It all started one day in late May, when I finally watched “Brokeback Mountain,” the 2005 romantic drama starring Jake Gyllenhaal and Heath Ledger.
I didn’t think much of my decision until two days later, when I was mindlessly scrolling through Instagram and came across clips from the 2014 thriller “Nightcrawler.” I had been meaning to watch that one for a while, too, so I took a chance and decided to view it that very night.
“Brokeback Mountain” and “Nightcrawler” have one thing in common: Jewish actor Jake Gyllenhaal.
After finishing “Nightcrawler,” I made an impulsive decision: I would watch all of Jake Gyllenhaal’s movies. Soon his famous phrase “I wish I knew how to quit you” began to define my relationship with Jake Gyllenhaal and his films, as I went through all 40 movies he’s credited as an actor on in his IMDB. It took me over a month to finish all of them — and to drive everyone in my life wild with how much I talked about Jake Gyllenhaal.
But I had a purpose. Without further ado, I present to you all 40 of Jake Gyllenhaal’s movies, ranked:
40. “Josh and S.A.M” (1993)
To say that this movie is bad is an understatement. “Josh and S.A.M” is about two brothers, the titular Josh and Sam. The plot is, loosely, that older brother Josh (Jacob Tierney) finds out his mother is getting remarried, his father calls him “weak,” and so he decides to lie to his younger brother Sam (Noah Fleiss), telling him he is actually a “Strategically Altered Mutant” who is being used as a soldier by the Pentagon to fight a war in Africa. If you’re confused, so was I. This film also features a creepy relationship between a 12-year-old boy and a 16-year-old girl, plus the most Westchester tri-state area accent one will ever hear by a 7-year-old. It feels very underdeveloped, with few stakes to keep one invested.
39. “Jiminy Glick in Lalawood” (2004)
When I said I’d watch all of the movies Jake Gyllenhaal is featured in, I meant all of them — including the ones where he has a one-second cameo as himself. “Jiminy Glick in Lalawood” stars Martin Short as the titular Hollywood movie critic who attends the Toronto International Film Festival and wreaks havoc upon everyone. It features Linda Cardellini (Jake Gyllenhaal’s co-star a year later in “Brokeback Mountain”), Janeane Garofalo, John Michael Higgins, Jan Hooks and Elizabeth Perkins in starring roles in a movie that is both incredibly offensive (fatphobia, racism and homophobia take center stage for most of the film) and completely without a plot or a point. The funniest part of this movie is Martin Short’s impression of David Lynch, but even that feels completely random and without a real purpose.
38. “Accidental Love” (2015)
In order to understand where “Accidental Love” is coming from, you have to understand that it barely got made. Production shutdowns, budget issues and cast walk-offs prompted the film to be released seven years after it was initially shot. Directed by Stephen Greene (aka David O. Russell — he wanted nothing to do with the movie) and adapted from a play by Kristen Gore (yep, Al Gore’s daughter; her brother Al Gore III is also in this), “Accidental Love” follows Alice Eckle (Jessica Biel), a woman whose life is turned upside down when a nail gun is accidentally shot into her head. Learning that she has no health insurance, the doctors refuse to give her brain surgery. From there, Alice goes on a mission to fix the healthcare system for those who have strange medical conditions but are unable to afford help. Jake Gyllenhaal stars as Rep. Howard Birdwell, her congressman who takes up her cause in congress and eventually falls in love with her. This film is rife with racism and homophobia and feels like it was written by a bunch of children doing improv. The characters feel very underdeveloped without stereotypes and each scene feels very disconnected from the purpose of the movie (which I’m still unsure of). Do yourself a favor and skip this one, but if you’re interested, this scene has Jake showcasing an acting technique I’ve coined as “Kooky Jake.”
37. “A Dangerous Woman” (1993)
Before Jake Gyllenhaal was known as an Academy Award-nominee and an MTV best kiss winner, he was merely director Stephen Gyllenhaal and screenwriter Naomi Foner’s child. Much of Jake’s early work had him and sister Maggie Gyllenhaal starring in their movies together. (Ah, nepotism.) Credited as “Jacob,” Jake’s second film role, therefore, has him for a few minutes as an annoying 12-year-old on his bike in the complicated and dull drama that is “A Dangerous Woman.” It’s not worth getting into — the film is confusing, slow and underdeveloped, with very little going on. It isn’t until the very end that things start to heat up —but by then you’ll be fast asleep.
