9 best Jake Gyllenhaal movies to watch (and 3 to skip)

Jake Gyllenhaal is Mysterio in Columbia Pictures' SPIDER-MAN: ™ FAR FROM HOME.
Jake Gyllenhaal is Mysterio in Columbia Pictures' SPIDER-MAN: ™ FAR FROM HOME. /

Jake Gyllenhaal's career is full of so many great titles that we have all heard or have seen at least once in our lives. Yet, there are still some titles that we believe don't get enough recognition and should be watched at least once in a while to appreciate their awesomeness.

While there are countless movies to choose from, here are the 9 best Jake Gyllenhaal as well as a few that we think you won't miss out on if you ever decide to skip.

Best films featuring Jake Gyllenhaal

In our humble opinion, Jake Gyllenhaal wouldn't be who he is today without Donnie Darko!

In the 2001 film, Gyllenhaal played the titular role of Donnie Darko, a young teen who is plagued with the knowledge that the world is going to end very soon. Of course, he initially thinks he's going crazy. But once he starts seeing strange thingas in real life, he starts to wonder if he's in a dream or if this is a nightmare reality he must find a way to let everyone know about.

Take a trip down memory lane by watching the trailer for Donnie Darko below!

If you would love to re-watch every second of this thriller, head over to Peacock to stream! However, don't let that be the only film of Jake Gyllenhaal you check out!

Here are eight more films you should stream very soon!

  • Lovely & Amazing (2001) - Tubi | Pluto TV | Peacock
  • The Good Girl (2002) - Showtime | YouTube Movies
  • Brokeback Mountain (2005) - YouTube Movies | Apple TV | Google Play
  • Zodiac (2007) - Pluto TV | Paramount+ | Showtime
  • Nightcrawler (2014) - Starz | Hulu | Amazon Prime Video
  • Southpaw (2015) - Showtime | Paramount+ | Sling TV
  • Okja (2017) - Netflix
  • The Guilty (2021) - Netflix

Jake Gyllenhaal films to skip

If you ever told us that Jake Gyllenhaal was going to star in a film with Spider-Man, we never would have believed you. Yet, here we are!

It's not that Spider-Man: Far From Home wasn't a good movie. (We think it was one of the best Spider-Man films thus far!) It's just, in the grand scheme of things, Gyllenhaal could've easily been played by anyone else and the film still would've remained the same.

In the 2019 film, Gyllenhaal plays the role of Mysterio, a menacing man with a vendetta against Iron Man. Because he can't get to Iron Man directly, he decides to go for his mentee, Peter Parker. He then proceeds to get close to the young teen only to betray him in the end to settle the score between him and Iron Man.

Granted, there is no villain like Mysterio; he's super cool. But there's just nothing in the film that tells us that Mysterio, positively, undoubtedly, had to be played by Jake Gyllenhaal.

Simply put, it just wasn't his best work.

In addition to Spider-Man: Far From Home, we also think the 2010 film Prince of Persia: The Sands of Time and the 2015 film Everest are easy skips since they just fall short in comparison to the other amazing titles in Gyllenhaal's resume.

Even so, if a Sony blockbuster is in his worst three films that says a lot about how accomplished of an actor Jake Gyllenhaal truly is.

Here's where you can watch Spider-Man: Far From Home and the rest of the films we think you should skip.

  • Prince of Persia: The Sands of Time (2010) - Disney+ | YouTube Movies
  • Everest (2015) - Max | YouTube Movies | Amazong Prime Video
  • Spider-Man: Far From Home (2019) - Disney+ | fubo TV

Perhaps you'll find other titles that you think we should add to this list. Either way, be sure to head to any of these sites to stream every second of these Jake Gyllenhaal titles!

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