In honor of this week’s 19th anniversary of Jake Gyllenhaal’s iconic film ‘Donnie Darko,’ here are his top five films to watch now!

Written by: Tea Kingley – October 29th, 2020 4:39 pm pst

Jake Gyllenhaal's Top 5 Films

Credit: Newmarket Releasing/Everett Collection

Jake Gyllenhaal is, in my opinion, one of the greatest actors working today. From beginning his career as a child, to appearing in blockbusters such as Spider-Man: Far From Home, and tackling Broadway starring in Sunday in the Park with George and Sea Wall/A Life on Broadway (earning a Tony nom for his work in the latter), Jake Gyllenhaal is extremely versatile. He proved himself performing on stage and on screen and in everything from RomComs to psychological thrillers. He gives absolutely stellar and moving performances in everything he does, which is very rare and extremely impressive.

My favorite Jake Gyllenhaal film and second favorite film of all time is Donnie Darko, which had its 19th anniversary this week on October 26th. The film is a sci-fi psychological thriller, which follows Gyllenhaal in the titular role. He faces impending doom, hallucinations of a man in a bunny suit, and a time warp, not to mention attending high school, falling in love and dealing with mental illness. Also starring Jena Malone, Drew Barrymore, and Jake’s real life sister Maggie Gyllenhaal, Donnie Darko is one of the best psychological thrillers ever and effortlessly includes sci-fi elements to create a masterpiece that will leave you both in awe and frantically googling what it all means. Although I’ve kept the film off off my top five list to make room for others, I just cannot recommend it enough, and with this anniversary and the film taking place around Halloween (there’s even a costume party scene!) now is the perfect time to watch. Without further ado, here are the other top five Jake Gyllenhaal films to watch now!

Credit: Alcon Entertainment/WB

  1. Kicking off this list is the 2013 thriller Prisoners, from acclaimed director Denis Villeneuve and co-starring Hugh Jackman with Viola Davis, Terrence Howard, and Paul Dano rounding out the cast. This brutal film follows Gyllenhaal as Detective Loki, tasked with solving the abduction of two young girls in Pennsylvania. Jackman plays Keller Dover, the father to one of the abducted girls who decides to take justice into his own hands. The film does not shy away from graphic and realistic violence, and viewers will be hooked thanks to the great mystery and suspense that keeps you thinking even after the film has ended.

Credit: Warner Bros.

  1. Another mystery thriller film, Zodiac (2007) tells the story of the manhunt for the famed Zodiac Killer of San Francisco. Directed by the famous and critically acclaimed David Fincher, and featuring performances by Mark Ruffalo, Robert Downey Jr. (Avengers before Avengers even came out!), and Chloë Sevigny, the film is expertly crafted and a great watch. If you love true crime, this film is the one for you!

Credit: Rhombus Media

  1. An early film from indie favorite production/distribution company A24, Enemy was released in 2014 and is a surrealist psychological thriller. In it, Gyllenhaal plays two roles as men who look identical but are entirely different people, with Mélanie Laurent and Isabella Rossellini in supporting roles. It has yet another shocking ending that will leave you perplexed. The film is a very interesting one that, although it’s not well known, is definitely one of the actor’s best.

Credit: Chuck Zlotnick–Open Road

  1. Nightcrawler is a neo-noir thriller released in 2014 that follows Gyllenhaal as a freelance journalist who gets sucked into the corrupt and violent underbelly of Los Angeles in order to make more money from his work. The film is an intriguing and powerful character study that shows how capitalism can corrupt and force the poor and struggling to go to extremes in order to first survive and eventually prosper. Gyllenhaal gives one of the best performances of his career in Nightcrawler, and I would highly recommend watching it for the amazing story and the even better acting.

Credit: Focus Features

  1. Of course, Brokeback Mountain has to be number one. The 2005 romantic drama from director Ang Lee stars Heath Ledger alongside Gyllenhaal as cowboys who were once lovers in the 60s. They are plagued by homophobia (both internal and external), society’s expectations of them, and the pain of intense passion forced to fizzle out before its time. The film also stars Michelle Williams and Anne Hathaway. It was nominated for Best Picture and won three other Oscars, and marks a huge turning point in bringing queer cinema to the mainstream. With stunningly honest acting performances and a moving message, Brokeback Mountain is not to be missed.

Credit: Netflix

BONUS: I’ve seen damn near every film Jake Gyllenhaal has been in, which makes this list incredibly hard to make. Other excellent movies with the actor that I would highly recommend include Nocturnal Animals — from notable fashion designer turned director Tom Ford, this 2016 psychological thriller stars Amy Adams alongside Gyllenhaal and many other big names. It tells the story of two parallel relationships and a horrific kidnapping. 

Okja — this action-adventure film from Parasite director Bong Joon-ho deals with the topics of the environment and animal cruelty and sees Gyllenhaal at his goofiest in an ensemble cast; 

Demolition — although not loved by critics, I really enjoyed this 2015 comedy-drama that follows Gyllenhaal as an initially unemotional man who deals with love and loss that cause a transformation in him. 

Source Code — a science fiction thriller about Gyllenhaal as an Army captain who must find a bomber before he blows up a train. It also has an interesting twist that you won’t see coming. 

If you’re looking for a classic RomCom go with Love & Other Drugs, and if you want a straight up comedy special Gyllenhaal also appears in John Mulaney and the Sack Lunch Bunch as the hilarious character Mr. Music. 

Truly, there’s nothing Jake Gyllenhaal can’t do, and almost all of his films are a must watch. So what are you waiting for?!

About The Author:

Tea Kingley is a senior at Emerson College who is majoring in Marketing and Film. She is passionate about all things entertainment and loves being both in front of the camera and a member of the crew. Tea also enjoys marketing, social media, and writing. She’s a TV, movie, and pop culture aficionado. Tea is always eager to discuss the latest releases and news.

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