36. “Homegrown” (1998)
Yet another one of Stephen Gyllenhaal’s films that features Maggie and Jake in small roles. Starring Billy Bob Thornton, Hank Azaria (alumni of the Jewish camp I worked at) and Ryan Phillipe, “Homegrown” is about three California weed farmers who must take control of the supply once their boss is killed. The pacing of the film is very fast but incredibly confusing. Jake is in the film for about two seconds as he staggers into the frame as the son of (his real-life godmother) Jamie Lee Curtis — in a fun change, he has bleach blonde hair. There are lots of missed opportunities for character development, yet for the feeling of weed-induced paranoia the film tries to evoke, it succeeds.
35. “Lovely and Amazing” (2001)
For a film with that title, you’d expect better. Or at least I did, but I was sorely disappointed. The film is about a mother and her three daughters who are all incredibly narcissistic and insecure. As someone who completely understands what the women are going through with regards to body image and appearance, I found myself turned off. Jake plays Jordan, a 17-year-old who runs a one-hour photo and crushes on his narcissistic and married employee Michelle Marks (Catherine Keener). He’s giddy and full of life in a movie about miserable people that crave validation from others. This film is filled with lots of fatphobia – be wary.
34. “Bubble Boy” (2001)
This wins the title for the most quarantine/pandemic Jake Gyllenhaal movie. “Bubble Boy” is one of the most chaotic movies I’ve ever seen. Based on the 1976 TV movie “The Boy in the Plastic Bubble,” “Bubble Boy” has Jake Gyllenhaal as the titular character born without an immune system who decides to venture outside in a plastic bubble suit to go after the girl he loves and stop her wedding. It’s one hell of a ride that I don’t recommend being sober for. Jake goes everywhere in this one; he gets picked up by a cult, heads to Las Vegas via motorcycle by Danny Trejo, and even flies. It’s a very bizarre but fun mess — though a bit problematic and filled with lots of racism, xenophobia, antisemitism and ableism. The characters aren’t developed well beyond lots of stereotypes, but Jake shines as a silly teenager that tries to follow his dreams despite adversity (being stuck in a bubble).
33. “Spirit: Untamed” (2021)
I went to see the animated children’s movie “Spirit: Untamed” opening weekend alone, without a child and as the only young adult. It felt weird. Based on the Netflix show “Spirit Riding Free” (which I had not seen), “Spirit: Untamed” is about Lucky, a young girl who returns to the city to live with her father (Jake Gyllenhaal) for the first time since her horseback-riding mother’s passing. There, Lucky connects with a wild horse named Spirit who teaches her about friendship and family. I’ll be honest, there were times when I almost cried, as the bond between Lucky and Spirit was very cute. However, the film fails for a variety of reasons; the script is awkward at times and the pacing feels a bit fast (it’s a children’s movie so I can understand that). Jake’s voice is a lot to take in, as it’s extremely high-pitched and nearly unrecognizable (he does sing, so the ticket was worth it). “Spirit: Untamed” does its best with what it has, which isn’t a lot.
32. “Prince of Persia: The Sands of Time” (2010)
We’ve made it to 2010 Jake Gyllenhaal, which was his “heartthrob Jake” year. From People Magazine’s sexiest man alive (the cover star may have been future co-star Ryan Reynolds, but a small image of Jake appears in the left hand side along with Brad Pitt) to showing off his carefully chiseled physique and sex appeal (and weirdly, a lot of scarves) in two movies, this was the year when Jake’s charm — and good looks — shined through. (I’ve theorized that was the year Taylor Swift started crushing on him, using her Disney connections from being in 2009’s “Hannah Montana: The Movie”to contact him. They dated later that year.)
As his first action movie, “Prince of Persia” is a lot to take in — it’s rife with cultural appropriation, white washing and a terrible British accent by Jake himself. The plot is rather complicated to explain, but all you need to know is it finds Jake Gyllenhaal as Prince Dastan, who, after his father is killed, goes on a mission to prove his innocence and obtain the trust of his brothers once again. Along the way, he discovers a magical dagger containing sand that can turn back time. There are a ton of clichés, featuring lines like “the promise must not be broken” and “we haven’t enough time.” There is some sexual tension, but that doesn’t make up for the fact that “Prince of Persia: Sands of Time” does not make much sense. Still, it’s entertaining to watch Jake do parkour and sword fight.
