Jake Gyllenhaal is one of Hollywood's top talents, and after a brief marathon of his movies it isn't hard to see why. He's played many different types of characters throughout his career, and in all honesty he's good in just about every single one of them. At least, he is in these ten movies, which are among the best that the actor has offered audiences over the years.
Good guy or villain, bad ass or teenage outcast, Jake Gyllenhaal is always great when it comes to entertaining. These roles rank among the best he’s ever done in his career, and are worth a watch for anyone who hasn’t seen one or two of them yet. These are the best movies when it comes to Gyllenhaal, and should be prioritized for any reader looking to get to know his work better.
10. Spider-Man: Far From Home (2019)
We’d be remiss to close out this feature without making mention of Jake Gyllenhaal’s debut in the Marvel Cinematic Universe. His role as Mysterio was perfect, especially for casual viewers who didn’t know his character was a villain all along. He remains my favorite villain of the Tom Holland era of the Spider-Man franchise, and his revealing Spider-Man’s identity was a catalyst to some big things in the following movie.
9. Prisoners (2013)
Jake Gyllenhaal and Hugh Jackman star opposite each other in Prisoners, and it makes for a captivating albeit disturbing thrill ride. A detective investigating the disappearance of two girls leads to a father taking matters into his own hands. With the acclaim director Denis Villeneuve is getting for his work in Dune as of late, this is one of his movies worth revisiting for reasons beyond the subject of this feature.
8. Jarhead (2005)
Jarhead puts Jake Gyllenhaal in the shoes of former real life marine Anthony Swofford. For those who haven't seen it, this isn't the typical war movie, as it details one soldier's journey during Operation Desert Storm. This Jake Gyllenhaal movie captures a side of modern warfare from a unique perspective not often shown, and is only elevated in the respect that Gyllenhaal’s Oscar-worthy performance is heightened by director Sam Mendes and a great supporting cast.
7. Southpaw (2015)
In a ranked list detailing the best boxing films of all time, Southpaw probably wouldn't be super high. That said, this Jake Gyllenhaal movie has earned its spot here for a performance that generated Oscar buzz, and for how absolutely jacked he got for this movie. He's never in bad shape, of course, but this performance had to have sold a few people on him playing Batman someday. After seeing what Gyllenhaal would look like as The Caped Crusader, I’d be on board with it.
6. Roadhouse (2024)
Jake Gyllenhaal’s evolution into a jacked action hero really took off in Roadhouse, so much so that it didn’t take Amazon long at all to greenlight it for a sequel. It’s high praise for a movie that’s a remake of a classic Patrick Swayze movie, and it flourished with the decision to move the movie’s plot to Florida. Those looking for more balls to the wall action needn’t look any further, this is the definitive movie to check out from the actor.
5. Nightcrawler (2014)
Here's a Jake Gyllenhaal movie where the actor turns on the crazy, although his character in Nightcrawler is far more insane and sadistic than funny. Gyllenhaal plays Louis Bloom, a man determined to make a living as a tragedy cameraman in Los Angeles. The film and Gyllenhaal’s performance are bonkers from start to finish, but it doesn't really hit until that scene where he's laughing watching television and looking around and reacting to no one in particular. It also gets bonus points for being the best Gyllenhaal movie to watch around Halloween in my opinion.
4. Zodiac (2007)
This Jake Gyllenhaal movie isn't more optimistic than many of the others on the list, but at least his character is more of the hero in this harrowing story that makes for one of the most sinister serial killer movies in America's history. Of the selections on this list, Zodiac is the one that best highlights Jake Gyllenhaal's ability to portray an obsessed character, which is often an element in his roles. See this one immediately.
3. Brokeback Mountain (2005)
No one should need a list to know Brokeback Mountain is one of Jake Gyllenhaal's best. Those who have gone this long without seeing it are making a mistake, and missing out one of the best performances of Heath Ledger's career to boot. For Gyllenhaal it's really on another level than any other role he's taken since, and absolutely one every movie lover should experience at least once. It’s wild that an A-List director passed on this one so many actors like Brad Pitt didn’t want to make this movie!
2. Donnie Darko (2001)
No disrespect to everything he's done after, but Jake Gyllenhaal's Donnie Darko remains one of his best movies with a mindbending ending. It features a much different performance than the characters Gyllenhaal would become later in life. It may not be the most groundbreaking performance the actor has ever given Hollywood, but it is the one that really set him on a path to be one of Hollywood's premiere names. In addition to that, it’s one of the more prestigious teen horror films out there, and even includes a surprising appearance from a young Seth Rogen.
1. End Of Watch (2012)
The top Jake Gyllenhaal movie on this list, End Of Watch earns its spot for the gritty story of two LAPD officers just trying to survive the crime-ridden streets. There's action, there's tension, and there are tear-jerking and terrifying moments. This movie is Jake Gyllenhaal at his best, and he looks completely in his element from start to finish. I’ll concede this is a mildly polarizing pick compared to what others may have as the top spot on their lists, but worthy of the top slot all the same.
We love Jake Gyllenhall at CinemaBlend, so of course we’ll be sticking around to see what he has coming up next.
