Holmberg's Morning Sickness — Josh Wolf w/Son Jacob In Studio (Feb 5, 2026) Podcast: 98KUPD Arizona | Hosts: John Holmberg, Brady Bogen, Bret Vesely, Dick Toledo | Guests: Josh Wolf and son Jacob Wolf

Overview

In this episode, comedian Josh Wolf joins John Holmberg and the Morning Sickness crew with his son Jacob Wolf, promoting their dual stand-up shows in Tempe and chatting about life, family, comedy, and wild stories on (and off) the road. The tone is loose, irreverent, affectionate, and extremely funny, as Holmberg and Josh riff about names, stage antics, substance-fueled shows, and father-son dynamics in the entertainment biz.

Key Discussion Points & Insights

Introductions and Name Jokes

• [00:24–04:38]: Josh and Jacob are introduced, sparking a skit about Jacob's childhood and naming conventions.
  • The group jokes about the tradition of adding “Jr.” or “Sr.” to names, with Josh ribbing about how he almost named Jacob after himself.
  • Holmberg: “You’re an entertainment mullet — nepotism in the front, trafficking in the back.” (02:43)
  • Josh and Jacob riff on getting called “Wolf Jr.” and entertaining in the shadow (and favor) of a famous parent.

“Bio Mom” and Family Comedy

• [03:09–06:56]: Holmberg recalls nearly being named “Alvar Augustus Holmberg” and riffs about how much names can dictate fate.
  • Josh: “Well, you'd have been the best Dungeons & Dragons player of all time.” (05:54)
  • The group imagines what it would be like to have elaborate, stately names (with a running “bio mom” joke threading through).

Father-Son Podcast & Comedy Tour

• [09:42–10:22]: Discussion of their podcast, formerly called Hey Man, now “On the Road with Josh and Jacob.”
  • Jacob: “Basically because we’re together too much.”
  • They joke about being sick of each other offstage, saving their best material for the show.

Travel Antics & On-Tour Dynamics

• [10:46–12:01]: Classic stories of pranking each other on flights, from embarrassing sleep photos to who gets the hotel room alone.
  • Jacob: “I try to stay awake until he falls asleep first.” (10:46)
  • Josh: “He won’t sit next to me on the plane… that’s another thing when you do a show, you gotta save it.”

The Mushroom Show and Performing on Psychedelics

• [11:57–14:27]: Josh explains performing stand-up on three grams of mushrooms during a late set.
  • Josh: “Friday night, late show, I take all my three grams and I go on stage.” (12:01)
  • Jacob provides backup offstage, sometimes needing to jump in if Josh gets too “high” to function.
  • Jacob: “I went out there at one point just to settle the nerves… He’s crushing!” (14:13)

Live TV Fiascoes — Shark Week and the Tara Reid Interview

• [14:47–19:29]: Josh recounts hosting Shark After Dark and a legendary interview with Tara Reid.
  • Tara believed a “whale shark” was from a whale and a shark mating.
  • Tara Reid: “So I thought a whale shark was when a whale and a shark have sex... but it turns out one of them is an animal and one is a mammal.” (17:49)
  • Josh (on his director): “Go to break… and I basically looked at the camera like, no way am I going to break.” (19:05)

Generational Differences & Boomer Humor (Bathroom Segment)

• [21:11–23:58]: Banter about aging, incontinence, and "grandpa balls."
  • Josh: “My grandfather said once...you'll have to hold them in your hand so you don't poop on them.” (22:05)
  • Embarrassing bathroom stories, including sitting when peeing and the logistics on airplanes, get lots of laughs.

Drug Use and Sober Living Stories

• [29:54–34:14]: Open talk about experimenting with drugs, including ketamine and mushrooms.
  • Josh shares the story of the first time he and Jacob smoked weed together — at Jacob’s request on his 18th birthday.
  • Jacob: “I was a drug addict and had a gambling problem… if I have a debit card, I'm going to be out of money way faster, so I didn't have a debit card to limit my gambling.” (32:06)
  • The crew discusses Jacob’s stint in a sober home and realizing he hadn’t gone as far down the rabbit hole as some others.
  • Jacob: “14 degenerates, one house – not a terrible MTV show.” (34:02)
  • Josh: “Who stays alive the longest? Awesome watching that one.” (34:09)

Game Show Concepts & Observations about Society

• [34:24–37:28]: Holmberg pitches wild (and definitely un-airable) Japanese game show ideas.
  • “For a million dollars, guess your dad—five glory holes and out come the wieners. You pick sight, touch, or taste.” (34:24)
  • Conversation about whether men or women fall in love more easily, women’s gold-digger instincts, and social experiment show formats.

Notable Quotes & Memorable Moments

• Holmberg: “You’re an entertainment mullet — nepotism in the front, trafficking in the back.” (02:43)
• Josh Wolf: “Friday night, late show, I take all my three grams and I go on stage.” (12:01)
• Jacob Wolf: “I try to stay awake until he falls asleep first. I’ve started doing the same thing.” (10:46)
• Tara Reid: “So I thought a whale shark was when a whale and a shark have sex... but it turns out one of them is an animal and one is a mammal.” (17:49)
• Holmberg: “Our grandfathers are cut from the same cloth. …I went to the bathroom at his house, and there’s this gigantic cushion… he goes, ‘I have to use that or my ball gets in the water.’” (22:05)
• Jacob Wolf: “14 degenerates, one house – not a terrible MTV show.” (34:02)
• Holmberg: “For a million dollars, guess your dad—five glory holes and out come the wieners. You pick sight, touch, or taste.” (34:24)

Important Timestamps

• 00:24–02:00 — Opening banter, Wolf family introductions, and jokes about cussing and nicknames
• 05:01–06:56 — Holmberg’s story about "Alvar Augustus" and the existential weight of a name
• 09:42–10:22 — Explanation of their podcast ‘On The Road With Josh and Jacob’
• 12:01–14:27 — Josh performing a stand-up show on mushrooms, with Jacob as his show “spotter”
• 14:47–19:29 — Josh relives hosting Shark After Dark and the Tara Reid “whale shark” interview
• 21:11–23:58 — Bathroom humor and "grandpa stories"
• 29:54–34:14 — Candid stories about drug use, Jacob’s year in a sober house, and generational dynamics
• 34:24–37:28 — Outrageous (parody) game show concepts and musings on social observation

Summary Highlights

• The chemistry between Josh and Jacob Wolf brings natural, rapid-fire comedy and genuine family warmth.
• Topics meander from the absurdity of names to truly bent game show concepts, but always loop back to a lighthearted, self-deprecating tone.
• Josh’s openness about performing comedy on various substances (mushrooms, ketamine) sets up honest — and hilarious — discussions about drug use and parenting.
• Jacob’s journey with addiction, gambling, and recovery is met with support and a generous dose of humor.
• Notable moments include the legendary Tara Reid live-TV gaffe and razor-sharp societal observations on how people behave when the stakes (or the money) are secret.
• The episode threads in recurring bits about “bio mom,” mock epic names, and the relatable awkwardness of getting older.

Final Note

Fans of stand-up comedy, family storytelling, and raw, rapid banter will love this episode. Josh and Jacob’s dynamic is hilarious and relatable, with plenty of behind-the-scenes looks at both the comedy grind and the real-life challenges of staying honest, connected, and a little bit weird.