31. “Love and Other Drugs” (2010)
This followed “Prince of Persia” in 2010 (the year of “heartthrob Jake”). It’s one of Jake’s most well-known movies and his first time taking a stab at the rom-com genre, but it does not break into the top 30 Jake Gyllenhaal film canon, in my opinion. Starring Jake alongside Hank Azaria, Josh Gad, and Anne Hathaway, “Love and Other Drugs” has Gyllenhaal as Jamie, a Pfizer salesman in the 1990s who falls in love with a woman with Parkinson’s. (Sidenote: This felt like a very relevant film for how present Pfizer is currently, with the training program showcasing several hilarious visuals including fireworks as the brand logo is displayed. As a member of the #pfizergang, I felt incredibly connected to this movie.)
As a comedy, this film definitely showcases Jake’s range. However, the plot pacing feels off at times and the directors didn’t do the best job setting the tone for Jamie being a womanizer or showcasing his motivations for being a Pfizer sales rep. The love story between Jamie and Maggie is cute, but I wish we had gotten a chance to see more of her alone instead of just through his perspective — it feels like Maggie is just his “manic pixie dream girl” whom he suddenly has the urge to care and change for. Still, the film is enjoyable, and hilarity ensues whenever Josh Gad is onscreen.
30. “Velvet Buzzsaw” (2019)
Art has the power to transform, to evoke emotion, to present different perspectives. But according to this movie, art also has the power to kill and literally move people. Jake plays art critic Morf Vandewalt who begins to become suspicious when a dead artist’s paintings start to haunt him and the people within his circle. This horror film is very campy, exposing the elitism of the art world and the particulars of selling art and displaying it in galleries and museums. I had trouble understanding what was going on at points, and became bored with storylines, but the film speaks deeply about capitalism and art in interesting ways.
29. “Proof” (2005)
“Proof” stars Gwyneth Paltrow as Claire, a math whiz, who fears she may be going insane and following in the footsteps of her recently deceased father and mathematician Robert (Anthony Hopkins). When his former graduate student Hal (Jake Gyllenhaal) discovers a notebook that contains a mathematic proof, Claire claims it’s her work, but he is skeptical, requiring more proof that it’s hers. Soon the proof isn’t just math, but evidence of Claire’s sanity. This film operates through flashbacks and montages, moving back and forth to the past and present. It’s not the strongest of Jake’s films, but certainly tells a story that feels simple and interesting enough to follow for the viewer. As an adaptation of a play, the film does a good job using the setting to its advantage. “Proof” also introduces us to his acting method of the “Gyllenhaal giddiness” (a term I’ve coined, referencing a specific drive and determination that can be found when it comes to solving a mystery or working to achieve a goal).
28. “Demolition” (2015)
Starring Chris Cooper (three-time Jake co-star) along with Naomi Watts and Judah Lewis, Jake Gyllenhaal plays Davis, an investment banker whose wife is killed by an incoming vehicle. Through advice from his father-in-law, Davis decides to break down and “demolish” his life (physically) in order to put it back together again. In his journey to feel something and handle his emotions, Davis befriends a customer service representative for a vending machine company and her teenage son. This film uses a lot of voice-overs, flashbacks and montages in a very indie-art house way. I found myself sort of confused by the direction of where the film was going, but ultimately it’s very sweet, particularly the relationship between the teenage son and Davis (it’s also a nice change of pace to watch a platonic friendship between a woman and a man, even though he acts like she’s his mother half the time). For an exploration of grief and how it impacts men and toxic masculinity, this film is really enlightening. “Demolition” also takes place in Westchester, New York, and Davis is seen repeatedly taking the train into Manhattan – for those people that live “just an hour outside of the city,” this film sees you.
