The Wayback with Ryan Sickler

Episode 106: The Sickler Brothers | Baltimore Junkyard Series #106 | Part 1

Release Date: January 8, 2026
Host: Ryan Sickler
Guests: Todd Sickler, Derek Sickler (Ryan’s brothers), additional family friend(s)

Episode Overview

This much-anticipated episode marks the kickoff of Ryan Sickler’s “Baltimore Junkyard Series.” With listeners clamoring for years to hear from his brothers, Ryan brings Todd and Derek onto the show for an unscripted, nostalgic, and very Baltimore sit-down. The episode is a blend of unfiltered family stories, neighborhood memories, and hilarious recountings of childhood mischief, with a heavy emphasis on laughter, sibling dynamics, and the oddities of growing up Sickler.

Key Discussion Points & Insights

1. Sickler Family Updates & Health

• Todd’s Recent Surgery
  • Ryan kicks off by revealing Todd recently underwent triple bypass surgery:

    "He rerouted his like they rerouted that key bridge traffic." (04:00)

  • The siblings share gratitude that Todd made it through, adding a comedic touch throughout.

2. Childhood Twin Hijinks

• Identical Outfits and Parental Eccentricities

  • Ryan jokes about being fraternal twins with Derek but sharing identical twin beds, matching clothes:

    "To take two totally different looking people and dress them identically. It makes no sense..." (04:39)

  • The group recalls their mother sewing their names on shirts—ironically, after national warnings about child kidnappings involving named clothing (05:39–06:20).

• Sibling Pranks & Gross-out Games

  • Ryan and Derek reminisce about tormenting Todd by whispering his name at night (06:20–07:20).
  • The infamous “boogie flicking” and other nocturnal shenanigans are recounted to everyone’s disgust and laughter.

3. Bedwetting, Buzzers, and Divorce

• Family Challenges and Compassion
  • Open discussion about bedwetting tied to divorce stress; use of a medical “buzzer” system described in detail:

    "It’s effectively training you to wake up before you pee yourself. And it 100% worked for both of you." (08:21)

  • Siblings joke about ongoing adult precautions ("I got a plastic sheet on my bed right now…") (08:06) and sleepover anxieties.

4. Vintage Cars & Baltimore Stories

• Volkswagen Bug & Family Vehicles
  • Playful debate on car colors and childhood memories of family vehicles with branded decals (09:33–10:30).
  • Hilarious account of their mom’s attempt to win a Chrysler Laser by tossing a football at a radio promotion—unsuccessful, but immortalized:

    "I mean, I don’t think that shit made five yards." (12:25)

  • Reflections on being “celebrities” in elementary school after an on-air contest where they almost won an Atari (13:13–14:41).

5. Slapstick & Suburban Mayhem

• Backyard Animal Catches

  • Tales of setting up box traps for birds and rabbits ("That’s the moment I learned rabbits scream...") (16:02–17:20).
  • Comic memories of accidentally walking a blue jay and catching odd pets.

• Bingo with Grandma

  • Scenes from bingo nights at the Sykesville Fire Hall, with a Daniel-san Karate Kid figure knocking chips off serious players’ cards:

    "He’s just karate kidding on the table, knock—some lady’s chips fall off her card." (18:42–19:11)

6. Dad, Crabbing, and Never-Quite-Smooth Plans

• Fishing Fiascos
  • Recollections of attempting to crab with their dad: lines flying off boats on Route 50, propeller mishaps, the infamous smell of pickled “bull lips.” (19:41–20:44)
  • Frustration and laughter over plans that never quite worked out—a persistent theme:

    "We always had a good plan, but...I don’t ever remember it going smooth every time." (20:14–20:21)

7. Extended Family, Social Workers, and Resilience

• Improvising Grandma and Will He Talk?

  • Grandma’s on-the-fly bedtime storytelling, with improvised characters like "Skunk Tooth" and "Jacob Boot" (21:04–21:12).
  • The kids’ destruction of the ventriloquist doll, “Will He Talk,” in repeated window-throwing sessions.

• Favorite Aunts, Lawn-Chair Walkers

  • Aunt Mary’s hallmark line about their mother:

    "People treat their dogs better than she treats you kids." (22:07)

  • Anecdotes about pride, makeshift walkers, and absurd home decor (22:25–22:37).

• Heat, Attic Fans, and 100° Summers

  • The brothers laugh about unbearable summers, failed attic fans, and their drive for air-conditioning (22:48–23:23).

