The Rewatchables
Friday, June 5, 2026A Rewatchables Summer Mailbag!
Bill Simmons, Chris Ryan, and producer Craig Horlbeck riff through listener mailbag questions proposing new Rewatchables award categories, debating city "Apex Mountains," and reminiscing about the Ringer's early days.
Key takeaways
- New category proposals dominate the episode: a "Danny McBride Best Character Entrance Award," a "Dion Waiters Plus" tier for near-rename-worthy performances, a "Playing Yourself" category (Keanu in Always Be My Maybe, Malkovich in Being John Malkovich), and a "Sharon Stone Going Going Gone" award for the moment a movie asks you to suspend all disbelief.
- "Apex Mountain" for cities sparked debate — which year was each city at its cultural/sports peak? Boston 2004 and Seattle 1993 got easy agreement; San Francisco 2016 did not (consensus leaned late '70s or mid-'90s).
- Peter Stormare may have the strangest actor résumé in history: woodchippered Steve Buscemi, eaten by dinosaur, ear bitten off by John Goodman, swapped Tom Cruise's eyeballs, directed snuff films, helped George Costanza preserve his Frogger high score.
- The Sasha Jensen correction: The award for "why didn't this actor become a bigger star?" has been called the "Sasha Jenkins Award" for years — the actor's actual name is Sasha Jensen. They debated keeping the wrong name because it proves the point.
- The Ringer's 10-year anniversary prompted reflection: 2016 was one of the wildest years in sports history (Warriors' 73-win collapse, Cubs World Series, KD to Golden State, Cavaliers comeback), and Simmons revealed he spent months thinking he was having a breakdown — it turned out his contact lenses were too strong after his prescription improved in his mid-40s.
People, organizations, products, and links mentioned
- Bill Simmons, Chris Ryan, Craig Horlbeck — hosts/producer
- Peter Stormare — actor with the praised résumé (Fargo, Armageddon, Mission: Impossible 2, 8mm, Seinfeld)
- Michael Madsen — compared unfavorably to Stormare
- Alec Baldwin in Glengarry Glen Ross — cited as possible all-time Dion Waiters performance
- Phil Michael Thomas (Tubbs on Miami Vice) — discussed re: why he didn't become a bigger star
- Daniel Day-Lewis — compared (controversially) to James Harden; never won Best Picture
- Sharon Stone — claimed to have hit a home run at Dodger Stadium during a Simmons interview
- Diane Keaton / Kay Adams in The Godfather — Simmons doubles down on "bad character" take
- Sasha Jensen (Dazed and Confused) — the award has had the wrong name for years
- FanDuel Predicts — sponsor
- The Ringer — celebrating ~10 years
- Against All Odds (1984) — flagged as a proto-There's Something About Mary
- Miami Vice Season 1 — discussed as a summer rewatch; starter kit episodes named: two-part pilot, Calderon's Revenge, Golden Triangle, Glades, the Bruce Willis domestic-violence arms dealer episode, Milk Run, Smuggler's Blues
Notable moments
- On Peter Stormare: "He's woodchippering people to death. He's directing snuff films. He's replacing eyeballs... Cruise is just the best at everything he does. Best bartender, best pilot, best spy."
- On the Sasha Jensen revelation: "We've been saying the wrong name the entire time." — "I think we keep it. It's funnier that it's Sasha Jenkins."
- On the Dan McBride entrance category — Reggie Hammond singing the Police in 48 Hrs., Todd Parker's zoom-in entrance in Boogie Nights, and Lester Bangs doing Iggy Pop in Almost Famous were the standout nominees.
- Simmons's eyesight story: he spent months thinking he had a brain tumor while launching the Ringer and doing his HBO show; it was just his contacts being too strong after his prescription improved.
Time saved
Runtime is listed as unknown, but based on transcript density (~54 minutes of content), this summary saves you roughly 50 minutes of listening.