27. “The Sisters Brothers” (2018)
“The Sisters Brothers” is set in 1851 and follows the titular brothers Eli (John C. Reilly) and Charlie (Joaquin Phoenix), gunfighters hired to search and kill a man (Riz Ahmed) who has the chemical formula for finding gold. Jake Gyllenhaal plays a private detective, initially working with the brothers to capture the man before eventually freeing him and joining him on his journey to create a utopian society. For a western, the dynamic between the brothers, as well as Riz and Jake, prove very interesting to watch — there is something about the western that makes it the ultimate buddy movie (and arguably, Jake’s main genre). I found it to be somewhat of a sleeper at times, but the story it tells is intriguing and the character development is impressive.
26. “Moonlight Mile” (2002)
Based on the Rolling Stones’ song of the same name, “Moonlight Mile” takes place in 1973 and tells the story of how one woman’s murder upends her family and fiancé. This movie might be one of Jake’s most Jewish films: “Moonlight Mile” has a Jewish writer and director (Brad Silberling) and is loosely based on Silberling’s experience when his actress girlfriend Rebecca Schaeffer (also Jewish) was brutally murdered in 1989. The film begins with a Jewish funeral — we hear the Hebrew prayers and observe the tradition using an upside-down shovel to put dirt over the casket. The film offers a remarkable look at grief and how men handle their emotions, plus an analysis of Jewish guilt. There are definitely clichés within this movie, and it can be incredibly slow-paced at times, but it all feels relative to recovering from the death of a loved one.
25. “Wildlife” (2018)
Directed, co-produced and co-written by Paul Dano, “Wildlife” stars Carey Mulligan as Jeannette, a woman who starts to unravel after her husband Jerry (Gyllenhaal) leaves to fight the wildfires in 1960s Montana, much to the chagrin of her son Joe (Ed Oxenbould). For its slow pacing and intense silences, I found the film could get boring. It is only at the end that the film starts to explode, both physically and mentally. Jeanette is a complicated character and Mulligan does a great job bringing her to life: a woman stressed by class and what it feels like to live through “a war at home,” unable to manage and focus on her duties as wife and mother. The cinematography, lighting, and incredible shots of the Montana countryside create a lonely yet beautiful setting that centers the film, helping to tell a story about gender and class and the role of the wife and mother in the home.
24. “Rendition” (2007)
“Rendition” takes on international conflict and how the U.S. government handles national security. When a terrorist on the U.S. watch list bombs a square in Egypt, killing 18 civilians and one American, a call is traced to his supposed contact, Anwar El-Ibrahimi, an Egyptian-born chemical engineer living in America with his family. The government decides to secretly take him in for questioning and torture him for answers, unbeknownst to his family and the world. Jake plays Douglas Freeman, a CIA analyst forced to stay in Egypt to witness Anwar’s torture and questioning, who finds himself between a rock and a hard place – unable to get answers and unable to leave. It’s a story that will have you questioning the War on Terror and the U.S. government’s presence on international soil.
23. “Source Code” (2011)
Jake Gyllenhaal had his first big action star moment in “Source Code,” a thriller about an underground U.S. government program where participants take over another person’s body to stop a crime that occurs. It turns the “Groundhog Day” re-do on its head, envisioning it on a train right before it blows up. This film is very entertaining as we watch Gyllenhaal try to solve a mystery that only we, the audience, know about. It’s not as heavy as a lot of his other films, and very fun to watch. If you’re looking for light Jake fare, this might be your movie.
22. “Highway” (2002)
Jake Gyllenhaal as a stoner? Oh yeah! Starring Jared Leto, Selma Blair, and our boy, “Highway” is one journey that doesn’t have much of a point but is still entertaining to watch. When Jack Hayes (Leto), a pool boy, is discovered having sex with his employer’s wife, a trio of goons is sent after him to break his feet. With his ride-or-die best friend Pilot (Gyllenhaal), the two set off on a road trip to Seattle. Like a few other Gyllenhaal films, I don’t recommend being sober for this movie — it feels like a trip you won’t be able to keep up with in that mindset. The overall pacing, combined with blurry POVs and a very ‘90s soundtrack, is meant to get you into the headspace of each of the characters and works well for what the journey is. However, it isn’t strong enough to hold together like most of Jake’s other movies and could have used more to ramp up the stakes. Then again, that isn’t the point of the movie, but it does make you wonder, what is?