8. Bad Driving, Bumper Hook-Ups, and Broken Horns

• Minor Traffic Disasters

  • Their mom accidentally hooking one car bumper to another and their dad’s enraged, underdressed responses on frigid mornings (24:52–25:35).
  • Chronic abuse of the car horn by Ryan, culminating in their dad severing the horn line with a buck knife:

    "I was like, that motherfucker’s a man. He knew where the horn was. He just cut that." (27:35)

• Christmas Stolen by Baltimore

  • Story about the station wagon being broken into and all Christmas presents being stolen downtown:

    "That’s what I tell people all the time: Baltimore stole Christmas." (26:46)

9. Close Calls and Mistaken Guilt

• Wrongly Accused & School Troubles
  • Derek tells of being wrongly suspected of drug dealing after a false tip resulted in his car being searched and his locker moved (32:06–33:56).
  • Ryan’s sharp rebuke to the principal about failing the family post-father’s death is an emotional high point:

    "You leave that kid alone. This family’s been through enough. You did nothing for my brother and I when our father died. Not one goddamn guidance counselor meeting..." (33:24)

10. Quirky Family Members & Oddball Trivia

• Uncle John & the Purple Haze

  • Uncle John’s unwavering habit of painting everything purple (“Even the Orioles bat came back purple...”) (30:36–31:28)
  • Irony that Uncle John never lived to see the Ravens turn Baltimore purple.

• Lack of Parental Affection

  • The siblings reflect on never seeing their mom and dad show affection, leading to running jokes about the “romance” in their family (34:53–35:17):

    "That’s where I committed suicide. But I love you guys. I love you guys." (35:16–35:24, attributed to their dad’s sense of humor)

Notable Quotes & Moments

• On Todd’s Surgery:

  "He rerouted his like they rerouted that key bridge traffic."
  — Ryan Sickler (04:00)

• On Sibling Pranks:

  "He's picking his boogies and he's rolling them and he's just—I thought that was on second copy in the face. It probably kept going..."
  — Todd Sickler (06:52)

• On Bedwetting & Buzzers:

  "It’s effectively training you to wake up before you pee yourself. And it 100% worked for both of you."
  — Ryan Sickler (08:21)

• On Mom’s Chrysler Laser Attempt:

  "I mean, I don't think that shit made five yards."
  — Ryan Sickler (12:25)

• On (Almost) Winning the Atari:

  “Derek was a celebrity of Freedom elementary the next day.”
  — Ryan Sickler (13:25)

• On Bingo Mishaps:

  "He’s just karate kidding on the table, knock—some lady’s chips fall off her card."
  — Ryan Sickler (18:42)

• Aunt Mary’s Signature Line:

  "People treat their dogs better than she treats you kids."
  — Aunt Mary, recounted by Ryan (22:07)

• On Dad’s Patience:

  "I was like, that motherfucker’s a man. He knew where the horn was. He just cut that."
  — Ryan Sickler (27:35)

• On Family Dynamics:

  "Do you ever remember seeing mom or dad kiss or hug or affection in any way? No. Not at all."
  — Family, group (34:53–35:02)

• Dad’s Dry Humor Passing Site of Marriage:

  "That's where I committed suicide. But I love you guys. I love you guys."
  — Dad, mimicked by Todd and Ryan (35:16–35:24)

Timestamps for Important Segments

• Todd’s Health Update & Episode Kickoff: 04:00
• Identical Outfits & Parental Choices: 04:29–06:20
• Sibling Nighttime Pranks: 06:20–07:20
• Bedwetting & Buzzers: 07:27–09:13
• Volkswagen Bug Memories: 09:33–10:30
• Mom’s Chrysler Laser Football Attempt: 10:41–12:39
• Atari Contest Letdown: 13:13–14:41
• Animal Trapping at Grandma’s: 15:19–17:27
• Karate Kid Bingo Incident: 18:02–19:17
• Crabbing with Dad: 19:41–20:44
• Grandma’s Invented Bedtime Stories: 21:04–21:32
• Aunt Mary’s Tagline & Lawn Chairs: 22:02–22:37
• Summers in the Hot House: 22:58–23:23
• Car Mishaps & Horn Story: 24:52–27:48
• Stolen Christmas Gifts: 26:46–27:02
• Derek’s School Search Drama: 32:06–33:56
• Uncle John, Purple Paint Legend: 30:36–31:39
• Parental Affection Laughs: 34:53–35:24

Tone & Style

The conversation is deeply nostalgic, raw, and comedic, marked by the hallmarks of brotherly banter, self-deprecating humor, and loving irreverence. The siblings don’t shy away from acknowledging tough times (divorce, loss, brushes with trouble), but everything is delivered with a sense of resilience and warmth. Their stories capture the bittersweet, often ridiculous reality of growing up working-class in Baltimore.

Summary

This episode is a rich, laugh-filled trip down memory lane with the Sickler brothers, brimming with Baltimore quirks, sibling rivalry, and reflections on family dysfunction. From health scares and close calls to epic pranks and enduring bonds, it’s an openhearted, entertaining listen for new and longtime fans alike.