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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

The Pelican Brief

Recasting Couch

Zendaya; gender-swap with Holland; Gyllenhaal/Driver; Davidson disputed; Goldwyn as president

In the discussion (4)
Approx. transcript time · 01:17:03Read transcript
  • Zendaya is proposed for Darby; a gender-swapped version would pair her reporter with Tom Holland’s law student.
  • Jake Gyllenhaal and Adam Driver are considered for Gray.
  • Pete Davidson is proposed for Gray but receives immediate resistance.
  • Goldwyn could return as the president.
City Slickers

Sequel, Prequel, Limited Series, or All-Black Remake

10-episode Netflix series with grown-up Danny taking his aging father on a cattle drive

In the discussion (3)
Approx. transcript time · 01:10:28Read transcript
  • The pitch: Jake Gyllenhaal's character is now his dad's age, Mitch has divorced and moved West, and Danny takes a 30-year-anniversary cattle drive to reconnect with his aging father.
  • A twist has Gyllenhaal back as Detective Loki investigating Kirby's murder; another floats a Brokeback Mountain twist with Curly Jr. — Chris Ryan
  • Crystal and Stern would be de-aged like The Irishman, and Lovitz would return doing Godfather 3 this time.
City Slickers

Half-Assed Internet Research

Fantasy-vacation TV origin; plot borrowed from The Cowboys; Jake Gyllenhaal's debut; the true best-day story; 10 or 11 Normans; river-crossing trouble; Lindsay Crystal as Mitch's daughter

In the discussion (5)
Approx. transcript time · 01:02:11Read transcript
  • Crystal got the idea from a TV show about middle-aged men on life-changing fantasy vacations, borrowed the plot from John Wayne's The Cowboys, and hired Lowell and Babaloo.
  • Ten-year-old Jake made his film debut as Crystal's son, and a Crystal quote about him always performing and singing South Pacific is read and questioned. — Chris Ryan
  • Kirby's horse allergy is repeated, defended as half-assed internet research. — Chris Ryan
  • Crystal's best-day story really happened, 10 or 11 cows played Norman, and Norman's birth scene was shot in three states.
  • The river crossing was the toughest to shoot because the cows kept mounting each other, and Mitch's daughter was Crystal's real daughter Lindsay, called the best casting ever.
City Slickers

What’s Aged the Best?

Midlife-crisis angle; Curly's shocking death; young Jake Gyllenhaal; Palance's one-armed pushups; the title spoken in dialogue; Crystal's one-liners; the classroom life-stages monologue; normal people in a Western setting; the supporting cast

In the discussion (10)
Approx. transcript time · 00:39:20Read transcript
  • The midlife-crisis angle actually works, and Curly's death is still shocking on repeat viewings and well handled.
  • Young Jake Gyllenhaal has aged great and looks pretty similar now. — Bill Simmons
  • Palance's one-armed pushups became one of the five most famous Oscars moments, recreated the next year when he dragged out a giant Oscar statuette. — Bill Simmons
  • Saying the title in the dialogue ('you city slickers') is appreciated, along with fortune-cookie one-liners such as 'at this age, you are who you are.'
  • The idea that at a certain age you are who you are is rejected in two replies; 39 is not a peak, and CR is joked to be running an NBA team in ten years.
  • Crystal was 43 during the making, looks 51, and plays a character turning 39; men in older movies like Mikey and Nicky looked far older than their ages. — Bill Simmons
  • Crystal's terrible one-liners are enjoyed, such as women needing a reason to have sex and men a place; he is said to have written them, sneaking in Tonight Show material.
  • Mitch's classroom monologue on life by decade is played and called really good script writing.
  • Normal people in a Western setting, a fish-out-of-water tale, works well, and the surrounding cast is well cast and fun to be around.
  • One potential item is held back as a probably unanswerable question.
City Slickers

Most Rewatchable Scene

Best Day, Worst Day scene; plane ride home from running with the bulls; Nancy confronting Phil at the party

