The Wayback with Ryan Sickler

Episode 108: My Twin Brother Derek | Baltimore Junkyard Series

Date: January 22, 2026
Guests: Ryan Sickler (host), Derek Sickler (twin brother)

Episode Overview

In this long-anticipated episode, Ryan Sickler welcomes his fraternal twin brother, Derek, for an unfiltered, nostalgic trip down memory lane through their childhood and teenage years in Baltimore. The brothers share wild stories, mischievous antics, and cherished moments as part of the new Baltimore Junkyard Series. The episode exudes their signature blend of humor, authenticity, and irreverence, peppered with sibling banter and raw detail. This is a true celebration of family, the complexity of growing up, and Baltimore roots.

Key Discussion Points & Highlights

1. Brotherly Introductions & Banter

• (03:49–05:23)
  • Ryan introduces Derek in Baltimore, fulfilling requests from fans to hear from his brothers.
  • Derek plugs his wife Sarah and children, Maddie and Tate, to which Ryan jokes, “That’s nice of you to give them a shout out, but I wouldn’t say plug my wife.”
  • Derek: “Why do I have the plug? I plugged her last night, man.” (05:17)

2. Childhood Memories: Iron Gate Era

Sibling Shenanigans, Shared Rooms, and Tormenting Todd

• (05:23–08:58)
  • The twins recount sharing a room and playing the "Todd" game with their younger brother, repeatedly whispering his name to drive him crazy.
    • Ryan: “He was too young to understand you could just ignore somebody.” (06:03)
    • Todd would yell to their mom: “Mom, they’re saying my name!”
  • Derek admits: “I remember smashing your KISS van out in the street.” (06:50)
  • They swap stories of toy destruction—Boba Fett dolls lost on rooftops, Star Wars figures with decapitated heads.
  • Tales of neighborhood trouble: Todd hurling a large rock at a neighbor’s Mercedes, brawling with Sean Flannery and friends.
  • Derek: “I remember going over one day... taking his dog and putting in the pool and it just sunk to the…” (08:32)

Family Discipline & Grandma’s Storytelling

• (10:43–13:13)
  • First and only time their dad “put hands” on them for cussing.
    • Derek: “That’s the only time I think he ever put hands on me.” (10:49)
    • Ryan: “You got to go first and I had to watch the abuse and then be like, oh my God, that’s coming to me next.” (11:23)
  • Grandma’s influence introducing them to storytelling and improv through made-up characters like “Jacob Boot” and “Skunk Tooth.”
    • Ryan: “I credit grandma all the time for introducing me to... early improv...” (12:08)

3. Chaotic Apartments: 7 Chase St.

The Sketchy Railroad Apartment & Odd Neighbors

• (15:39–18:40)
  • After their parents’ split, the boys move with their mom to a cramped, linear apartment.
  • Derek secures his own room—Ryan shares with Todd, joking that this is when he started “jerking it.”
    • “That was a mistake because that’s when I started jerking it. And I was shaking those bunk beds and I think mom was like, we gotta get them.” (15:58)
  • Encounters with bizarre neighbors: A schizophrenic man and “Sterling,” a “crazy little dude with the shorts and speech impediment.”

Petty Crime, Innocent & Not So Innocent

• (18:40–20:26)
  • They accidentally get grouped in with window-breaking kids but maintain innocence “at least that time.”
  • Door-to-door collecting cash “for Jerry’s kids”—a scam suggested by another kid; their dad forces them to wash the money for fingerprints and donate to Ronald McDonald House.
    • Derek: “We ripped off a shitload…” (19:18)
    • Ryan: “We started washing it and he was pissing himself...” (19:57)
    • Derek: “It was over 500 bucks.” (20:24)

Street Fights and Young Love

• (20:26–21:32)
  • Ryan stands up to bullies harassing Derek, escalating into a chain of street fights.
  • Ryan: “You ain’t touching my motherfucking bike or I'll get off this bike and beat your ass.” (20:52)
  • Reminiscing about first kisses and childhood adventures under bridges with “bums.”

4. Second Avenue & Teenage Escapades

Bike Jumps, X-Games Antics, and Neighborhood Kids

• (21:34–24:40)
  • A legendary BMX jump—Derek launches himself and trashes his bike, setting a “neighborhood record.”
    • Ryan: “That was the longest jump I’ve ever seen somebody make on a bike. It was X Games before X Games.” (24:28)
    • Derek: “Wheels, nothing got bent.” (24:40)

Driving, Failing, and Lessons

• (24:45–27:42)
  • Sibling rivalry over driving privileges—Ryan fails permit by a single question, Derek gloats.
    • Ryan: “You got to drive all the way home. And I was just pissed. You don’t remember that.” (25:03)
  • Taking the driver’s test in a stick-shift Honda in the snow, recalling their instructor's favorite lesson: “Wet leaves are like ice.” (26:14)
  • Their driving teacher illegally took them across state lines to buy lottery tickets.

