Jake Gyllenhaal has done a lot of things you’d expect of a big movie star: been nominated for an Oscar, starred in blockbusters, dated high-profile celebs (Kirsten! Reese! Taylor!). But it also feels like he's never quite reached his potential as an A-Lister. With psychological thriller Enemy out this Friday, we’re taking a look at the arc of his career to see if he’s already peaked.

Beginnings

Jake Gyllenhaal is the scion of a big Hollywood family—his dad was director Stephen Gyllenhaal, his mom producer/screenwriter Naomi Foner, and we all know his sister Maggie. He got his start early, playing Billy Crystal’s son in City Slickers, but his parents kept him from taking bigger roles until he had at least decided to drop out of college (Columbia University, in his case). His first big lead role was as the apple-cheeked hero of October Sky, Joe Johnston’s agreeably hokey small-town ‘50s space race drama. It was well-reviewed and made its budget back: a nice little start for the handsome 21-year-old.

Early Days

He followed up with 2001’s Donnie Darko, an unseen nothing on its release that quickly became the emo cult hit of its generation. No matter what you think of the movie, Gyllenhaal’s performance is undeniably captivating and served as a calling card for Hollywood. A series of supporting roles in indies (Lovely and Amazing, The Good Girl, Highway), a horrifying mistake of a teen comedy (the baffling Bubble Boy) and the lead in a Disney-produced prestige weepie (Moonlight Mile) followed. This is when Gyllenhaal speculation began to skyrocket. He hadn’t even opened a movie, but was considered to replace Tobey Maguire in Spider-Man 2 when Maguire almost dropped out over an ailing back. Audiences were still coming around, but Hollywood was all in.

Stardom

First there was 2004’s The Day After Tomorrow, a genuine blockbuster (with eco-preachy themes) that pulled in more than $500 million worldwide (Gyllenhaal shouldered the lead role with Dennis Quaid as his dad). This, by the way, is the only film on his resume to make more than $100 million domestic, unless you’re including City Slickers.

Then came a busy 2005: while John Madden’s adaptation of Pulitzer Prize winner Proof came and went, Sam Mendes’ Iraq war epic Jarhead collected decent reviews and solid box office. Finally, his achingly romantic turn alongside Heath Ledger Brokeback Mountain notched him true critical respect—along with his Oscar nomination (he lost to George Clooney for Syriana), he won a BAFTA and a few critics awards. At this point, Gyllenhaal could basically do whatever he wanted.

Decline

His first post-Brokeback project is David Fincher’s 2007 masterpiece Zodiac, which was unfortunately a bit of a box office bust. Gyllenhaal’s obsessive go-getter Robert Graysmith is not as easy to love as Mark Ruffalo or Robert Downey Jr.’s work, but it’s fine stuff. In the same year, we had CIA/Middle East drama Rendition, which looked strong on paper—Reese Witherspoon coming off an Oscar win, Meryl Streep, hot-button issues—but bored audiences and critics on its release. It took two years for another Gyllenhaal credit, the underrated but equally grim soldier-returning-home drama Brothers.

At this point, Gyllenhaal’s problem isn’t so much bad reviews as it is lack of box office muscle. So he signed onto 2010’s video game-inspired potential franchise Prince of Persia, got super-ripped, and took on villain Ben Kingsley armed with a couple of swords and a dodgy English accent. It made $90 million domestic on a $200 million budget (it did better worldwide) and was greeted with critical howls. In the same year, Love and Other Drugs, which had attracted Oscar buzz all year, got Gyllenhaal an undeserved acting nomination in the comedy/musical category at the Golden Globes, particularly hilarious considering the film was basically a bland, soggy medical drama. It was largely ignored by audiences.

Rebound

Gyllenhaal, perhaps, was never cut out to topline Hollywood tentpoles. That certainly seems to be his outlook, because he’s shifted over to grittier genre stuff—2011’s charming, somewhat half-baked Source Code and 2012’s underseen and underrated L.A. cop drama End of Watch. Last year, he got the best reviews of his career for the overwrought Prisoners, directed by French up-and-comer Denis Villeneuve, with whom he reunited for Enemy. While Prisoners was not quite good enough to bounce Gyllenhaal back to his peak, it at least reminded people he could act. The double-act performance in edgy thriller Enemy is even more of a tour de force, although the film is getting similarly polarized reviews.

Future?

Also out this year is Nightcrawler, an indie directorial debut from screenwriter Dan Gilroy, and in 2015 there’s mountain-climbing thriller Everest from Baltasar Kormakur (2 Guns, Contraband). But these were likely arranged before Prisoners helped get Gyllenhaal back on the map. What’s really important is what comes next—his rumored role in Antoine Fuqua’s boxing drama Southpaw seems in line with the kind of big-budget Hollywood dramas that should be his ceiling. If Gyllenhaal is eyeing a blockbuster, he should tread lightly, because another Prince of Persia could deal a death blow to his status as a potential marquee idol. But more intense character roles and another Oscar nomination would put him on a far more rewarding path.