos, they're not gonna be in the will. So does this mean that Finn and I get all the money?" — Tom Griswold's daughter (13:38)

• On Hair Pain:
  "It's ripping every hair out of my neck." — Jeff Oskay (11:10)

Timestamps for Key Segments

• 02:21 – Oskay’s hair revealed, opening jokes
• 03:32-04:12 – Discussion of beard color, appearance, and comparison to Castaway
• 05:49 – Christine explains her haircutting vision
• 06:32-07:06 – Product discussion and hair routine
• 07:08-07:49 – Eddie’s hair salon musical bit
• 07:54-08:12 – Tipping habits, salon culture
• 10:03-10:23 – Barbershop quartet hairdo and song riff
• 11:10 – Complaints about dull clippers
• 11:48-12:30 – Oskay’s tattoo story
• 13:38 – Tom’s family tattoo/will anecdote
• 15:26-15:31 – Group admires Oskay’s new look

Episode Tone and Style

The episode brims with the high-spirited, rapid-fire banter and irreverent, affectionate teasing that define The BOB & TOM Show. The in-studio camaraderie is palpable. Laughter, gentle mockery, and absurdism reign, with the cast and guests rolling with every tangent. The show’s staples—hair, family, aging, and offbeat personal stories—are all mixed in with a healthy dose of self-deprecation.

Takeaway

For fans and newcomers alike, this episode is a classic display of The BOB & TOM Show’s ability to turn the mundane—in this case, a haircut—into a comedy free-for-all. With quick-witted guests and plenty of ensemble chemistry, it’s a fittingly fun and slightly chaotic listen for the holiday season.