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The 15 best Jake Gyllenhaal movies, ranked

Jason Guerrasio   

The 15 best Jake Gyllenhaal movies, ranked
Jake Gyllenhaal.Karwai Tang/Getty Images
  • Jake Gyllenhaal is one of the greatest actors of his generation.
  • The Oscar nominee is known for movies like "Zodiac," "Jarhead," "Nightcrawler," and "Prisoners."

15. "Love & Other Drugs" (2010)

15. "Love & Other Drugs" (2010)
Anne Hathaway and Jake Gyllenhaal in "Love & Other Drugs."      Fox 2000 Pictures

You have to watch this Gyllenhaal guilty pleasure.

In this rom-com (that at times is also pretty dramatic), Gyllenhaal stars opposite Anne Hathaway. The pair deliver great performances: he plays Jamie, a smooth-talking, sex-crazed pharmaceutical rep; she plays Maggie, a woman with early stages of Parkinson's disease.

Casual sex soon leads to the two actually falling for each other. But is Jamie in it for the long road ahead, as Maggie's Parkinson's gets worse?

This is the rare rom-com that has some deep relationship moments, and with the talents of Gyllenhaal and Hathaway, it works.

14. "October Sky" (1999)

14. "October Sky" (1999)
Jake Gyllenhaal in "October Sky."      "October Sky"/Universal Pictures

Gyllenhaal was 17 when he landed the lead role in this coming-of-age drama in which he plays Homer H. Hickam Jr., the son of a coal miner who has aspirations of working on rockets going into space (Hickam would eventually become a NASA engineer).

Even as a teen, you can see Gyllenhaal's star power as he holds his own in the movie that also has Chris Cooper and Laura Dern among the cast.

13. "The Good Girl" (2002)

13. "The Good Girl" (2002)
Jennifer Aniston and Jake Gyllenhaal in "The Good Girl."      Fox Searchlight Pictures

In this indie from director Miguel Arteta and written by "The White Lotus" creator Mike White, Jennifer Aniston plays a bored Texas wife who works at a big-box store.

But things change when Gyllenhaal's character, Holden, shows up one day at work.

The two begin an affair, leading to lots of complications.

Gyllenhaal and Aniston are perfect casting. For Gyllenhaal especially, the movie showcases his heartthrob status as well as his burgeoning dramatic chops.

12. "Southpaw" (2015)

12. "Southpaw" (2015)
Jake Gyllenhaal in "Southpaw."      Scott Garfield/The Weinstein Company/"Southpaw"

This gritty boxing movie was first created for Eminem to play the lead role of boxer Billy Hope, but after the rapper backed out weeks before he was to begin training, the role went to Gyllenhaal.

It's tough to imagine how Eminem would have been playing a boxer, but what turned out happening was pretty great.

Gyllenhaal, who packed on 30 pounds of muscle for the role, is an Adonis on-screen and delivers a passionate performance.

11. "Jarhead" (2005)

11. "Jarhead" (2005)
Jake Gyllenhaal in "Jarhead."      Universal Pictures

Teaming with director Sam Mendes to adapt the gripping memoir by Marine Anthony Swofford on his tour of duty during the Persian Gulf War, Gyllenhaal gives the first performance in his career that showed he could not just carry a movie, but become immersed in his performance.

Playing Swofford, who is filled with insecurities and bravado as he waits for something to happen during Operation Desert Storm, Gyllenhaal shows Hollywood that he wants to be considered one of the best actors of his generation.

10. "Brothers" (2009)

10. "Brothers" (2009)
(L-R) Tobey Maguire and Jake Gyllenhaal in "Brothers."      Lionsgate

A remake of the 2004 Danish film by Susanne Bier, this gripping drama stars Gyllenhaal and Tobey Maguire as two brothers who have feelings for the same woman, Grace (played by Natalie Portman).

Gyllenhaal's Tommy character is a felon just released on parole. Maguire's Sam is a Marine off for another tour of duty. Sam is captured by the Taliban, but his wife Grace is told he was killed in action. This brings Tommy and Grace closer as they grieve.

Sam comes home after escaping the Taliban to the shock of Grace and Tommy's new connection. Sam, suffering from PTSD, feels the two have been sleeping around behind his back, leading to a dramatic ending.

All three are amazing, but it's Gyllenhaal's quiet and subdued performance that is a standout.

9. "The Guilty" (2021)

9. "The Guilty" (2021)
Jake Gyllenhaal in "The Guilty."      Netflix

Gyllenhaal once again remakes a Danish movie. This time reteaming with his "Southpaw" director Antoine Fuqua, the movie focuses on an LAPD cop (Gyllenhaal) who is working at a 911 call center while awaiting a court hearing for an incident.