21. “Enemy” (2013)
The more Jake, the merrier, right? Unfortunately, this film tries to prove that wrong. Directed by Denis Villeneuve, Gyllenhaal plays Adam Bell, a college history professor located in Toronto, who, on the recommendation of a colleague, watches a film only to discover that he has a “twin”: the actor Anthony Claire (also Gyllenhaal). “Enemy” nods to the work of Alfred Hitchcock, from the doubling of Gyllenhaal to the blonde women to the inclusion of Ingrid Bergman’s daughter Isabella Rossellini. You need to watch very closely in order to understand the film’s many metaphors and double meanings. Still, the cinematography and color choices, as well as the soundtrack, create an eerie energy, a mystery that only the viewer can solve in their own way.
20. “Life” (2017)
Finally, Jake in an intergalactic space movie! Starring Ryan Reynolds and Rebecca Ferguson, “Life” is about astronauts studying life on other planets. One specimen they encounter turns out to be more dangerous than they thought. Gyllenhaal plays Dr. David Jordan, a medical officer for the ISS who finds himself struggling to survive as the specimen slowly takes over the ship. It’s difficult to do a movie about space that isn’t filled with clichés and doesn’t involve aspects of the space station shutting down or astronauts rushing around trying not to die as fuel tanks break or oxygen is running out. This movie has a few of those tropes, but in the end, it shines on its own, a thriller that borders on horror (there are scenes where astronauts hide and the viewer is. Filled with panic). All in all, it’s suspenseful and kept me on my toes throughout, with an ending that left me haunted.
19. “Stronger” (2017)
Based on the real-life Jeff Bauman who was injured during the Boston bombing of 2013, “Stronger” follows Jeff’s story as he comes to terms with losing both his legs and the impact it has on his loved ones. Jake took the role very seriously and prepared by talking to Jeff every single day, even donning an extreme Boston accent. Unlike most recovery movies, “Stronger” stands out for its decision to focus not on how Jeff learns to walk, but on the human side of his handicap and how he learns to be there for those in his life. In the beginning of the film, we learn from ex-girlfriend Erin (Tatiana Maslany, in a brilliant performance) that Jeff never showed up for anything, and the film focuses more on how he grows into being someone more reliable than he was before his handicap. For a sad but “inspirational” story, “Stronger” delivers.
18. “Spiderman: Far From Home” (2019)
At last, we’ve gotten to Jake’s first big budget blockbuster. Starring Tom Holland and Zendaya, along with many of our favorite characters and actors from the Marvel Cinematic Universe, “Far From Home” is Spiderman’s story of self-reflection as he comes to terms with his role as superhero. The journey is honestly similar to the one I had on my bat mitzvah, when I came to terms with becoming a woman, the pressure on me to lead the temple, the ability to read and interpret the Torah as my ultimate super power. Marvel does its best to provide a complicated story that gets us ready for more adventures from our “friendly neighborhood” Spiderman. Jake is brilliant as the well-developed Mysterio, Spiderman’s new mentor after Iron Man (or so we think…). Overall, the movie is fun and action-packed, even for those who rarely watch superhero movies.
17. “The Good Girl” (2002)
“The Good Girl” tells the story of one woman’s unfulfilling life and the affair that causes it to spiral out of control. Despite the lack of a compact plot, I found the movie interesting in how it subverts so much of the romantic comedy genre. We watch Justine (Jennifer Aniston), a complicated woman working at a small-town dollar store and a mother to the men in her life. Her relationships aren’t sugar-coated and her life isn’t sweet; even her “secret lover,” Holden (Gyllenhaal), is shown to be creepy, his obsession and “die for you” claims deemed strange rather than romantic (If other Jake Gyllenhaal film characters Donnie Darko and Edward Sheffield combined to be one character, it would be Holden.) The film falls short in the sense that it struggles to balance so many elements, but it stays strong with the way it uses Justine’s voice and her perspective to keep us on course.
16. “Brothers” (2009)
Starring Jewish queen Natalie Portman, alongside Tobey Maguire and Jake Gyllenhaal, “Brothers” tells the story of how marine corps captain Sam Cahill’s (Maguire) presumed death impacts his family, specifically his wife Grace (Portman) and his former felon brother Tommy (Gyllenhaal). The most interesting parts of the movie showcase the relationship between Sam’s father Hank (Sam Shepard) and Tommy, who find themselves on opposing sides: Hank resents Tommy for not being like his brother and fighting in the war, instead of getting into trouble, while Tommy blames him in part for Sam’s death. Watching both brothers fight two different wars — the war in Afghanistan, where (spoiler) Sam isn’t dead, but has been captured by the Taliban, and the war at home, where Tommy is trying to get his life back on track after being released from prison — is a compelling narrative that showcases the way the two brothers grow and change. It’s a sad but beautiful story that has a lot to say about the dangers of the military industrial complex for the individual and their family.
