Podcast Summary: The Wayback #89 | Steph Tolev
Date: September 11, 2025
Host: Ryan Sickler
Guest: Steph Tolev
Episode Overview
In episode 89 of The Wayback, Ryan Sickler sits down with comedian Steph Tolev for a wildly nostalgic journey through her childhood and adolescence. The conversation covers everything from embarrassing high school stories and family quirks to misadventures with early stand-up sets, teenage parties, and the evolution of her personal style. Packed with laughter, a few infamous incidents, and plenty of warmth, Steph lets loose on her formative years in a way only a comedian can.
Key Discussion Points & Insights
Steph’s Early Comedy and Netflix Special
- Steph promotes her Netflix special Filth Queen and encourages listeners to rewatch it.
"It's on Netflix. It's called Filth Queen. Please watch it if you haven't yet. If you have, just put it back on." (00:59 – Steph)
- She and Ryan share stories of their earliest stand-up sets and how cringeworthy they were in retrospect.
“My opening joke used to be, sorry I’m late, I came on 30 seconds after my nose. Oh, God, so bad!” (04:09 – Steph)
The "Wayback Machine": Childhood Cars and Dance Memories
- Steph reminisces about riding in the backward-facing backseat of an old station wagon, often getting carsick on the way to dance competitions.
- Shares a humorously mortifying story about filming herself mocking a friend’s family’s dirty house, only for the tape to be discovered and shown years later.
"They played it...years later, like, no, not that far down the line. And they call my parents, like, I think Stephanie owes us an apology. I was so rude." (02:10 – Steph)
High School Antics: Arrest, Suspension, and Tattoos
- Tolev describes her formative years at East York Collegiate Institute, a family legacy school, and being handcuffed and briefly expelled in grade 11 after a hallway fight, wrongly accused of a hate crime.
“I got arrested for assault. Me and my friend. It was my fault. I started the fight verbally...She pushed me and I was like, excuse me. And then I pushed her back. And then my other friend came in and we got in a bit of a tussle, a couple punches to the head.” (06:07 – Steph)
- She and her friend later get matching tattoos of handcuffs to commemorate the arrest.
"My friend and I who got arrested together...we went and got these ey. Tattoos and we also got handcuffs." (12:00 – Steph)
- Despite the trouble, Steph makes a point of saying how involved she was: in plays, sports, student government, even as the high school mascot (a bulldog, which she played mischievously).
"So after I got arrested...I got in everything. I was on student government. I was in all the fucking plays. I was on the announcement crew...I was the MVP the lacrosse team." (12:08 – Steph)
Phases, Fashion, and Embarrassing Moments
- The duo laughs over high school and middle school fashion fads—Steph describes being a "Gina" (Greek-inspired style), then transitioning through skater and punk phases.
"Grade nine, big hoop earrings, tight little crop tops when I went out...Then grade ten, I was wearing like big like puka shell necklaces. I had like Roxy everything." (13:44 – Steph)
- Memorable story: Steph trying to escape a massive concert (SARSstock) crowd, only to get her skirt caught on a fence and expose her underwear to thousands.
"...my skirt gets caught on the back of this fence. I start dangling...full granny panties are ripped in my ass. All these people...are pointing and laughing at me. I can't get down." (19:14 – Steph)
Growing Up: Dancing, Family, and Cars
- Childhood consumed by travel for Scottish Highland dance competitions, thanks to her mom’s coaching career.
"Pretty much every weekend of my life was a dancing competition…We drove a lot to Pennsylvania. A lot of places." (24:42–24:55 – Steph)
- Details about family vehicles: fond memories of the green Dodge Caravan, later a Ford Escape, and inheriting a Plymouth Acclaim from her grandfather, which came with “fuzzy tits” as a gag car accessory.
"I found these two fuzzy tits. I thought they were so funny. I put them in the car." (25:37 – Steph) "When I first got it...a bunch of skin flakes came out because [my grandpa] had really bad psoriasis." (26:14 – Steph)
Pet Stories & Family Life
- Steph had numerous pets growing up—hamsters, golden retrievers—and shares how her dad broke the news about a hamster’s demise only years later for comic effect.
"It died to the song...Bittersweet Symphony...feeding it a piece of lettuce...the next morning I woke up and it was gone...my dad told me like two years ago that my dog immediately ate it." (27:06 – Steph)
- She and her sister had separate rooms, and their weekends were filled with dance or adventures in the Don Valley.
Teenage Parties: The Secret Life of Steph’s House
- Once given freedom as a teen, Steph threw epic house parties but imposed strict house rules: no shoes and no smoking. She would meticulously clean up to avoid detection.
"I made everyone take their shoes Off. I'd have hundreds of people at the house. Everyone's shoes were off. You come in, there's no smoking, there's no shoes. Those are the two rules." (30:16 – Steph)
- She was caught only because a neighbor stepped in, but he promised not to rat her out.
"Don comes over...and Don's like, Stephanie, this is it...I promise you, I will not tell them, but you can't do this again. And I never threw another party. And Don never said anything." (32:13 – Steph)
Cleaning Mishaps & Parental Expectations
- Steph relays a tale of cleaning a deck so well after a party mishap that her father had to power wash the rest to match.
"My dad calls me up. He goes, what the did you spill on that deck?...I had to power wash the rest of the deck to get it to match." (34:23 – Steph)
- The conversation ends with mutual appreciation and plugs for Steph’s special.
Notable Quotes and Memorable Moments
- On early comedy:
"If this ever sees the light of day, you will hear from my lawyers." (04:03 – Steph, about her first standup tape)
- On parental expectations:
"How could you fight with my father when he’s wearing banana shorts?" (23:52 – Steph)
- On partying:
"Getting alcohol is the easiest thing on the planet…We used to do a thing called dial a bottle." (28:55–29:05 – Steph)
- On cleaning after parties:
"The guy lifted up and he went, holy—what the—my parents like, what? It's all stains, red, black, brown." (30:14 – Steph)
- On the viral potential of embarrassing moments:
"Thank god this is before cell phones. My ass would have been all over." (20:20 – Steph, on her SARSstock moment)
Timestamps for Important Segments
- Steph’s Netflix special and early standup: 00:54–04:29
- Family car memories and the infamous tape: 01:15–03:20
- High school, arrest, hate crime accusation: 05:00–11:39
- Phases and fashion stories: 13:03–18:00
- SARSstock skirt disaster: 18:00–20:20
- Family travel and dance memories: 24:08–25:13
- Inheritance of the Plymouth Acclaim: 25:36–26:14
- Pet stories: 27:06–27:39
- Throwing house parties and party aftermath: 30:16–32:55
- Cleaning mishap at the cottage: 32:59–34:23
Closing Remarks
The episode is a rollicking, hilarious look into Steph Tolev’s youth, filled with outrageous situations, endearing family details, petty teenage rebellion, and the kind of awkwardness everyone can relate to. Both host and guest let the conversation breathe, diving deep into nostalgia without pulling any punches.
Final Plug
- Steph:
"Watch my Netflix special if you haven’t…Filth Queen. Come see me live. I’m funnier live." (34:38 – Steph)
- Ryan:
"You’re funny always." (34:45 – Ryan)