Falling in love with Jake Gyllenhaal was, for me, exactly like you see love portrayed in the movies. It wasn't love at first sight, so 14-year-old me watching "Donnie Darko" didn't suddenly decide she wanted to marry the angsty teen whose best friend is a demented rabbit, but rather, it was the first time I really looked at him, gaunt and skeletal in "Nightcrawler" (which one of my friends had to literally drag me to watch). Then, I saw the ridiculously dedicated, insanely talented actor in a different light, and fireworks shot off, choirs sang, and I swooned. Okay, so not literally, but you get the picture. I will admit shamelessly that Jake Gyllenhaal is, without a doubt, one of the most important men in my life.
However, I as well as anyone can recognize his shortcomings — well, fine, maybe not, but I can recognize where people have screwed him over by giving him horrible roles or cheesy scripts. This list is as much an assessment of the movies themselves as it is an assessment of his acting. Some movies are better than others, of course, for reasons other than what the cast brings to the table. Some of Jake's movies probably should never have seen the light of day, not because he is unconvincing, but because they're just bad movies.
But come whatever, rest assured that I will stick by him — and suffer my way through the films in which he is cast.
23. "Accidental Love" (2015)
When I first rented this movie on Google Play and settled into my bed, popcorn at the ready, I was well aware of its awful reviews. I mean, you can just look at the style of Jake's hair on the poster and tell it's a bad movie. But this movie was so bad, in fact, that after it came out in early 2015, barely anyone had heard of it because it was pulled from most theaters. I mean, the movie got 6% on Rotten Tomatoes. Roger Ebert’s crew gave it 1/4 stars. It's literally the story of a woman who gets shot in the head with a nail gun and goes crazy. I knew this, and I still watched it, because what am I if not dedicated to this man, what am I if not loyal, but that was two hours of my life that I will never get back. Jake, baby, you’re worth more than that. And so are we.
22. "Bubble Boy" (2001)
Can I tell you guys a secret? Promise you won't be mad? Okay... I didn't actually watch this movie. I tried, I really did. I watched the trailer on YouTube. I even found the stupid thing on PutLocker. But I couldn't bring myself to watch it. Not only is the premise totally bonkers (really, the boy is allergic to everything? You couldn't have thought up a better reason to put him in a bubble?), but the acting just seems so bad. Okay, maybe not "Accidental Love"-level bad, but almost. If it had come five years later, I'd say just as close to career-threatening. Let's just be glad it didn't and leave this movie in 2001.
21. "Highway" (2002)
Okay, now you can be mad, because I didn't watch this one either. I know I said I'd stick with Jake, but this movie is so early in his career, it shouldn't even count! I mean, Jared Leto looks like Zac Efron! These actors aren't even the same people anymore. IMDb says the plot is about two Vegas boys who take to the highway "akin to Kerouac's 'On the Road'" after Jared's character is caught sleeping with a mobster's wife, and that plus the God-awful trailer were enough to trigger my gag reflex. Take this scene, for instance: "How much longer are we a team?" a deep-voiced Jared Leto asks, sprawled out on a motel bed. "Forever," replies Jake, standing over him. I don't know the context for that interaction, and I don't really want to. I'm guessing you don't either, but if you do, apparently this movie is so off-the-radar that no one has flagged the full version on YouTube.
20. "The Day After Tomorrow" (2004)
Remember that smash-hit flick about the Mayan apocalypse called "2012"? Okay, so take that plot, subtract the supposedly important year, and add a whole lot of snow — bam, you've got "The Day After Tomorrow," a movie about, you guessed it, a true snowpocalypse, and not just one that leaves grocery stores void of all their bread for a week. The movie is largely unremarkable except for a couple cool special effects scenes. High points include a super cute (if quite fumbling) romance between Jake and Emmy Rossum, and one scene of Jake sitting at a breakfast table drinking milk. Lows include, well, basically everything else. Do yourself a favor and don't watch this today, tomorrow, or the day after.
19. "Prince of Persia" (2010)
I'm still really confused as to why this movie happened. Why do video games need to be made into movies in the first place? What does Disney want with theatrical-release live action films? Don't they know no one is going to watch it unless it somehow involves "Pirates of the Caribbean"? Why is it so difficult to get people of color to play characters of color instead of just telling a white guy to grow out his brunette beard? We'll never know the answers to most of these questions. Like, sure, the movie is entertaining, because who doesn't love watching a kick-butt royal couple save the world from a villain trying to turn back time? There are some great action scenes, but honestly, I felt more fulfilled at the end of "Taken 3." It might have something to do with Jake's stringy hair. Yeah, definitely something to do with his hair.