In the discussion (11)
Approx. transcript time · 00:27:04Read transcript
  • The plane ride back from running with the bulls is a favorite: Mitch's sore-rear dad jokes, Ed being told he'll soon be dating sperm, Phil pretending to sleep, and the question of when it will ever be enough. — Bill Simmons
  • The Crystal-Tambor office scene is called weird, but the pizza ad is perfect, and the 'as good as you're ever going to look' line sets up the movie.
  • The school scene with the guy from Total Recall is called crushing it, and it marks Jake Gyllenhaal's debut with a spiked haircut. — Chris Ryan
  • The fireplace scene where Kirby and Stern fight is nominated.
  • The harmonica scene between Jack and Billy is quoted and all their scenes together are praised. — Bill Simmons
  • Curly's 'one thing' secret-of-life scene is quoted.
  • Best Day, Worst Day is called 'my favorite, most rewatchable... the best scene,' with the story of standing up to his father quoted.
  • Mitch's description of first walking into Yankee Stadium after seeing it on black-and-white TV is called pretty awesome, but his being a Mets fan is flagged as the number one nit. — Bill Simmons
  • One answer says the movie falls apart in the last 40 minutes with no rewatchable scenes there, and picks Nancy the cashier confronting Phil about her pregnancy at the party. — Sean Fennessey
  • Best Day, Worst Day is the pick, and Kirby is phenomenal in that scene. — Sean Fennessey
  • Underwood's staging of the stampede is floated as most rewatchable; the reply grants parts are beautiful but calls it a flat-looking Western with a good script and great bones, likened to Raiders.
In the discussion (5)
Approx. transcript time · 01:19:03Read transcript
  • The hosts report that Britney Murphy was originally lined up to play Mary, taken to be the Anna Pacoan role, and it fell through; she might have fit Rosario Dawson's role instead. — Bill Simmons
  • The hosts report that Toby McGuire bought the rights to the novel and was supposed to star, then chose Spider-Man and stayed on as a producer. — Bill Simmons
  • The movie is judged not as good with McGuire as Monty, though he is called a dark horse who can surprise. — Wesley Morris
  • Favorite McGuire performances named include Brothers with Jake Gyllenhaal, Spider-Man 2 for its reaction shots in action scenes, and the first 40 minutes of Spider-Man 3; Ice Storm is called his best movie. — Wesley Morris
  • The Ice Storm is described by a host as one of the great movies about whiteness made by a non-white filmmaker, with James Shamish writing and Engley directing; a future Ice Storm episode is promised. — Wesley Morris
In the discussion (4)
Approx. transcript time · 01:00:56Read transcript
Zodiac The Rewatchables
In the discussion (6)
Approx. transcript time · 00:56:11Read transcript
  • The field is framed as basically Downey, Fincher and Gyllenhaal, though Sean's case for Ruffalo is called pretty convincing; a hedge is offered as suitable for a film that gives no easy answer, and artistically Fincher is expected to be remembered for this as his most interesting film to date.
  • The case for Downey: he comes into the film and leaves two-thirds of the way through with perhaps one last glimpse, gets no hero moment or coda where filmmakers less concerned with ambiguity would have given him one, goes from liking a tipple or two to being taken over by it, and still has the majority of the quoted lines; the award is given to Downey.
  • A dissent is less mesmerized by the Downey performance and goes with Ruffalo, pointing to how the case degraded the people involved, Avery a hotshot at the top and clutching an oxygen tank by the end, and to the scene where Graysmith reintroduces himself to Inspector Toski (as transcribed) after they met at the movie premiere and gets, after a beat, 'I'm sure it was magical', a very dry, unimpressed cop moment.
  • Ruffalo never has the 50-home-run seasons of a Downey and never goes for it, which is the hallmark of what makes him mesmerizing and rewards rewatching; Downey's shtick has to some degree aged badly when seen through the filter of Tony Stark, The Judge and Due Date, though there is more gravity and weight here, so recency bias may make it harder for some to slide into the performance.
