For more than 20 handsome years, Jake Gyllenhaal has been handsoming all over our movie screens, handsomely. He is, of course, more than a pretty, pretty — I cannot overstate how pretty — face. Gyllenhaal is one of the most talented actors working today, on film and stage alike, and adventurously so, choosing interesting and unexpected projects from strange, dark indies to singing Sondheim. He is outstanding, he is incredible, he is a treasure.
He's also a giant dork.
Obviously these things can all exist at the same time. Appearance does not belie humor or geekiness or talent, though the entertainment industry is often at odds about what to do with all those things — it's why it took Ryan Reynolds putting on a mask and a bunch of facial prosthetics to be taken seriously as a major comedic force. But since October Sky, Gyllenhaal has walked the lines of teen geek, moody outcast, creepy weirdo, serious journalist, and, of course, a bubble boy, and he's done so effortlessly, so much so that the world hasn't seemed to give him the level of appreciation and attention he's long deserved.
With Spider-Man: Far From Home, we were given the chance to appreciate all the amazing facets of Jake Gyllenhaal, from handsome superhero to handsome [spoiler, redacted, just see the damn movie]. But those of us in the Gyllen-know have been woke to this for decades. Welcome to the party. The guest of honor is this hot nerd. And we love him.
When Gyllenhaal broke out in October Sky, his first starring role after some time as a child actor, he served us cute-guy-in-English-class-who-reads-Proust-in-public realness and, trust me, 1999-me was very into it. To gaze upon this visage was to see a poet, a serious and gentle soul. And also someone who geeks out playing video games with Princess Vespa, which, like, same.
Listening to the commentary track for Donnie Darko first clued me in to the fact that this gentleman might not be especially serious. Certainly dedicated to his craft and deeply talented, he is also just a big goofball, which is a balm during a commentary track in which director Richard Kelly essentially ruins the movie. (Don't watch the director's cut. Ever.) He makes references to the Simpsons, gives certain moments the MST3K treatment, and shows us all that ultimately, this...
...can also exist as Maggie's goofy-ass brother.
Gyllenhaal's truest sensibility was possibly best captured in this moment with Dustin Hoffman and Susan Sarandon, his co-stars in Moonlight Mile. That sensibility: Cornholio but with abs tho.
Eventually Hollywood realized, "Oh, we have this handsome dude we are just WASTING. Let's make him a video game action thirst trap, albeit a racially insensitive one." And so they made Prince of Persia wherein he looked like this in the film:
While still looking like this on the red carpet:
Cut to Zodiac, a movie where almost everyone is both hot and an eventual Marvel superhero. And, again, and I cannot stress this enough, everyone is also a beautiful dingus. But Gyllenhaal will always be the beautifulest and dingusest.
Most films post-Bubble Boy ignored Gyllenhaal's ability to be a giant weirdo. Because, handsome. It took Okja for people to remember that he is, above all else, an utter goof. Only Bong Joon-ho and a precious pig hippo understood who Gyllenhaal really is: sentient dad shorts.
The great thing about the Marvel Cinematic Universe especially is that it's filled with hot dinks just like Gyllenhaal, most especially Tom Holland, which is why casting him in Far From Home was especially genius. But when you get two hot dinks together, there is only one course of action: to go full Butabi Brothers. Were any of us ready for this? We should have been.
Jake Gyllenhaal has given us two decades of handsome goofery. We don't deserve him. But we're so, so grateful.