15. “The Day After Tomorrow” (2004)
In what might be one of the most relevant movies on this list, this film feels almost at home in the horror genre rather than science fiction. Starring Jewish actress Emmy Rossum as well as Dennis Quaid, “The Day After Tomorrow” is all about what could happen if we don’t act now about the future detrimental effects of climate change and an impending global warming. It begs the questions: Would we be prepared? How would the American people react? Jake plays Samuel Hall, the son of NOAA paleoclimatologist Jack Hall (Quaid), who finds himself stuck in New York City on a school trip, away from his family in DC. I could go on about the politics of this movie — from the way film showcases the most vulnerable populations (low-income people of color) being those the most at risk, to the American “climate refugees” who flee to Mexico, but I will save all that for you to explore. For what the film offers, it predicted a lot of what has come (see: the most recent flooding in the MTA train station in NYC) and may act as a guide for us as we ponder our futures.
Next on the list is another movie about the impact of the climate on the human body’s ability to survive. Inspired by Jon Krakauer’s 1997 book “Into Thin Air,” “Everest” tells the true story of the 1996 Mount Everest disaster and stars Jason Clarke, Josh Brolin and Sam Worthington in performances that showcase the experience of humans pushing themselves to the limit to do something impossible. This film begs the question: How far would you go to experience and see the world at large? These people risked their whole lives for Mount Everest, one of the seven summits, and the film does a good job showcasing why; even the cinematography visually showcases the beauty of Everest and why it’s earned such an iconic status. Jake plays Scott Fischer, one of the rival expedition leaders, who eventually decides to work together with the New Zealand expedition team so that everyone can climb safely (he’s also very chill, in both the figurative and literal sense). I found myself invested in what was at stake for those that risked their life for this journey and gained a newfound respect for those who climb – namely Moses and his journey on Mount Sinai for the ten commandments.
13. “End of Watch“(2012)
This police movie tells the story of cops and their interpersonal relationships, focusing on Jake Gyllenhaal and Michael Péna’s relationship as partners. The trailer makes it look like a high-action film; it’s not at all like that. Some of the most moving scenes are those where they sit in their car talking about their lives. We see them as human while also showcasing how they act on the job. I found the story to be successful at showcasing the humanity behind law enforcement, with their decent attributes, flaws, and motivations on full display and appreciated the interesting use of hand-held cameras. If you’re looking for an intriguing story that showcases the nuances of being a cop, this film might be for you. But also, ACAB.
12. “Southpaw” (2015)
“Southpaw” is yet another Jake Gyllenhaal film that centers on male grief; this time, the story is about a boxer grappling with the death of his wife. This tale of redemption has a lot to say about how toxic masculinity impacts the way men deal with their feelings and use aggressive physical contact as a way to handle their pain. This grieving, violent boxer is a type of character we’ve never seen Jake play (often he’s a military man); it’s one with nuance that is really intriguing to watch, as he fights to get his life back on track and to have custody of his daughter. The journey is absorbing and for a Jake Gyllenhaal movie — the whole reason I’m doing this list, remember — the film feels like a welcome change.
11. “Nocturnal Animals” (2016)
We’ve seen a lot of complicated, confusing Jake films, and this is one of them — but it’s actually quite good. Directed by fashion designer Tom Ford, “Nocturnal Animals” tells the story of Susan (Amy Adams), who works for an art gallery and whose second marriage is crashing down. When she receives a manuscript from her ex-husband Edward (Gyllenhaal), she finds herself haunted by his graphic portrayal of his feelings behind the breakdown of their marriage. Jake does double duty as both Edward and Tony Hastings, a character from the manuscript, and he delivers brilliant performances that showcase the complexities of their emotions. In this noir-thriller that has a dash of camp, there is a lot of commentary on art and how it makes us feel. If you miss a line, you’ve missed an important detail. Ford is very careful with his placing of things and the framing of a shot. The gorgeous cinematography and interesting editing and color theory make the film itself a work of art that one is forced to dig deep to understand.