18. "The Good Girl" (2002)
Despite this all-star cast and a 3.5/4 star review from Roger Ebert, "The Good Girl" just didn't stand the test of time. I mean, I definitely wouldn't have ever heard of it if I hadn't high-key stalked Jake's IMDb page. Honestly, I have no idea what to make of this movie, the unfolding of a monumental screwup when a bored housewife starts an affair with a young clerk at the Walmart-wannabe where she works. Throughout the flick and more or less consistently, every character sports a country bumpkin accent thicker than gasoline. The comedy is genuinely funny, but only sometimes. (I'm also a little adverse to comedy, so maybe don't take my word for this.) This movie is definitely not as bad as "Accidental Love," but you know that kind of squicked-out feeling you get looking at the poster? Yeah, if you watch the movie, that feeling doesn't go away.
17. "October Sky" (1999)
So Jake must have gone through his awkward phase from 2001-2004, right? Because he's cute as a button in this 1999 flick as Homer Hickam, a dreamer teenager enthralled by the recent Sputnik launch, looking to build his own rocket and get out of his hometown. For the first part of the movie, Jake plays the bored, hardheaded small-town southern boy convincingly. For the rest of it, he plays the determined, hard-headed small-town southern boy unerringly. Homer is equal parts imaginative and hardworking, and Jake is young and wide-eyed enough to make that dichotomy seem hopeful, not naïve. And that hopefulness translates to the whole movie, not just the character: "Homer," the school football coach says in one of the first real lines of the movie, when Homer keeps charging and getting knocked down by the other team, "You've got guts. But you gotta know when to stop." Lucky for himself, he didn't, not in football and not in life.
16. "Jarhead" (2005)
I've never been big on war movies. "American Sniper" pushed it for me. But "Jarhead" isn't just a war movie; it's a war story, a biopic denoting the incessant boredom ensued by war downtime. Jake's Anthony Swofford is worried about the war, his home life, and his mental stability, but unable to actually do anything productive. Therefore, he is left to contemplation, a subtle thoughtfulness Jake portrays vividly. In this way, "Jarhead" really gets into the homeward-facing minds of the soldiers without actually bringing them home. Sam Mendes, the brilliance behind "American Beauty," directed, so maybe that's why everything is so poignant and, despite its hyper-masculine presentation, delicate. What with Jake already spending half his screen time shirtless, I was expecting a fantasy sequence featuring him in a bathtub filled with rose petals. Unfortunately, no such scene was featured, but a girl can still dream, right?
15. "Rendition" (2007)
Okay, maybe I was just dead tired when I watched this movie last summer, or maybe I was just too starstruck because I was got to see Jake and J.K. Simmons on screen at the same time, but I didn't get it. It's supposed to be about a sympathetic-nobody CIA agent (Jake, naturally) who is forced to witness the torture of a captured Egyptian-born engineer. Meanwhile, the engineer's wife, burdened with the disappearance of her husband, is trying to track him down. This movie is more political than "Source Code" but not as emotional as "End of Watch." However, Jake and the rest of the cast (specifically Omar Metwally, the engineer, actually half Egyptian himself) conveyed enough through their performances that whatever I missed plot-wise, I was never bored.
14. "Love & Other Drugs" (2010)
So this is a cheesy, sentimental romantic comedy — basically everything I hate. But what can I say, I'm sentimental about Jake, and Anne Hathaway is just lovely, and this movie is pretty cute, I can't lie. The plot is thick enough (for a romcom), a "will they make it work?" story concerning a man who sells prescription drugs and a woman with a serious medical condition. And the movie doesn't depend too heavily on tugging its audience's heartstrings... I guess. Either way, Jake fills his role as well as he can. And if the movie is in every other way unredeemable, there is always that one scene. I'm not going to complain about a movie that shows Jake's naked backside, ever.
13. "Source Code" (2011)
I watched this movie expecting a cross between Joe Gordon Levitt's "Looper" and the action hit "Eagle Eye." I don't really have a good reason for that expectation other than the poster design, but either way, "Source Code" defied anything I thought I knew. Jake brings an incredibly sympathetic, inexplicably alluring Colter Stevens to the table in two separate versions of reality, and plays each as if he is the only one in existence. Sound confusing yet? Try watching the movie, a pseudo-magical realism tale about a man trying to prevent a commuter explosion that has, by the time he finds out, already happened. However, the real explosion in this flick is the intense stare Jakes has going on almost the whole time. It makes it a little hard to pay attention to the plot when he's hitting you with the smolder nonstop, but I managed well enough.
