The Good, The Bad & The Badass: Jake Gyllenhaal

Last Updated on August 2, 2021

Last week, we took a look at the career legendary actress Diane Lane, long a favorite of ours at This week's actor is another favorite…

Jake Gyllenhaal

jake gyllenhaal demolition

It's tough to believe, but Jake Gyllenhaal's been making movies for twenty five years. Born into a showbiz family (along with his very talented sister Maggie Gyllenhaal), he got his start as a child actor. Then billed as Jacob Gyllenhaal, he popped up as Billy Crystal's son in CITY SLICKERS, along with a handful of parts in movies like JOSH & S.A.M. It was in 1998 that Gyllenhaal, in his teens, got to really distinguish himself in the Joe Johnson gem OCTOBER SKY, before moving on to movies like BUBBLE BOY, the cult hit DONNIE DARKO and more before being reinvented into a heartthrob by the time he played Jennifer Aniston's younger lover in THE GOOD GIRL.

jake gyllenhaal donnie darko

From there, Gyllenhaal became a bit of a perennial almost star, having just lost out on playing SPIDER-MAN (for awhile he was rumored to be Sony's backup for the sequels if Tobey Maguire had bailed) before taking a stab at action-hero status with the disastrous PRINCE OF PERSIA. Gyllenhaal fared much better in drama, winning an Oscar nomination for BROKEBACK MOUNTAIN and critical applause for movies like JARHEAD and ZODIAC.

jake gyllenhaal southpaw

It was around the time Gyllenhaal made David Ayer's END OF WATCH that his stock really began to rise, with the one-two punch of Denis Villeneuve's PRISONERS and ENEMY having particular impact. Those films seemed to signal that Gyllenhaal was no longer trying to be a young Tom Cruise or model himself on anyone else. Here he really came into his own, and his follow-up performances in NIGHTCRAWLER, SOUTHPAW and now this week's DEMOLITION further prove the fact that Gyllenhaal is now a full-fledged star on his own terms, and a force to be reckoned with.

His Best Work

jake gyllenhaal nightcrawler

I was fortunate enough to attend the world premiere of Dan Gilroy's NIGHTCRAWLER at TIFF 2014 and it remains one of the highlights of my time at as I truly felt like I was watching the birth of a kind-of classic. While this status won't likely happen for awhile yet (I'd wager a movie has to be at least a decade old before we can call it a classic) NIGHTCRAWLER wound up being a box-office success largely due to Gyllenhaal's megawatt, unconventional performance as a freelance photojournalist whose pursuit of the latest in grime and crime turns him into a full-fledged sociopath. Tough and troubling subject matter to be sure, but Gilroy makes it all pop and Gyllenhaal, who underwent a physical metamorphosis from heartthrob to reedy psycho, has never been better.

His Most Overrated Film

jake gyllenhaal anne hathaway love and other drugs

I had high hopes for Ed Zwick's LOVE AND OTHER DRUGS and while Gyllenhaal does his able best playing a horny sales rep for Viagra in the mid-nineties, the movie demanded a young Tom Cruise. And that's simply not Gyllenhaal, even though this was clearly meant to be his JERRY MAGUIRE. For my money, Gyllenhaal has always been a character actor trapped in a leading man's body, and while him and Anne Hathaway sure look good cavorting around naked together overall this is a big misfire.

His Most Underrated Film

jake gyllenhaal zodiac

Back in 2007, I was working as a marketing rep for Paramount Pictures, and one of the movies I rep'd was ZODIAC. For some reason, it was dumped into the first quarter of the year when an awards-berth would have been more appropriate and the costly movie wound up dying at the box office. Still, it's gone down as a classic in director David Fincher's canon, especially if you watch the extended cut (with a few minor but important tweaks). While I'd argue future Marvel pals Robert Downey Jr and Mark Ruffalo walk away with the movie, Jake Gyllenhaal is effective in a part he was arguably way too young for, as cartoonist Robert Graysmith, whose chronicling of the Zodiac killings turns into a decades-long obsession.

His Best Scene

One of the most effective scenes in NIGHTCRAWLER is the climactic, high-voltage car chase where Gyllenhaal's Louis Bloom literally chases down a story in a mad-cap pursuit of a getaway car, to the horror of his assistant (the great Riz Ahmed) in the hopes of getting a juicy clip for the news. Exciting and darkly funny, the beautifully directed and shot (by Robert Elswit) chase is a highlight and Gyllenhaal's mad intensity puts it right over the edge.

His Five Best Films


Up Next

Befitting his status, Gyllenhaal's dance card is full for the next two years or so. In addition to DEMOLITION, he's got Tom Ford's NOCTURNAL ANIMALS (opposite Amy Adams and Michael Shannon) due out for awards season, and in 2017, he's got David Gordon Green's STRONGER, LIFE (a sci-fi tale casting him opposite Ryan Reynolds and Rebecca Ferguson) and Joon Ho Bong's highly anticipated OKJA.


About the Author

Chris Bumbray began his career with JoBlo as the resident film critic (and James Bond expert) way back in 2007, and he has stuck around ever since, being named editor-in-chief in 2021. A voting member of the CCA and a Rotten Tomatoes-approved critic, you can also catch Chris discussing pop culture regularly on CTV News Channel.