  • Fincher is also named as the winner, for the level of scholarship and depth of understanding of the world on display: despite scenes feeling samey, the narrative geography always locates you relative to the paper; his films are read as wars between filmmaker and actor, less successful when the actors gave up, and it is fascinating to watch him do battle with Affleck in Gone Girl or Eisenberg in Social Network, with Downey and Eisenberg seeming born for these films; Gyllenhaal is paraphrased as saying Downey has fifty ideas in a scene where most actors have five, so take 88 has a new idea just like take three, the 'Jesus Christ on crutches' line was probably improvised, and without Downey the film would be a little flat.
  • A joke names Kevin Feige as one more big winner for getting to see two-sevenths of the Avengers on screen together, so the film invents modern television, the MCU and, thanks to Chloe Sevigny, Bloodline.
Podcast choices
Speaker not identified
Robert Downey Jr.
Speaker not identified
Mark Ruffalo
Zodiac The Rewatchables
In the discussion (8)
Approx. transcript time · 00:47:18Read transcript
  • Before the nominees, a moment in the credits is called possibly the best in the film: after Gyllenhaal, Ruffalo and Downey, the names Brian Cox, John Carol Lynch, Elias Codius, Dermot Malroney and Donal Loge (as transcribed) appear, a that-guy all-star team; Malroney as Captain Marty Lee is loved and Cox as Melvin Belli really makes the most of his moment.
  • More favorites: Philip Baker Hall as Sherwood, the handwriting specialist who starts drinking a little; Clea Duvall, with a great heat-check scene; John Goetz (as transcribed), from Blood Simple, as the Chronicle editor; and Anthony Edwards, fantastic and unexpected.
  • One pick gives the award specifically to Cox, with the Melvin Belli phone-call clip played, 'Is there something I can call you that's a little less ominous?', for making the most of his few moments, the television interview, the sincere attempt to offer the caller a lifeline, and the way he physically takes the incredible screaming sound.
  • Jimmy Simpson (as transcribed), who plays the shooting victim at the start and returns at the end, prompts a detail: the character is Mike Mageau, and when the name is reported over the Vallejo PD wire it is said aloud in the newsroom as 'Mayhew', so the film intentionally misleads in a way that was probably true to how it was said, an obsessive Fincherism; James LeGroix (as transcribed) is good and weird, and Zach Granier (as transcribed), the boss in Fight Club, runs the Vallejo police department.
  • A second pick is Elias Codius (as transcribed) as Detective Mullinax (as transcribed), a great real name: a that-guy who can shoot when given the ball, known to the hosts' generation as Casey from Teenage Mutant Ninja Turtles, a guy who looks like a cop and rarely gets a stage this large, and a great serial killer in Fallen with Denzel Washington, directed by Gregory Hoblitz (as transcribed).
  • Asked directly for a winner, a third pick is John Carroll Lynch as Arthur Lee Allen, with the 'Nobody calls me Arthur' clip: the role basically made the second half of his career, he directed the last film starring Harry Dean Stan (as transcribed) this year, and he is a well-known theater actor remembered as Norm in bed with Francis McNormand (as transcribed) at the end of Fargo.
  • Asked whether the film still works with a huge star like Anthony Hopkins as Arthur, the answer is not as well: it has to be a face whose physical presence unsettles because you feel you could have seen him without knowing why, since viewers bring previous films into the room and would read a famous actor as an important part; the misdirect succeeds because the only place to remember Lynch is Fargo, where Norm is a completely different, friendly disposition.
  • Later, the Ioni Sky (as transcribed) roadside scene is called another Dion Waiters performance and the hardest scene for one host to watch.
Zodiac The Rewatchables
Zodiac