12. "Everest" (2015)
Jake's role in "Everest," a climber flick about some teams trying to summit the title mountain herself, didn't appear particularly complex. His character is not morally conflicted or deeply sensitive; in fact, he's not even onscreen for a good portion of the movie. But this character is obsessive, erratic, spontaneous—the complete opposite of many roles Jake has played in the past. Regardless, Jake pulled off the mountain climber Scott Fischer with grace and stamina despite the fact that everyone was actually filming on Mount Everest. Yeah, that's definitely a story for the grandkids one day.
11. "Moonlight Mile" (2002)
Generally speaking, I get kind of on-edge about any movie produced before 2005. "Moonlight Mile," a flick about the aftershocks felt when a man lives with his fiancé's parents after her untimely death, is an exception. The storyline is simple, background music minimal, and characters refreshingly human. Jake plays the dutiful almost-son-in-law with surprising naturalness, as if he really is simultaneously mourning his fiancé and trying to facilitate her parents' mourning. (Even if the poster makes it look like Jake's character is lusting after the mom.) This movie could have easily manipulated its viewers' emotions, but instead of focusing on the sentimentality of grief, it was more of a study in human interaction following great tragedy. If I said Jake's role in 2002's "Highway" didn't count because it was so long ago, then 2002's "Moonlight Mile" is an exception in that way, also.
10. "Donnie Darko" (2001)
This is the first Jake Gyllenhaal movie I ever saw, all because of my tenth grade Latin teacher. I mean, it was on Netflix, so what did I have to lose by watching it? It turned out I had my peace of mind to lose, because this movie jarred me for a couple days afterward. If you think about it too hard, this film will jettison you right into the eye of an existential crisis. But all psychological trauma aside, "Donnie Darko" is a brilliantly crafted movie. Jake plays Donnie, a teenage boy ravaged by apocalyptic visions. And if that's not enough, he had to deal with his real-life sister Maggie on set, who play his on-screen sister. This flick soon became and still remains a huge cult favorite, marking a progression in maturity for Jake's acting career. (Pro tip: If you want to watch this, rent the Director's Cut on Amazon Video instead of watching the Netflix version — it's a whole lot easier to track the story!)
9. "End of Watch" (2012)
You've got fauxumentary horror films, fauxumentary drama films, and then you have "End of Watch." Unlike most of its once-avant-garde genre, this movie about a pair of hero LA cops operates not on shock factor, but on detail. Consistently, Taylor (Jake's character) wears his sunglasses on top of his head; Z (Michael Peña) wears his upside-down behind his ears. Colloquial slang like "dude" and "bro" are repeated ad nauseum throughout conversation. More than this, both Jake and Michael Peña are masters of the brooding, self-aware martyr. They act as if they both truly know how it feels to potentially die for the greater good. And if Jake's chemistry with Anna Kendrick is a little weak, it's probably because their wedding scene plays out like a really embarrassing home movie.
8. "Proof" (2005)
Roger Ebert once said that "Proof" is the kind of movie about math that doesn't require the viewer to have an understanding of math. It's the story of a woman trying to clean out her mathematician father's workbooks after his death. Speaking as someone who both barely passed Algebra and loved this movie, I concur. Jake plays somewhat of brainiac, a little socially awkward but endearing nonetheless. It's a far cry from most of his other roles; usually, he's typecast as the hyper-masculine womanizer for many movies because that's just who he looks like. But Jake pulls off this quietly mindful role beautifully — with intelligence, wit, and, as always, talent.
7. "Southpaw" (2015)
The same friend who dragged me to see "Nightcrawler" and started this ridiculous Jake obsession paid dearly for that by getting dragged to the midnight premiere of "Southpaw" last July. I loved it. He didn't. Different strokes for different folks, right? I will admit, the plot, a comeback story about a professional boxer hit with extreme personal trauma at the peak of his career, replied heavily upon previous boxing films. How could it not? But Jake took his role, one that could have come across as rather cliché, and totally brought it to life. The chemistry between him and Oona Laurence, who played his daughter, is always evident, at times positively incontestable. And whatever the plot lacks in originality, it makes up for in effort.
