The Wayback with Ryan Sickler

Episode 90: The Wayback #90 | Ali Siddiq
Date: September 18, 2025

Episode Overview

In this episode, Ryan Sickler welcomes back comedian Ali Siddiq for his second nostalgic journey on "The Wayback." Together, they revisit childhood memories—ranging from unconventional “vacationing” and wild neighborhood games to school dances, the agony and glory of early video games, and fiercely competitive family moments. Packed with humor, vivid recollections, and moments of reflection, this episode is a ride through Ali’s formative years and the joys and absurdities of growing up in the '80s.

Key Discussion Points & Insights

Childhood "Vacations" & Family Dynamics

• Ali Siddiq shares that his family didn’t take traditional vacations.
  • Instead, when his mother needed to work or get settled in a new career, he and his sister were sent to live with relatives in different cities, which became their version of a "vacation."
  • Ali: "So that was our vacation." (04:08)
• Frequent moves between family in California, Mississippi (Clarksdale), Chicago, New York, and Louisiana.
  • Enrolled in at least seven elementary schools; never stayed in one place for long.
  • Ali: "No, these for whatever. For life. Like, we not getting...this is a until situation. This is like being locked up for...Yeah, they like, hey, you got 10 years in a day. Like what day? Just whenever we decide." (05:01)
• Memorable childhood injury:
  • As a small child zipped himself in his pants—prompting a hospital visit.
  • Lighter moment: “...is this General Hospital?” (07:17)

School Days & Social Life

• Ali’s revolving door of schools:
  • Never attended a full run (K-5) at one elementary school.
  • Built unique memories in each—his first Halloween in LA, trick-or-treating in Hollywood, and being terrified by a witch at a fancy house (08:13).
• School traditions and crushes:
  • Became a school flag-raiser to spend time with Tammy, his elementary school crush.
  • Ali: "This what made me want to do it. I...I needed that time. I needed that personal time." (14:32)
  • Fondly remembers learning about yellow rice from Tammy.
  • Explains experiencing the Challenger shuttle disaster by lowering the flag to half-mast.
  • Ali: “That was my first time ever having to lower the flag at half staff.” (16:22)
• School dances:
  • Breakdancing was king, driven by ‘80s movies like "Footloose," "Beat Street," "Fame," and Michael Jackson’s influence.
  • Ryan: "I mean, I still remember watching the moonwalk live and just being like, what was that? Was that an alien?" (19:17)

Athletic Aspirations & Middle School Sports

• Football & Basketball:
  • Played middle school football and basketball at Jane Long Middle School (“like Lawrence Taylor…we meant to hurt you”) (08:25).
  • Transferred to Paul Revere Middle School—experienced a more affluent environment (no bars on the windows), free basketball shoes, and themed game entrances (Beastie Boys’ “Paul Revere”) (09:44, 10:12).
• Notable teammate: Edgar Rice, “dunking in middle school,” but had to stop playing after 6pm due to his religious beliefs, costing the team wins (10:22).
• Height disadvantage:
  • Ali was a center in seventh grade, but didn't get taller—forced to transition to guard as others shot up in height.
  • Ali: "I've been five, seven since seventh grade." (12:42)

Neighborhood & Made-Up Games

• Impromptu games with neighborhood kids:
  • "Hot Ball"—throwing any object in the air, running touchdowns surrounded by a mob of tacklers (20:47).
  • Discussions on the game’s many names (East Coast called it "Smear the Queer", Ali’s group would never use that term).
  • "Spread Eagle" and "Butts Up"—rough, sometimes painful wall-ball games with unique (often brutal) punishments for losing (23:12).
  • Ali: "We really wanna hit you in the face or the head." (23:42)

Retro Video Game Culture

• Early gaming exposure:
  • Pinball before Pong, then on to Atari and classic arcade games—Galaga, Donkey Kong, Dig Dug, Track & Field, Pitfall, Double Dribble (24:24-30:12).
  • Ultra-competitive “track and field” controller burnouts, and even family fistfights over turn-taking (26:13; 27:30-28:10).
  • Ryan: "I had a twin brother...We would fist fight each other for that fucking game." (29:16)
• Handheld electronics and calculator nostalgia:
  • Playing with "Little Professor Calculator" and stealing batteries from household objects for more game time (28:58; 29:10).

Lifelong Competitiveness

• Ali describes being highly competitive, especially with his kids:
  • No mercy in family games—from chess to arcade basketball and table hockey (30:44).
  • Ali: "I dunk on my kids. I don't care about [that]. You are the competitor." (31:10)
• Extends to friends and tour crew:
  • Describes dominating everyone at the mall arcade shooting game (33:19).

Notable Quotes & Memorable Moments

• On “vacations”:
  • “My mom…she would send me and my sister to live with our relatives. So that was our vacation.” — Ali Siddiq (04:08)
• Getting sent away:
  • “This is like being locked up for…Yeah, they like, hey, you got 10 years in a day. Like what day? Just whenever we decide.” — Ali Siddiq (05:01)
• On being the school flag-raiser:
  • “This was the prettiest white girl I’ve ever seen in my life. And she was the flag bearer. And this what made me want to do it. I…Cuz I needed that time. I needed that personal time.” — Ali Siddiq (14:32)
• Challenger disaster memory:
  • “That was my first time ever having to lower the flag at half staff.” — Ali Siddiq (16:22)
• On childhood games:
  • “We just wanted to hurt each other. Cause definitely.” — Ali Siddiq, on how rough backyard games got (21:44)
• Neighborhood sports competitiveness:
  • “We was like Lawrence Taylor…We meant to hurt you.” — Ali Siddiq (08:25)
• On transitioning sports positions:
  • “I've been five, seven since seventh grade.” — Ali Siddiq (12:42)
• Video game memories:
  • “I had a twin brother…we would fist fight each other for that fucking game.” — Ryan Sickler (29:16)
• Parenting philosophy:
  • “I dunk on my kids. I don't care about [that]. You are the competitor.” — Ali Siddiq (31:10)
• Arcade sharpshooter:
  • “All of them have lost to me...I'm very competitive, man.” — Ali Siddiq (33:47–34:13)

Highlighted Timestamps

• 03:27 – Ali Siddiq returns, intro banter
• 04:08–05:55 – Childhood “vacations” and getting sent to live with relatives
• 07:04 – Childhood “entanglement” injury and General Hospital memory
• 08:13–08:22 – First Halloween in LA, terrified by a witch at a Hollywood house
• 09:23–12:13 – Middle school sports and realities of changing schools
• 13:52–16:57 – School flag-raising, crush on Tammy, Challenger disaster memory
• 17:41–19:10 – School dances, pop culture dance influences, Michael Jackson
• 20:47–24:15 – Neighborhood games: Hot Ball, Spread Eagle, Butts Up
• 24:24–30:40 – Video game history, early systems, competitive moments
• 30:44–34:13 – Family competitiveness in arcade games, shooting prowess
• 34:13–34:37 – Farewells and self-promotion

Tone & Atmosphere

This episode is infused with warmth, playful nostalgia, and raw honesty—Ali’s storytelling is candid and filled with humor, while Ryan matches him beat-for-beat in sharing vivid, often absurd, childhood recollections. Both host and guest wear their upbringing and competitive spirits on their sleeves, painting a riotous and heartfelt portrait of growing up in a different era.

Useful for New Listeners

Even if you missed the episode, this summary gives you a clear and engaging sense of the conversation’s highlights, the personalities involved, and the memorable cultural touchstones that shaped Ali Siddiq’s—and a generation’s—childhood.