5. Mischief, Pranks & Getting Caught

Mall Memories, Pranking Neighbors, and Parental Clues

• (27:53–30:40)
  • Shopping trips with their mall-obsessed mom; hiding in clothing racks at “Sixteen Plus,” scaring shoppers.
  • Pranking a neighbor named Mike by vandalizing his car with “whatever we had in the fridge: chocolate syrup... ketchup.''
    • Derek: “Anytime we were outside, it was doing something we should[n’t].” (30:07)
    • Dad detects incriminating evidence from sticky light switches.

Stealing The Car

• (31:43–34:49)
  • Classic sibling confessional: Derek steals the family station wagon as soon as their dad’s shift starts, gets caught almost instantly when dad returns for his work badge.
    • Derek: “Didn’t even let him get out the street before I went and got in the car... And I seen his badge... He's going to come back for this.” (32:33)
    • Dad pauses, says: “What the fuck do you think you’re doing?” (32:41)
    • Ryan: “I never did any shit like that... You stole it again.” (34:16)
    • Derek: “I took that car out probably a dozen times at least.” (34:20)

6. Childhood Dangers & Backyard Mayhem

BB Guns, Woodpeckers, and Snakes Galore

• (35:09–40:57)
  • Derek’s BB gun misadventures: “I had a scope on that BB gun. It was dialed in...” (35:18)
    • Ryan recounts the infamous “woodpecker execution” and Derek’s serial-killer tendencies (hanging the bird by a string for a fox to find).
      • Ryan: “To this day I laugh to myself just thinking, somewhere out in the woods there’s some old fox and he’s just arguing.” (36:13)
  • Derek’s lifelong ease with snakes: Catching, hiding, and pranking Ryan with them—including draping one over his neck during lawn mowing, and smuggling a garter snake inside a winter jacket.
    • Ryan: “That’s how I know I was a deep sleeper…” (31:43)
    • Ryan: “You throw it across the back of my neck.” (37:04)

7. Closing Reflections

• Sibling Rivalries, Closure, and Nostalgia

  • The twins revisit the infamous KISS remote-control van incident, finally (sort of) closing a childhood wound.

    • Ryan: “I want you to close that childhood wound for me and look right there at that camera and say, ‘Hey, Derek. Fuck you.’’' (41:14)

  • Ryan closes the show, thanking listeners for joining a different format, and inviting feedback to continue the "Way Back" series.

    • "Why sit here and do the same thing all the time? So I hope you guys are enjoying it, and if you are, throw a comment in there, let me know, and we'll keep on doing it." (41:45)

Notable Quotes & Memorable Moments (with Timestamps)

• Derek: “Why do I have the plug? I plugged her last night, man.” (05:17)
• Ryan: “We used to sit there and we just go... Todd... and he was, like, right next to us. He'd be like, ‘What?’ And then we wouldn't say anything. And we start. We just sit there laughing.” (05:55)
• On Dad’s discipline: “You got to go first and I had to watch the abuse and then be like, oh my God, that’s coming to me next.” (11:23)
• On childhood scams: “We started washing it and he was pissing himself... We took all that clean money to Ronald McDonald House in Westminster.” (19:57–20:11)
• Legendary bike jump: “That was the longest jump I’ve ever seen somebody make on a bike. It was X Games before X Games.” (24:28)
• On driving instruction: “Wet leaves are like ice. That’s all he says... Wet leaves are like ice.” (26:14)
• Derek on getting caught stealing the car: “Didn’t even let him get out the street before I went and got in the car... He jams on the brake and I stop...” (32:33)
• On the KISS van incident:
  • Ryan: “I want you to close that childhood wound... and say, ‘Hey, Derek. Fuck you.’’’ (41:14)

Important Segments & Timestamps

• [03:49] — Derek joins the episode
• [05:23–08:58] — Iron Gate childhood, pranks, fights, Grandma’s stories
• [15:39–18:40] — 7 Chase Street era, sketchy neighbors, first scam
• [21:34–24:40] — BMX jump, legendary crash
• [24:45–27:42] — Driving test and lessons
• [27:53–30:40] — Mall antics, pranking the neighbor
• [31:43–34:49] — Derek steals the family car and gets caught
• [35:09–40:57] — BB gun mayhem, shooting woodpeckers, snake pranks
• [41:14] — KISS van wound, closing and reflection

Tone & Style

The episode’s tone is rowdy, honest, and deeply nostalgic, with authentic Baltimore flavor. The brothers pull no punches, bouncing between heartfelt memories and crude humor—often at each other's expense. Their language is candid and colorful, making for a lively, relatable, and laughter-filled listen for anyone with siblings or a rough-and-tumble childhood.

For New Listeners

Even if you’ve never heard The Wayback, this episode stands alone as a hilarious and surprisingly moving look at family, forgiveness, and growing up in Baltimore. It delivers plenty of laughter but also celebrates the bonds that endure through chaos and mischief. Highly recommended for fans of raw storytelling and sibling revelry.