This Past Weekend w/ Theo Von

#659 - Ari Matti

with Ari Matti
22 May 2026 8 min read 1h 42m

Ari recounts his surreal first experience in Stanley Park Vancouver—a renowned gay cruising spot—where he accidentally found himself in the center of an organized cruising operation while shadow boxing, then discusses how being gay in 1980s Soviet Estonia meant risking your life in ways modern Western gay culture doesn't require.

Ari Matti
“I take my shirt off. It's like sunny. I got some sun on my I got a little tan going. I do a little push-ups. I do a little shadow boxing. I'm alone in the woods.”
Ari describes what he was doing in Stanley Park when he first attracted attention from cruisers
▶ 9:53
Ari Matti
“I stumble on this tree stump. You know, like a tree stump. And I Oh yeah, for sure I've seen them. 80 to a 160 amount of condoms like on the floor. Just this mass of used up condoms.”
Ari discovers evidence of the park's notorious cruising history while trying to escape
▶ 15:36
Ari Matti
“He makes eye contact with me. Why do they keep doing that? I don't know. It's crazy. He's like, "You want some?"”
Ari reflects on why multiple men kept making direct eye contact and propositioning him during the incident
▶ 17:10
Ari Matti
“A homosexual in the '80s Soviet Union, 1980s, now that's he sucked dick risking his life. Now, he loves it. He'd be loving but he loves either loves or he likes mysteries that end in”
Ari contrasts the danger faced by gay men in Soviet times versus modern acceptance in the West
▶ 23:54
Ari Matti
“So, when did you and he's like, "Man, I always knew it, but I hid it so deep in me." You know, and he was like drug addict, drinking. He was even like um he told me when he was young he was kind of violent against women cuz you know you hate yourself.”
Ari describes what his Estonian gay friend told him about suppressing his sexuality under Soviet rule
▶ 24:50
Ari Matti is a stand-up comedian from Estonia, often called the "Estonian Assassin" for his country of origin. He's appeared on Kill Tony and is currently touring across the United States. Known for his storytelling and willingness to explore edgy, provocative topics in his comedy.
1
Sexual repression under authoritarian regimes creates lifelong intensity Ari's Estonian friend, closeted during Soviet rule and forced into drugs and violence as outlets, eventually experienced liberation in Finland—but the decades of suppression fundamentally shaped his relationship to sexuality as transgressive and thrilling rather than normalized. This suggests that societal acceptance in modern gay culture may paradoxically remove the adrenaline and mystery that attracted men to risky encounters historically.
2
Public cruising culture thrives in specific parks Stanley Park in Vancouver and Schenley Park in Pittsburgh are well-known gay cruising locations with organized activity in secluded trails and wooded areas. The infrastructure—condom piles, established routes, signaling systems—suggests sustained, organized community use over time. These spaces persist despite legal risks because they fulfill a need for anonymous encounters.
3
Coming out in liberal cities offers institutional support gay men lacked historically Being gay in 1980s San Francisco versus 1980s Soviet Estonia represented an existential difference: one offered potential Netflix deals and family support, the other meant hiding sexuality so deeply it manifested as substance abuse and violence. Modern gay identity in the West is now integrated into mainstream media and entertainment, flattening it from dangerous transgression to lifestyle choice.