Answering a call from a woman who says she's been abducted, we watch as the incident meshes with the reason why he's going to have a court hearing, all leading to some dramatic revelations.

Filmed entirely in the call center with the camera fixed on Gyllenhaal, this chamber piece showcases the evolution of the actor, who gives an impassioned performance even when he's just sitting and talking on a headset.

8. "Spider-Man: Far From Home" (2019)

8. "Spider-Man: Far From Home" (2019)
(L-R) Jake Gyllenhaal and Tom Holland in "Spider-Man: Far From Home."      Jay Maidment/Sony Pictures Entertainment

After numerous fails on the blockbuster-franchise front, Gyllenhaal finally hit it out of the park by playing the movie's villain Mysterio.

He plays the sleight-of-hand vibe of the character to perfection.

7. "End of Watch" (2012)

7. "End of Watch" (2012)
(L-R) Michael Peña and Jake Gyllenhaal in "End of Watch."      Open Road Films/"End of Watch"

This edgy cop drama written and directed by David Ayer stars Gyllenhaal opposite Michael Peña as LAPD officers who patrol the gang-infested streets of South Central.

Gyllenhaal's high-octane intensity is on full display here and it's a joy to watch.

6. "Donnie Darko" (2001)

6. "Donnie Darko" (2001)
Jake Gyllenhaal and Jena Malone in "Donnie Darko."      Pandora Cinema

This is the movie that made Gyllenhaal a star.

Two years after "October Sky," he starred in this thriller from Richard Kelly that would go on to become a cult classic.

We follow his character Donnie, a troubled teen who has a vision of a demented-looking rabbit who tells him the world is going to end, as he tries to navigate his life.

With a 1,000-yard stare and dramatic acting that was only just beginning to shine at this stage of his career, the movie is an important benchmark for him.

5. "Prisoners" (2013)

5. "Prisoners" (2013)
(L-R) Jake Gyllenhaal and Hugh Jackman in "Prisoners."      Warner Bros

In Denis Villeneuve's fantastic thriller, Gyllenhaal plays a detective searching for two children who have been abducted with such complexity and rage it's impossible to take your eyes off him for a second.

4. "Stronger" (2017)

4. "Stronger" (2017)
Jake Gyllenhaal in "Stronger."      Roadside Attractions

For whatever reason, this movie never got the attention it deserved and to date is Gyllenhaal's most underrated performance.

Here, he plays Jeff Bauman, who lost both of his legs during the 2013 Boston Marathon bombings. We follow Jeff as he adjusts to his new life.

Gyllenhaal is amazing here as he plays a man who is suddenly thrust into the public eye while still trying to figure out how to function.

3. "Zodiac" (2007)

3. "Zodiac" (2007)
Jake Gyllenhaal in "Zodiac."      Paramount

When we think of a great Gyllenhaal movie, it's usually referencing a role in which he's filled with rage and intensity, but actually, one of his best is where he's none of that.

Gyllenhaal plays the soft-spoken Robert Graysmith, a newspaper cartoonist obsessed with the Zodiac Killer who terrorized the Bay area in the 1960s and 1970s. Director David Fincher uses Gyllenhaal's soft-spokenness and dry comedy to weave the epic story through his character.

2. "Nightcrawler" (2014)

2. "Nightcrawler" (2014)
Jake Gyllenhaal in "Nightcrawler."      Open Road Films

Back to Gyllenhaal madness. There's no other move in his filmography that defines that better than this neo-noir thriller in which he plays an L.A. "stringer" who films violent acts and horrific accidents and then sells the footage to local TV news stations.

Dropping a lot of weight for the role, which just increases the creepy level of the character, Gyllenhaal delivers a performance here that you will never forget.

1. "Brokeback Mountain" (2005)

1. "Brokeback Mountain" (2005)
(L-R) Heath Ledger and Jake Gyllenhaal in "Brokeback Mountain."      Focus Features

Marking his only Oscar nomination to date, here Gyllenhaal plays a 1960s cowboy named Jack who begins a romantic relationship with another cowboy, Ennis, played by Heath Ledger.

The two actors are enthralling to watch as their characters build their forbidden love in secret for decades.

By the end of the movie, Gyllenhaal's performance is etched into our brains though he's no longer on-screen. As we watch Ennis grieve Jack's death, we grieve as well.

What a talent to be able to make audiences feel emotional when you aren't even on the screen.

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