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)
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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)
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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)
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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)
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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)
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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)
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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)
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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)
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Water Fountain Hazing:
- They reminisce about the trauma of school water fountains, getting their heads jammed, and tricks involving gum.
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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)
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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)
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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)
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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)
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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)
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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)
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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)
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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)
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Firework Pranks and Pizza Place Mayhem:
- Fond/chaotic memory of throwing cherry bombs in a pizza restaurant, and pelting the owner with a pie.
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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.