6. "Zodiac" (2007)
Listen: Fincher hit the jackpot with this trio of actors, all brilliant and talented in their own ways. But the most important bit about "Zodiac" is the tension kept taut throughout the whole flick, characters and audience alike on the edge of their seats to track down this mysterious and dangerous killer. Jake, still somewhat babyfaced, plays the obsessed journalist part perfectly. Granted, he was working opposite the ever-brilliant RDJ, so he had a great teacher easily accessible. Oh, and did I mention the director is David Fincher?! If you couldn't tell from the poster alone (that tagline is just flat-out gorgeous), the movie is well-rounded and 100% worth any nightmares watching it may cause. (Spoiler alert: Sadly, Ted Cruz is not depicted in this movie. I guess people didn't know the truth in 2007.)
5. "Brothers" (2009)
"Brothers" is the kind of movie during which you realize halfway through that you don't know who to pull for. The soldier lost in war or the underdog looking for his place in the world? Jake plays the sensitive ex-con, the family black sheep, and you're wary of him at first, but eventually you're drawn to him for reasons other than because he's got killer scruff. Everything just gets messier as the movie progresses, but throughout it all, Jake's Tommy remains both hesitant and eager, cautious and driven, a complexity of conflicting emotions that throughout the whole flick feels natural, not fabricated. (Side note: Jake sports fake neck tattoos in this movie, "Prisoners," and "Southpaw." I'm sensing a pattern here, and it's not a pattern I mind.)
4. "Brokeback Mountain" (2005)
I don't want to talk about how this movie — yes, the one about the gay cowboys, we get it — got Jake his only Oscar nomination to date. I don't want to talk about how this role won him a much-deserved BAFTA. I don't want to talk about how he is now the godfather of Heath Ledger's children. Above all else, I definitely don't want to talk about Jake's broken Jack Twist with his hands shoved in his pockets, staring out over the lake by Brokeback, southern accent as thick as the tension onscreen as he confesses, "I wish I knew how to quit you." I don't want to talk about any of it, one bit.
3. "Prisoners" (2013)
Jake's role in this movie is probably the most obvious instance of his famous on-set improvisation. His genius Detective Loki, on the hunt for two missing girls, gets a lot of close-ups throughout the duration of the film. If you notice, during the scenes in which he is particularly stressed — when he's interrogating Alex, sitting with one of the girls' fathers in the ABC store parking lot, watching and re-watching investigation tapes — he will blink fast and repeatedly, a nervous tick. When asked about his character's tell, Jake said that it wasn't in the script, but that it just felt like something Loki would do. The director agreed. Plus, the rest of the movie is not only brilliantly written but also expertly cast, all adding up to make a well-rounded, truly exceptional film.
2. "Nightcrawler" (2014)
Did you know that during filming for this movie, without prompting from the director, Jake lost 30 pounds and went weeks without sleeping? All to give his terrifically creepy, beautifully haunting LA crime reporter Lou Bloom a hollow, hungry look. And it certainly worked — not only on screen, but in interviews and public sightings during the "Nightcrawler" period, Jake constantly looked desperate and thin-skinned, almost like a feral animal. Once you watch this movie, that image will become extremely poignant — and will leave you feeling just as hollow and hungry, but for what, you'll always be a little unsure. I certainly count that as a convincing production.
1. "Enemy" (2013)
This movie is number one for many reasons, the most important being: JAKE LITERALLY PLAYS TWO DIFFERENT ROLES. The entire premise of the movie is about two men who are dead-ringer doppelgängers in appearance but polar opposites in character. Jake's Adam is quiet and reserved, a bookish professor. His counterpart, Anthony, is lively and arrogant, a sexually charged movie star. The two characters are separate for much of the movie, but Jake handles the scenes in which they are together — or even more tricky, the scenes in which they are pretending to be each other — with startling grace and clarity. It's a beautiful, beautiful movie, from the writing to the design to the cinematography. This is the kind of movie Jake deserves. This is the kind of movie Jake is worth.
Jake Gyllenhaal has starred in some of my favorite movies ever, and I'm sure they rank so high on my complete list in part due to his genius. But not all of them are memorable for the right reasons. Regardless, I won't judge any one of his films before watching it myself (except for those two, I swear) — but that doesn't mean I'll willingly watch it again.
For his sake (and let's be honest, also mine, because I definitely don't want to sit through another "Accidental Love"), I hope that "Demolition" is as good as the previews make it seem. I'm ready for another complicated, torn Jake-centered dramedy along the same lines as "Love & Other Drugs." Rotten Tomatoes has already given "Demolition" 51%, but I think I'll let myself be the final judge.
A previous version of this article was published on Odyssey Online.