Jake Gyllenhaal surprised the Saturday Night Live audience this week, appearing alongside host John Mulaney as a pyjama-clad traveller who likes being felt up by security in a deeply offbeat sketch about LaGuardia Airport. He joined the cast as one of a handful of weirdo characters who sang a reworked Broadway number in an ode to New York's supremely unpleasant airport. But none were weirder than Gyllenhaal’s pervy take on Wicked’s “Defying Gravity.” Somewhere between earnestly singing “you don’t have to use the front of your hands” and getting lifted off stage with a final screech, this cameo is the latest proof that Gyllenhaal is at his best when he embraces his bizarro side.
For anyone who has missed Gyllenhaal’s recent work on Netflix, this odd turn might have come as a shock. Audiences probably know him best as a hot prestige level actor in roles such as: hot pharmaceutical rep, or hot gay cowboy, hot high school student stuck inside a library during a climate crisis, or hot Marvel villain. But there's always been another deeply strange side of him that he's been really leaning into in the last few years and specifically in recent months.
Earlier this year, Gyllenhaal made a cameo on Mulaney’s Netflix children special, John Mulaney & the Sack Lunch Bunch, playing a character named Mr. Music who is an unstable children's teacher. Gyllenhaal's character blasts the kids for their ignorance, then sings a musical number that seems like it could end with an emotional breakdown at any moment. It's strange. It's hilarious. And Gyllenhaal looked like he was having the time of his life. And why not? There's something really charming about seeing this pinnacle of Hollywood attractiveness fully leaning into the absurdity—kind of like finding out that the quarterback of your high school football team was deeply into Magic: The Gathering.
And sure, the weirdness is jumping out a bit more regularly than it had in the past, but make no mistake: Jake Gyllenhaal has always been a little off-kilter. Of all of his films, it's likely that none are more beloved than his cult-classic Donnie Darko. In 2001, a 20-year-old Gyllenhaal starred in the psychological thriller as a high school student who is tasked with saving the world from certain destruction when he's visited by a demonic-looking rabbit. Since then, his career has been a constant push and pull between terrible roles that fuel the box office (Love and Other Drugs and the garbage fire that is Prince of Persia come to mind) and stranger roles in Zodiac and Nightcrawler and even Jarhead seem to be what truly defines his career. Gyllenhaal could have had a successful career as simply the hunk in the latest summer blockbuster. But, instead he takes risks in small roles and passion project indie movies, where he makes bold, bizarre choices. And not enough actors are willing to take such big swings so often.
Last year, Gyllenhaal starred in Netflix's Velvet Buzzsaw, playing Morf Vandewalt, a pansexual art critic who suffers from hallucinations. Two years before that, he played Dr. Johnny Wilcox, a manic zoologist reminiscent of a pessimistic, speed-driven Steve Irwin in Bong Joon-Ho's Okja. Each performance is Gyllenhaal, perfected, even if it goes without recognition from the awards circuit. Even his Marvel character was a little strange—playing Mysterio, a supposed good guy, who was really just a bitter Silicon Valley asshole with a lot of money and technology.
This is a time in Hollywood that is dominated by reboots and sequels. It truly feels like nothing is original anymore. Yet, here is Gyllenhaal giving us unique characters and performances. In an industry where taking risks is a gamble with a studio's bottom line, Gyllenhaal isn't afraid to try something different. Even if it's just a cameo in a comedy special, or a random musical number on a sketch show—nothing is above or below Gyllenhaal.
While the box office fails to come up with any idea that isn't a superhero flick or a remake (and no offense to either—Gyllenhaal did, after all, star as Mysterio in Spider-Man: Far From Home), Gyllenhaal has set his sights on being the unique one. As cinema evolves and new stories are harder to find, this chapter of Gyllenhaal is mostly in opposition to everything that Hollywood is leaning on right now. In a sea of predictable roles, Gyllenhaal is choosing to be strange and bizarre, and your Netflix queue is all the better for it.
Justin Kirkland is a Brooklyn-based writer who covers culture, food, and the South. Along with Esquire, his work has appeared in NYLON, Vulture, and USA Today.
