The Wayback with Ryan Sickler

Episode 87: Craig Shoemaker
Release Date: August 28, 2025

Episode Overview

In this nostalgic, laughter-filled episode, comedian Craig Shoemaker joins Ryan Sickler for a wild ride through their childhoods, revisiting misadventures, pranks, and the untamable spirit of growing up in the 70s and 80s. Together, they celebrate the highs and lows of adolescence—stealthy pool-hopping, desperate attempts to fit in, near-mythological buildings, and the goofy genius of kid logic. From scrappy “dungeon gang” parties to close calls with the law, this is a love letter to a misfit upbringing and the enduring bonds of friendship.

Key Discussion Points & Insights

1. Growing Up in the Era of the “Wayback” (MM:40)

• Woodie Wagons and Rear-Facing Seats:

  • Craig reminisces about sitting in the "way back" of his grandfather's Woodie—facing backwards and making faces at other drivers.
  • “You make fun of the people behind you, hoping they give you the finger.” — Craig Shoemaker (01:49)

• Car Culture and Free Paint Jobs:

  • Ryan shares about his family’s rusting red VW Beetle, which got a free paint job from Yellow Pages—if you plastered their logo on every surface. (02:50-03:34)
  • “When they peeled that off, it looked like there had been stickers. It was terrible.” — Ryan Sickler (03:19)

2. Kids’ Schemes: Drive-Ins, Pool Hopping, and the Dungeon Gang (03:37–09:42)

• Drive-In Movie Tricks:

  • Both recall hiding in trunks (front and back) to avoid entry fees—sometimes through entire movies!
  • “I was like, we’re bumping along and I’m trying to be quiet…but that’s how we got into things.” — Craig (03:55)

• Pool Hopping and Forts:

  • Entry to in-ground pool homes required befriending specific kids; the hosts laugh about the unspoken social hierarchy.
  • Craig tells of the “Dungeon Gang”—his crew’s tricked-out garage party spot. (06:02)
  • “We had strobe lights, lava lamps, everything…for the girls who…eventually, we thought would come. Yeah, it was dudes.” — Craig (07:13)

• Ball-Busting Friendship:

  • Both agree affection was shown by relentless teasing and giving nicknames.
  • “That’s the expression of love…If I tease you, if I look for things to tease you…a nickname is a real affection thing.” — Craig (08:40)

Memorable Moment:

• The "Naked Door Rip" Prank — Craig recounts how the Dungeon Gang knocked on doors, roasted strangers, and streaked through a rich neighborhood, highlighting the wacky stunts that bonded the gang.
  • “Wait till they answer, make fun of them…And while we’re nude.” — Craig (10:11)
  • “Get the coffin ready, you old bag!” — George (Craig’s friend) (11:10)

3. Breaking and Entering: Mansions, Mini-Golf, and Sanatoriums (16:33–24:40)

• Stoatsbury Mansion Mischief:

  • Craig recalls exploring the enormous, now-razed Stoatsbury Mansion in PA, giving “tours to hippies” for 50 cents, and evading cops through attics.
  • “It is a mini Versailles. It’s funny you say that’s modeled after Versailles.” — Craig (17:14)

• Urban Legends and TB Hospitals:

  • Both discuss sneaking into creepy abandoned buildings—Ryan’s Mount Wilson Hospital in Maryland, said to be haunted, and full of graffiti and wheelchair-pentagrams.
  • “It was like somebody walked in on Thursday at 2:30—like, they cured everybody and everybody just went, ‘we’re gone.’” — Ryan (23:28)

4. Bullying, Nicknames, and the Perils of Childhood (25:45–32:37)

• Water Fountain Hazing:

  • They reminisce about the trauma of school water fountains, getting their heads jammed, and tricks involving gum.

• Bullying and Wedgies:

  • Craig speaks candidly about being a bullied, scrawny kid in a family of girls, and the infamous wedgie hung from a locker.
  • “I was a wedgie waiting to happen...They hung me from a locker in school by my underwear.” — Craig (25:45)

• Finding Acceptance through Misfit Brotherhood:

  • Eighth grade was especially tough until Craig found his “Dungeon Gang”—a tribe of lovable rejects.