Casting What-Ifs

Gary Oldman was to play Melvin Belli but was judged not heavy enough; Jennifer Aniston recommended Mark Ruffalo to Fincher; Andrew Garfield as a later Graysmith; Anthony Hopkins as Arthur Leigh Allen

In the discussion (4)
Approx. transcript time · 00:47:18Read transcript
  • The only casting what-if with any internet leftovers is Melvin Belli: Gary Oldman was supposed to play the role, and Fincher passed because he lacked the girth to play Belli, which lands oddly now that Oldman is playing Winston Churchill in all his girth in Darkest Hour; the hosts ask why a director who can add blood splatter could not add a few pounds, doubt anyone cares whether Belli weighed 250 or 175, and joke that human body fat is as sacred to Fincher as oak trees.
  • Ruffalo was recommended to Fincher by Jennifer Aniston, and Fincher had liked him in Collateral.
  • A side question asks whether Andrew Garfield, a little more of a boy scout, would have been a better Graysmith had the film been made five years later; Eisenberg is floated and rejected, and Gyllenhaal is called alarmingly handsome despite the wide-eyed look, as is Garfield.
  • Asked whether the film still works with a huge star like Anthony Hopkins as Arthur, the answer is not as well: it has to be a face whose physical presence unsettles because you feel you could have seen him without knowing why, since viewers bring previous films into the room and would read a famous actor as an important part, and the only place to remember Lynch is Fargo, where Norm is a completely different, friendly disposition.
Zodiac The Rewatchables
Zodiac

Apex Mountain

Robert Downey Jr. (Fincher: greatest accomplishment but not his best movie, 130)

In the discussion (8)
Approx. transcript time · 00:40:24Read transcript
  • For Gyllenhaal this is definitely not Apex Mountain; Enemy is offered, an incredible performance even though twin movies are usually bad and that one is triply complex, and Prisoners, with Detective Loki a series of choices; the things disliked in his early performances have become something he steered into, he works hard and made himself a better and more interesting actor, going from hiding the seams to embracing them, with this film perhaps the bridge.
  • A joke nominates Source Code; otherwise everything after this is found better: Stronger, which came and went this year, is a really difficult performance in a familiar story that did not get the praise it was due, and he is consistently excellent now, so despite the affectations this is a great turning point.
  • The case that this is Downey's Apex Mountain: people who know him only as a global superstar and brand in the last decade don't know the golden child who couldn't get it done, spoken of in hushed tones as the most talented actor of his generation yet undone by demons and addictions until a turning point around 2004 to 2006; Fincher caught him off Kiss Kiss Bang Bang, another one high on the list, and this film marries the electric comet-in-the-sky quality with a gravity that was sluiced away as he became more of a comic-book figure; Good Night and Good Luck was solid and controlled, but nothing around this suggested he could put together so mannered a performance.
  • Downey's 80s run is called underrated, with Less Than Zero and The Pickup Artist, and his late-90s slide read as a tragedy because he had been consistently fascinating when used correctly, as in Soap Dish (as transcribed) and Wonder Boys, a film ready to be rediscovered; weighing the larger success arc, this fits perfectly as Apex Mountain for one host, with the global franchise-head apex coming a year later.
  • Ruffalo is the biggest takeaway of the rewatch and perfectly cast: the Dave Toski (as transcribed) myth, the real cop who was Bullitt and partly the basis of Dirty Harry and perhaps the most recreated real-life cop ever, is played far more subtly than in the other Zodiac films, with the voice and accent right on, the floppy bow tie, pants and trench coat, and a softness that is a radical choice for a superstar murder police who literally asks about due process and is shown to be a grunt doing phone work.
  • The vulnerable moment when Toski (as transcribed) is accused of writing the last Zodiac letter and gets a call at his house from Graysmith is loved: his wife, played by June Diane Raphael, is outraged on the phone, and Ruffalo delicately takes the phone from her, hangs it up and walks away without a word, jazz playing, in a bathrobe; but it is not his Apex Mountain, since You Can Count On Me is hard to top as where many first saw him.
  • Collateral is still a thing for some among Ruffalo's cop performances; he was recommended to Fincher by Jennifer Aniston, who had liked him in Rumor Has It, the quasi-sequel to The Graduate, and Fincher liked him in Collateral.
  • Asked whether this is Fincher's Apex Mountain, the answer is that it is his greatest accomplishment but not his best movie: Fight Club and Seven are iconic and stitched into people's lives, The Social Network is his best and the one liked most, but Zodiac clearly took the most to achieve, is his most personal and therefore most interesting film, though it will never be as beloved.
Displaying discussions 13 - 24 of 28 in total

Films in the archive