10. “Zodiac” (2007)
“Zodiac” tells the true story of the late 1960s and early 1970s search for the “zodiac killer,” based on Robert Graysmith’s book of the same name. It’s quite long, but a very compelling movie to get lost in. This film isn’t so much about finding the serial killer (spoiler alert: they don’t) but more so about the people behind the search and their own personal relationships along with how much was at stake. Still, the pacing of the film and the comedic cuts back and forth between San Francisco, Vallejo, and Napa, California showcase the broad length of the case and the complications of trying to bring the killer to justice. Although we aren’t left with answers, “Zodiac” is one entertaining puzzle that the viewer gets to follow along and help solve. At times in can be very frustrating when there aren’t clear cut answers, and the police fail to find clues but the film does get us closer to understanding the thinking behind following one of the most dangerous cases in the U.S.
9. “Donnie Darko” (2001)
It’s now been 20 years since this film was released — a cult classic for Jake fans everywhere. Starring Maggie Gyllenhaal, Jena Malone, Patrick Swayze, Drew Barrymore and a 16-year-old Seth Rogen, “Donnie Darko” is all about religion, time and science intertwining. You know, simple stuff. When Donnie Darko (Gyllenhaal) is told by a costumed bunny rabbit named Frank that the world will end in 28 days, 42 minutes, and 12 seconds, he does his best to try to come to terms with it while the town seems to be falling apart. (To be honest, I still don’t fully understand the film, though I do love it.) In interviews, Jake described the film as “very comforting” at a time when he felt really “lost” and he clearly channels those feelings into the character of Donnie. “Donnie Darko” sits at #9 on this Jake Gyllenhaal ranking because there are times when I felt frustrated by the movie and what it all meant — but take it for what it is and let yourself be confused, for you will certainly enjoy it more.
8. “Jarhead” (2005)
One of Jake’s most well-known films, “Jarhead” is a coming-of-age story in the background of war. Based on the 2003 memoir of the same name by Anthony Swafford about his experience serving in the Gulf War, this film explores masculinity and the military’s impact on male growth in a beautiful, complex way. “Jarhead” isn’t a film about fighting, but what really went on while they waited to fight, the bonds that were formed and the boredom. In some respects, the film feels incredibly fratty, with a bunch of 20-year-old boys who think they are men doing something super dangerous and not understanding the consequences of their actions. Jake plays Swafford as an incredibly confused and frustrated kid still trying to figure out who he’s becoming, having chosen the path of the army because he “got lost on the war to college.” “Jarhead” isn’t like other war films that use death to pull at your heart strings; rather, it forces one to think about the socialization of the military in relation to toxic masculinity.
7. “City Slickers” (1991)
Jake’s first film role (ever!) in the iconic comedy-Western “City Slickers” does not disappoint. “City Slickers” tells the story of three men who go on a wilderness retreat that lets them be cowboys for a week. For as silly as it seems, it’s really a beautiful film that showcases the vulnerabilities of male friendship. These men are shown kissing each other on the face, talking about death and relationships, and trying to better one another. It’s a really great film for deconstructing masculinity — plus there’s an adorable calf named Norman. Baby Jake is great as Billy Crystal’s son and I recommend watching for him but staying for the entertaining journey that teaches three men about life.
6. “October Sky” (1999)
Of all of Jake Gyllenhaal’s movies, “October Sky” is one with the most heart. The film tells the true story of NASA engineer Homer H. Hickman Jr. (Gyllenhaal) and his journey getting into rocketry, much to the chagrin of his coal mining father (Chris Cooper). It’s a tale of resilience, fighting against all odds and toxic masculinity via father-son bonds. Although there are lots of clichés (namely the whole parent vs. child dream situation), the story is very sweet with a wonderful structure. Jake’s performance is filled with innocence and wonder as a kid with the dream of building a rocket. He thrives in scenes opposite the firm and jaded acting of Chris Cooper as his father who struggles to maintain authority when his son no longer wants to follow his path. I may or may not have cried during this movie; I found the characters to be incredibly compelling and well-developed. It’s one coming-of-age story that feels unexpected and has a lot to say about class and educational inequities.
