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Film credit

Jake Gyllenhaal

Also referred to as Gyllenhaal, gillenhall

Stats

Episodes featuring their films
4
Movies in this archive
4

Rewatchables episodes featuring Jake Gyllenhaal’s films

Zodiac

2007 film

Bill Simmons · Chris Ryan · Sean Fennessey

Aired January 26, 2026

City Slickers

1991 film

Bill Simmons · Chris Ryan · Sean Fennessey

Aired June 15, 2021

Zodiac

2007 film

Sean Fennessey · Chris Ryan · Andy Greenwald

Aired December 14, 2017

Displaying all 4 episodes

Mentioned in discussions

Zodiac The Rewatchables
Zodiac

Apex Mountain

David Fincher (creative apex disputed); Mark Ruffalo as a movie detective; John Carroll Lynch; Zodiac within Fincher’s filmography

In the discussion (10)
Approx. transcript time · 02:17:56Read transcript
Zodiac The Rewatchables
Zodiac

Casting What-Ifs

Gary Oldman, Orlando Bloom, Brad Pitt, and Jennifer Aniston appear in a detailed casting history.

In the discussion (6)
Approx. transcript time · 02:07:46Read transcript
Zodiac The Rewatchables
Zodiac

What’s Aged the Worst?

The abrupt four-year title card, too little Downey–Gyllenhaal time, their fictionalized friendship, Anthony Edwards’s wig, and the film’s persuasive Arthur Leigh Allen framing

In the discussion (5)
Approx. transcript time · 01:56:40Read transcript
Zodiac The Rewatchables
Zodiac

The David Fincher Award for “Wow, This Director May Have Been a Fucking Lunatic”

Digitally adding knuckle hair to Jake Gyllenhaal’s hands

The panel proposes a new category here.

In the discussion (3)
Approx. transcript time · 01:49:06Read transcript
Zodiac The Rewatchables
Zodiac

What’s Aged the Best?

True-crime culture, period San Francisco, Downey, the protagonist shift, Graysmith’s internet-like obsession, Fincher’s catalog, and several craft details

In the discussion (14)
Approx. transcript time · 01:35:45Read transcript
  • Chloë Sevigny’s humor and deliberately ordinary styling are praised.
  • The rise of true-crime culture gives the film more resonance. — Bill Simmons
  • Late-1960s and early-1970s San Francisco is nominated as an enduring setting. — Bill Simmons
  • Fincher’s San Francisco feels haunted and geographically unmistakable.
  • Downey’s mutterings and banter with Gyllenhaal are praised. — Chris Ryan
  • The tonal and procedural shift from Toschi to the isolated Graysmith is praised. — Chris Ryan
  • The unsolvability of mundane tragedy is treated as a lasting subject. — Sean Fennessey
  • Graysmith’s external obsession anticipates internet behavior. — Sean Fennessey
  • Robert Downey Jr.’s comeback context is nominated. — Bill Simmons
  • Zodiac’s place in Fincher’s catalog is nominated. — Bill Simmons
  • Paul Avery’s waterside home is praised.
  • The Chronicle newsroom recreation is praised for capturing an empty morning newspaper office. — Bill Simmons
  • The soundtrack’s gradual move into yacht rock is praised. — Bill Simmons
  • Downey’s on-screen smoking is praised.
Zodiac The Rewatchables
Zodiac

Steven Seagal shitting on himself award for most unbelievable anecdote from the actual film shoot

Fincher’s repeated takes and exacting treatment of Gyllenhaal, Downey, and Ruffalo supply several production-shoot anecdotes.

In the discussion (6)
Approx. transcript time · 01:29:09Read transcript
Zodiac The Rewatchables
In the discussion (15)
Approx. transcript time · 01:12:36Read transcript
  • The Lovers Lane opening murder and its flashlight-on-gun image are nominated. — Bill Simmons
  • The Vallejo fireworks opening is nominated. — Bill Simmons
  • Graysmith reading the decoded letter as Paul Avery watches is nominated. — Bill Simmons
  • The Lake Berryessa bluff murder is called one of the most unsettling murder scenes.
  • Melvin Belli’s live television appearance is nominated.
  • The Ione Skye car sequence is nominated. — Bill Simmons
  • Downey and Gyllenhaal’s newsroom and bar exchanges are nominated.
  • The Arthur Leigh Allen interrogation is the final favorite. — Bill Simmons
  • The search of Allen’s trailer is nominated. — Bill Simmons
  • The basement sequence is nominated, though one host says repeat viewings reduce its impact.
  • Graysmith’s late-night visit to Toschi is nominated. — Bill Simmons
  • The Ace Hardware stare-down is nominated.
  • Toschi and Armstrong processing the taxi-cab murder scene is nominated. — Chris Ryan
  • Graysmith and Toschi’s first meeting is nominated. — Sean Fennessey
  • The final Door-to-Door breakfast is called a favorite except for the interrogation. — Sean Fennessey
Brokeback Mountain

Apex Mountain

Ledger’s living-career peak and Lee’s creative freedom: yes

In the discussion (3)
Approx. transcript time · 01:59:27Read transcript
  • Ledger’s living-career apex and Lee’s creative freedom are placed here; Gyllenhaal’s comes later around End of Watch and Prisoners. — Bill Simmons
  • Williams and Hathaway are rejected; traumatized Williams wives peak in Manchester, and a sheep-film counterexample is favored. — Wesley Morris
  • Gay Westerns qualify, while Power of the Dog does not work for either participant. — Wesley Morris
In the discussion (2)
Approx. transcript time · 01:23:37Read transcript
  • De Niro in Goodfellas is the unique10 benchmark, Cole Hauser’s Goodwill Hunt entrance about9.7, and Ledger9.5 for convincing cigarette handling. — Bill Simmons
  • Gyllenhaal is around7.5 to8, including the shared postcoital smoking; Cruise, Roberts and Reeves in Hardball are unconvincing comparisons. — Bill Simmons
Brokeback Mountain

Most Rewatchable Scene

The quit-you confrontation and opening

In the discussion (10)
Approx. transcript time · 00:59:01Read transcript
  • The opening glances and famous tent scene are nominated. — Bill Simmons
  • A first-time young viewer’s surprise at the tent scene becomes tears by the ending. — Bill Simmons
  • The fight and goodbye, Ennis’s wall punch and the later refusal of another job are highlighted. — Bill Simmons
  • Lorraine’s arrival and Jack’s reunion visit after the postcard are nominated. — Bill Simmons
  • The reunion kiss and Alma discovering it expose the relationship through an outsider’s view; the loss of control is both moving and risky. — Wesley Morris
  • The campfire tire-iron story establishes mortal stakes; the two Thanksgivings contrast father-in-law conflict with Alma revealing she knew about the fishing lie. — Bill Simmons
  • The double date and cabin invitation are a favorite, with the invitation becoming a personal running joke. — Bill Simmons
  • The quit-you confrontation is called the best scene; Ledger collapses and Gyllenhaal registers that he pushed too far. — Wesley Morris
  • The ambiguous call to Lorraine and the parents’ house with the hidden shirts are praised. — Bill Simmons
  • The opening is the other final favorite, praised as a modern dance between the men. — Bill Simmons
The Gambler The Rewatchables
In the discussion (7)
Approx. transcript time · 00:07:48Read transcript
The Blair Witch Project

Recasting Couch

Recognizable young stars considered, then challenged

In the discussion (2)
Approx. transcript time · 01:07:00Read transcript
Displaying discussions 1 - 12 of 28 in total

Films in the archive