Over recent years, Jake Gyllenhaal has become one of the most trustworthy working actors whose movies you’ll watch solely because his name is on the poster (if anyone still picks movies that way). Even when he appears in mediocre movies, you can be sure he’ll give a stellar performance, always giving 110 percent to whatever role he plays. From doing extensive research and putting his body on the line, it’s no understatement that Gyllenhaal gives his all to his work.
The early 2010s saw the actor becoming more selective of the movies he appears in and roles he plays (particularly after the disaster that was “Prince of Persia”), thus kicking off what’s been a brilliant decade for the actor. He appeared in some of the best films of his career and gave some memorable performances in a wide array of diverse films and characters. And the decade is not over yet, with this year alone promising more great films with Paul Dano’s “Wildlife” and Jacques Audiard’s “The Sister Brothers” slated for release later this year.
30. Accidental Love (2015)
By far the worst thing Gyllenhaal has ever appeared in. Just about everyone involved in “Accidental Love” has disowned it. Directed by David O. Russell before he would go on to reinvent himself with a string of critically acclaimed and successful dramas, the director distanced himself from this train wreck by being credited under the pseudonym of Stephen Greene.
Starring Jessica Biel, Catherine Keener, Tracy Morgan and Josh Brolin, amongst others, filming began in 2008 with production reportedly being shut down up to 14 times due to non-payment, which caused most of the cast and crew to walk away.
The series of financial problems, off-screen drama, and creative differences were obvious omens that this rom-com about a girl who’s accidentally shot with a nail gun and forced to live with the nail in her head should’ve stayed buried in the vault.
29. Bubble Boy (2001)
Armed with an interesting and fairly original concept, a capable lead actor and some pretty good cinematography, “Bubble Boy” had all the ingredients to become a pretty good film if only it had one other thing: a good script… or at least a funny joke or two.
One of Jake Gyllenhaal’s worst film also has one of his worst performances. Born without an immune system and forced to live life in a protective bubble (although he seems to have gotten used to it), Bubble Boy runs away from home on a journey to Niagara Falls to stop the girl he loves from marrying her douchebag boyfriend.
Bubble Boy speaks with an annoying whiny voice that’ll get on your nerves after the first minute, the jokes are offensive, and the storyline is beyond idiotic. However, it does make you wonder how such a terrible film could be made and make it past the many different stages of production and release, so kudos for that.
28. Prince of Persia: The Sands of Time (2010)
“Prince of Persia” is known as the movie that indefinitely put an end to Jake Gyllenhaal appearing in blockbusters, and that’s before he even got started. Adding nothing to cinema other than being another entry in the now very long list of failed video game adaptations, “The Sands of Time” is as bad as it gets.
Set in ancient Persia, a young misfit discovers that a dagger he owns contains magic sand which can turn back time when a button on the dagger is pressed. A battle for the dagger and the kingdom begins, inspired by the worst parts of the Pirates of the Caribbean series.
The writing is absolutely atrocious with the whole script filled with terrible dialogue, some unconvincing CGI, cliché storylines, and dull action set pieces. There’s zero to no chemistry between Gyllenhaal and his love interest Gemma Arterton, and the bad filmmaking doesn’t help Gyllenhaal’s performance one bit.
27. Rendition (2007)
Director Gavin Hood has struggled to capitalize on his Hollywood films after the success of his Oscar-winning film “Tsotsi.” Featuring some of Hollywood’s finest actors and an interesting plot based on a true story, “Rendition” is just a dull and boring watch.
Shining a light on the CIA’s controversial extraordinary rendition where a case of mistaken identity saw an innocent man brutally tortured, “Rendition” fails on its good intentions. Its multiple stories and obvious manipulations make its powerful story and political clashes bland. The combined talents of Reese Witherspoon, Alan Arkin, Meryl Streep and Jake Gyllenhaal aren’t enough to save it from itself.
26. The Day After Tomorrow (2004)
When it comes to Hollywood disaster movies, the real star is always the special effects. Aside from Gyllenhaal and Dennis Quaid’s best efforts with their underdeveloped characters, their performances get drowned out by film’s global cooling shenanigans and clichéd narrative beats.
“The Day After Tomorrow” doesn’t make a lick of sense with one major scientific inaccuracy (of which there are many), making the film especially hard to take seriously. But even with its flaws, it’s masterfully directed with a number of memorable sequences and breathtaking visual effects.
25. Southpaw (2015)
If you’re going to make a boxing drama, especially in this day and age, then you better be sure that you have something unique and fresh up your sleeve. As great an actor as Jake Gyllenhaal is, a good performance simply won’t cut it. Which is about the only unique and fresh thing “Southpaw” has going for it.
Putting on the muscle and committing himself fully to boxing, Gyllenhaal gives an intense and raw performance, elevating this by-the-numbers sports drama with his mere presence. This is a shame because a performance like this deserved better than what “Southpaw” delivers.
24. Love & Other Drugs (2010)
It’s hard to know what to make of Edward Zwick’s “Love & Other Drugs.” It’s a mish-mash of many different ideas and genres, some of which work and some of which don’t. It’s a predictable romantic comedy, an awkward erotica, and somewhere in between a complex drama.
Jake Gyllenhaal and Anne Hathaway are what ground the film between its many contradicting stages. Gyllenhaal plays a womanizing pharmaceutical salesman who engages in an overly sexual relationship with a 26-year-old woman suffering from Parkinson’s disease, played by Hathaway. Their no-strings-attached sexual relationship soon turns into something more amidst the boom of and Zwick’s overuse of musical montages. In the end, the film plays it too safe to become something special.
23. Demolition (2015)
After losing his wife in a car accident, a successful investment banker finds it hard to get it together. Sending a series of complaint letters to a vending machine company, he strikes up an unlikely bond with one of the company’s customer reps, who helps him destroy his old self to start anew.
There are parts of Jean-Mac Vallée that are overly familiar and its messages are heavy-handed to a fault. But as always with these types of films, it’s the performances that keep it together with Gyllenhaal and Naomi Watts giving “Demolition” some life. It’s not bad; in fact, it’s enjoyable for some reason, but isn’t memorable either.
22. Highway (2002)
What? A stoner comedy/drama with Jake Gyllenhaal and Jared Leto playing two wacky characters who go on a road trip to Seattle during the 90’s grunge era and getting caught up in some crazy scenarios and meeting a whole host of interesting characters? What?
21. Life (2017)
Looking to take a break from the dramatic and complex characters and movies he’s known for, Jake Gyllenhaal looked to dip his toes into something more fun, and thus we have “Life,” an interesting yet disappointing science fiction/horror that reminds you of similar and superior films.
A crew on an international space station encounters the first sign of life in outer space when a probe from Mars returns with a mysterious sample. What starts out as a historic discovery soon turns into a fight for survival. Featuring a game cast that includes Ryan Reynolds and Rebecca Ferguson, at the end of the day, “Life” just makes you want to watch “Alien.”