5. Sports Misadventures & Sweet Defeats (29:19–32:37)

• Craig's Football Fiasco:

  • At 5’1”, Craig finally got into a high school football game, and accidentally ended their shutout streak by letting the opposition score a 62-yard touchdown!
  • “My goal…get my uniform dirty…so my mom should be proud. But no one knew me, including [the coach]!” — Craig (30:25)

• Stadium Security & Surprise “Reward”:

  • After getting roughed up by stadium security for sneaking into the broadcast booth, Craig's friend is so bloodied, they end up getting free game tickets to avoid a lawsuit. (28:45)

6. Crime, Pranks, and Parental Absurdity (32:44–37:45)

• Shoplifting Antics:

  • Craig admits to childhood delinquency: “I got arrested for shoplifting…The cop says, ‘How would you like to end up with one of these guys on a poster?’ I’m going, at least he’s wanted!” (33:02)

• Absurd Parental Gestures:

  • His father notoriously “gave” Craig a car for his 16th birthday—then took it home himself, leaving Craig with only the title. (35:59)
  • “He gave me the car. He took the car.” — Craig (36:29)

• Creative Junkmobiles:

  • Craig had a 66 Cadillac ambulance as a “moving dungeon,” complete with broken parts but perfect for teenage mischief.

7. Rich Kids, Cherry Bombs, and Social Hierarchies (39:50–44:05)

• Class Divides in Suburbia:

  • Craig reflects on befriending richer kids for access to amenities—and the white lies he had to tell when his "pool" turned out to be a creek.
  • “They said, ‘Do you have a pool?’ I go, ‘Yeah, I got a pool!’…It was the creek in the back in Dosher’s woods.” — Craig (41:53)

• Firework Pranks and Pizza Place Mayhem:

  • Fond/chaotic memory of throwing cherry bombs in a pizza restaurant, and pelting the owner with a pie.

• Reunion with Old Friends:

  • A reunion decades later proves childhood gaffes are never forgotten.
  • “Remember the time you invited us over, you cherry pops and swimming…and you said the creek is where you swim. They literally left. I never saw them again. And that’s why I’m a comedian.” — Craig (43:47)

Notable Quotes & Memorable Moments

• “If I tease you…a nickname is a real affection thing. Shorten your last name. That’s your last name. You didn’t have a good one for that?” — Craig Shoemaker (08:40)
• “We’d rip on each other so bad…that was the best. That’s why—also these days—I know we sound like old men, but kids are soft today.” — Ryan Sickler (08:21)
• “She opens it. George goes…and we freeze. Who’s got the first line?…I do the penis helicopter. Hey, lady, penis helicopter… George goes, ‘get the coffin ready, you old bag!’” — Craig recounting a wild prank (11:02)
• “My father’s only memory of his father is waving to him through the window.” — Craig on family tragedy tied to tuberculosis (22:48)
• “I got arrested for shoplifting…The cop says, ‘How would you like to end up with one of these guys on a poster?’ I’m going, at least he’s wanted!” — Craig (33:02)
• “He gave me the car. He took the car.” — Craig (36:29)

Timestamps for Major Segments

• 00:40–02:30 — Childhood car memories, Woodie wagons, making faces at drivers
• 03:37–06:27 — Drive-in trunk schemes, pool hopping, the genesis of the Dungeon Gang
• 10:09–13:23 — The “Naked Door Rip” stunt
• 16:31–19:08 — Adventures in Stoatsbury Mansion, giving ghostly tours
• 23:25–24:40 — Sneaking into abandoned hospitals, terrifying themselves with urban legends
• 25:45–28:45 — Bullying, wedgies, and sports humiliation
• 29:19–32:37 — Craig’s infamous football fail
• 32:44–37:45 — Early run-ins with the law, parental weirdness, and car stories
• 41:30–44:05 — Suburban class divides, cherry bomb gags, and failed attempts at popularity

Episode Tone & Language

The episode is loose, candid, and brimming with laughter and affectionate ball-busting. Both Craig and Ryan riff off each other as only old friends (or fellow mischief-makers) can, swapping war stories with equal parts warmth and irreverence. Their storytelling bursts with vivid detail, off-the-wall physical comedy, and genuine reflection on how their backgrounds shaped them and their comedy.

Where to Find Craig Shoemaker

• Website: craigshoemaker.com
• Socials: Official Craig Shoemaker on Instagram, LinkedIn, and more
• Business: laughterworks.com (corporate comedy and resilience workshops)

This is a can’t-miss, memory-rich episode for anyone who’s ever been a teenage knucklehead. Expect big laughs, big heart, and enough “kids these days” wisdom to fill a Woodie wagon.