While my motivations for watching Jake Gyllenhaal’s movies are sometimes shallow, he always delivers fantastic performances. As a big fan with a very obvious crush on the dreamy dude, I’ve seen almost all of his movies. After years of tireless research, I’ve concluded these are my personal favorites.

Tell me with a straight face that Jake Gyllenhaal doesn't have stunning eyes and the aura of a man who knows everything.
Tell me with a straight face that Jake Gyllenhaal doesn’t have stunning eyes.
Photo courtesy of Glenn Francis/Pacific Pro Digital Photography

1. Donnie Darko in the 2001 movie, Donnie Darko

For a long time, I declared Donnie Darko my favorite movie. Do I completely understand it? No, but did anyone fully “get” Donnie Darko?

Even though Gyllenhaal made this film at the start of his career, he gave a hell of a performance. He expertly embodied a multi-dimensional character. Gyllenhaal plays Donnie’s kindness, intelligence, melancholy and outspoken nature so convincingly that he made me fall in love with this bizarre movie.

Young Jake Gyllenhaal in one of his first leading roles.
Young Jake Gyllenhaal in one of his first leading movie roles.
Photo Courtesy of Flickr

2. Detective Loki in the gripping movie, Prisoners

I’m embarrassed to say it took me until this year to watch Prisoners, but it did. And Gyllenhaal was phenomenal as Detective Loki. He’s mysterious, well-intention and driven. And he has a questionable neck tattoo.

Gyllenhaal has played numerous cops/detectives. It’s clear that there’s something appealing about authority to him and thankfully, he plays the roles very well. Gyllenhaal put his heart into this movie and Prisoners is one of the most well-executed, gripping thrillers I’ve seen.

Wow, I guess the man can even make neck tattoos work. Now that’s talent.

3. Edward Sheffield/Tony Hastings in the movie, Nocturnal Animals

In this intense story within a story, Gyllenhaal portrays two men. One is author, Edward Sheffield, and the other is Tony Hastings, the major character in Sheffield’s finished novel. As a writer, I loved this concept and Gyllenhaal’s execution exceeded my expectations.

The trailer does a better job laying out the movie’s concept.

Gyllenhaal navigates both roles with ease and mastery throughout the movie. You never get confused because Gyllenhaal makes sure his performances are starkly unique despite the character’s similarities. Both performances were equally impactful thanks to Gyllenhaal’s acting chops.

4. Jack Twist in the romance drama, Brokeback Mountain (2005)

It’s been awhile since I’ve seen Brokeback Mountain, which may be why it’s lower on the Gyllenhaal list. However, Jake Gyllenhaal and the late Heath Ledger were electric together. Their characters’ love story is one this fan will never forget, no matter how much time passes. As Jake’s shirt says, he was a gay cowboy before it was cool.

The legend himself, Jake Gyllenhaal in his Sunday best.
The legend himself, Jake Gyllenhaal in his Sunday best.
Photo Courtesy of Twitter.

I have to commend Jake and his devotion to this movie. There was no straight male, toxic masculinity found from Mr. Gyllenhaal in this role.

5. Lou Bloom in the creepy movie, Nightcrawler (2014)

With the exception of Southpaw, I would say Jake Gyllenhaal’s transformation for his Nightcrawler role was the most physically drastic of his career. Gyllenhaal’s dedication to playing the slimy, grimy Lou Bloom was evident the second we saw his hollowed cheeks and bulging eyes.

Both the movie and character have an unsettling intensity that Gyllenhaal matches with his performance. This is definitely Gyllenhaal’s least likable role on the list and it was a bit of an adjustment to see him play such an inhumane character, but this proves he has the range.

This concludes my professional love letter to Jake Gyllenhaal and his movie career.