The most memorable Jake Gyllenhaal roles

Gyllenhaal made his film debut in “City Slickers,” but that was in a small role as a kid. His first significant role of note came in “October Sky,” when he was playing the real person Homer Hickam. It’s a gentle, feel-good drama about a boy who dreams of working with rockets. Eventually he would. Gyllenhaal had to shoulder the load, and he showed he was up to it.

Hey, when you are beginning your career you have to take some questionable roles sometime. Gyllenhaal got the chance to star in a studio comedy in his early twenties! Now, he also hasn’t been in many comedies since, perhaps with good reason. Not that Gyllenhaal is at fault for the poor quality of “Bubble Boy.” However, it’s remained a memorably bad film, mostly because it was an early outing for a future star.

Yes, the same year he starred in “Bubble Boy,” Gyllenhaal also made the cult classic “Donnie Darko.” Now, the cult of this movie has perhaps waned a bit in the intervening years. That being said, when “Donnie Darko” came out, it was something approaching a phenomenon. People who liked it tended to really like it, and there was Gyllenhaal in the center as Donnie.

Gyllenhaal hasn’t ever really done a true “romantic comedy,” and even “The Good Girl” doesn’t quite qualify. It’s closer than he tends to get, though. While this is a vehicle for Jennifer Aniston, and some of her best work from a craft perspective, Gyllenhaal is a vital piece of the story and handles his role deftly.

Roland Emmerich tends to fill his movies with notable names, but not movie stars, and lets the special effects take center stage. As such, it was definitely a step up for Gyllenhaal to be one of the leads in this ecological disaster flick. Not Emmerich’s most beloved work, but a solid action film that boosted Gyllenhaal’s career.

This is, to date, probably still the first movie people think of when they think of Gyllenhaal. It was controversial. It was an Oscar darling. Gyllenhaal and Heath Ledger’s respective turns as clandestine lovers were integral to the hype around “Brokeback Mountain.” Interestingly, only Gyllenhaal got an Oscar nomination, his only one to date.

Heading into 2005, there was the thought that “Jarhead,” not “Brokeback Mountain,” could be the movie that got Gyllenhaal an Oscar nod. It was kind of a proto-“The Hurt Locker” in that sense, in that it was a war movie that was about internal battles more than anything else. It didn’t quite pop like Kathryn Bigelow’s Oscar winner, but it succeeded.

It’s not surprising that David Fincher made a movie about the Zodiac Killer. It’s also not surprising that he instead primarily told a story about men who destroyed themselves trying to figure out who he was. A lot of people consider this Fincher’s best movie, and that’s really saying something.

Gyllenhaal took his shot on being in a blockbuster action series…and it flopped. Granted, Gyllenhaal probably should have never been playing a character called the “Prince of Persia” to begin with. However, this movie wouldn’t have worked with anybody in it. It’s the most notable flop in Gyllenhaal’s career. As we always say, “memorable” doesn’t always mean “good.”

There were hopes that this raunchy, R-rated romantic comedy could also be an awards play. Gyllenhaal’s costar, Anne Hathaway, mentioned “Love & Other Drugs” when she hosted the Oscars. You remember those Oscars, of course. In a way, they are weirdly responsible for helping to make “Love & Other Drugs” more memorable.

Duncan Jones made a splash with “Moon,” giving himself a bigger budget and a chance to continue doing his trippy sci-fi thing. Gyllenhaal plays a guy sent into a recreation of a train explosion over and over to try and figure out who did it. It’s almost like a procedural version of “Groundhog Day.” Critics loved it, and it was a hit, if not quite a true blockbuster.

For the first time in his career, Gyllenhaal served as an executive producer on one of his films. “End of Watch” is a down-to-earth cop drama featuring Gyllenhaal and Michael Pena as the leads. Pena probably popped a bit more, but that’s in part because we were used to Gyllenhaal doing such steady and reliable work.

“Prisoners” is a punishingly-bleak movie. Some people have no interest in that. Denis Villenueve is not afraid to dive into the darkness, and Gyllenhaal went along for the ride. People who could withstand the punishment do tend to laud praise on “Prisoners.”

This is another movie from Villenueve. Yes, Gyllenhaal starred in two films from the same director in the same year. Maybe they got burnt out on each other, because they haven’t worked together since. “Enemy” is showy, as Gyllenhaal gets to play two roles, that of a man and his mysterious exact double.

All told, this is probably Gyllenhaal’s best work. The actor got into the whole “physical transformation” thing with this role, and that includes in his acting work and the way he carried himself, not just losing some weight. He’s hypnotic and unnerving as Lou Bloom, an amoral striver who stumbles into the world of news by buying wholeheartedly into the colloquialism, “If it bleeds, it leads.”

In classic actor tradition, Gyllenhaal followed up a movie where he got lean and squirrely by bulking up to play an athlete. Here, the actor plays a boxer in a fairly dark film written by Kurt Sutter of “Sons of Anarchy” fame. It’s not exactly a crowd pleaser, but it turned some heads.

A movie about the Boston Marathon bombing so soon in the wake of the event could have been awkward. It could have felt trite or heavy handed, not doing justice to the actual tragedy. Fortunately, people were generally pleased with “Stronger.” Perhaps that’s because it narrowed its scope a bit and focused on one man. That would be Jeff Bauman, who Gyllenhaal plays.

Bong Joon-ho is an Oscar winner now. He’s always been a bit of an oddball director, though. “Parasite” isn’t exactly a by-the-books film, and he’s also the man behind movies like “Snowpiercer” and “Okja.” This environmental parable features a giant pig and perhaps the most going-for-it turn of Gyllenhaal’s career. It’s either this or when he played Mr. Music in John Mulaney’s Netflix special.

This is a Netflix horror movie about killer art. It’s called “Velvet Buzzsaw.” Gyllenhaal’s character is named “Morf Vandewalt.” What more do we need to say? You never forget the name “Morf Vandewalt.”

It wouldn’t have been surprising if Gyllenhaal had been cast to play a superhero at some point. As such, he was pretty perfect casting as a villain pretending to be a hero. In the first MCU film post-“Infinity War,” Gyllenhaal plays Mysterio, a very convincing fraud who puts a grieving Peter Parker through his paces. The Tom Holland “Spider-Man” movies are among the best Marvel has done, and the villains are a key reason why.