5. “The Man Who Walked Between the Towers” (2005)
Did I watch this 10-minute animated short film adapted from the Scholastic children’s book of the same name that Jake merely narrated? Yes, yes I did. There is nothing to hate about “The Man Who Walked Between the Towers,” which will fill you with nostalgia. It’s a very simple story about Phillipe Petit and his walk across the twin towers via high wire and Jake’s voice is beautiful. If anything, I wish this film was longer so I could listen to 2005 Jake speak all day (#GetJakeAnAudiobookDeal). Even though you don’t actually see Jake, it still deserves the #5 spot.
4. “Nightcrawler” (2014)
When I first watched “Nightcrawler,” I wasn’t that invested, but upon a re-watch for this article, I found real meaning behind the story. “Nightcrawler” is a captivating story about capitalism and the extortion of the underclass by the bourgeoise. It’s a thriller that allows one to fully love, hate and understand its villain. It follows Louis “Lou” Bloom (Gyllenhaal), a petty thief, who becomes interested in video news and filming tragedies for live television. Instead of focusing on the grueling crimes that Lou commits and how he gets caught (or doesn’t, I won’t spoil it), the film focuses more on media and journalistic framings, even bringing in concepts and ideas surrounding white privilege. With his wide-eyes, fast speech, and swift movements, Jake’s performance is terrifying, the viewer never knowing what he will do next. As I watched, I couldn’t help but think about the American dream, the ways in which the media creates moral panics, and the power of clickbait journalism for views.
3. “Okja” (2017)
In this film, Jake Gyllenhaal stars in as Dr. Johnny Wilcox, a doctor of animals, in his wackiest role yet. Directed by Bong Joon Ho of “Parasite” fame, “Okja” is the story of the titular wonder pig who is being raised to be sold and eaten by members of the public, unbeknownst to the young girl, Mija (Ahn Seo-hyun), raising him. Soon, the film becomes a wild goose chase as Mija tries to save Okja from being slaughtered. Unlike a lot of other Jake Gyllenhaal films, “Okja” feels fresh, a magical story that has a lot to say about capitalism and the meat industry that doesn’t lecture you, but doesn’t allow you to sit by and be ignorant. As Dr. Johnny, Jake is outrageous and easy to hate, with a mustache, high socks and sandals, and a high-pitched speaking voice that is annoying to the ears. Yet, I highly recommend this film. The script is masterful, with each detail so carefully thought out. The cinematography is gorgeous, and the CGI of the pigs is realistic and vivid. This is not an easy film; rather, it’s an entertaining journey that teaches the viewer along the way.
2. “Brokeback Mountain” (2005)
“Brokeback Mountain” is not overrated. Directed by Ang Lee, the film follows two closeted gay farm workers in the 1960s and their 20-year secret relationship that follows. With wonderful pacing, a clear structure, incredible acting and well-developed characters, this film does its characters justice, telling their story as masterfully as possible. It is absolutely a tear-jerker for the unfortunate circumstances the characters find themselves in, and how they try so hard to be happy and fulfilled while society’s norms keep them apart. Although Jake Gyllenhaal is straight, his performance as Jack Twist opposite Heath Ledger’s Innis Del Mar is filled with heart and optimism. It does not feed into stereotypes nor make fun of the struggle of gay people to live as their authentic selves; rather, the film focuses on who these men are and how they love. If you haven’t watched it, I don’t know what you’re waiting for. A timeless tale.
1. “Prisoners” (2013)
Finally, we come to the top spot. The best Jake Gyllenhaal movie to date. Directed by Denis Villeneuve, “Prisoners” is about how the kidnapping of two young girls upturns an entire town and their families. I was mesmerized by Jake as Detective Loki, his angry yet calm presence, as he investigated where they went using every means necessary. There is so much depth to each character and their motivations are clear, their pasts beckoning us to question them. Each detail is so carefully thought out and purposeful, attentively curated by Villeneuve for the audience to find. As the viewer gets closer and closer, the details all coming together, more surprises are in store, even until the very end. “Prisoners” showcases how regular people can become villains. I don’t want to spoil the film except to say: Watch it. Jake’s performance is brilliant and magnetic, and “Prisoners” is deserving of the title of the Best Jake Gyllenhaal Film.