Jake Gyllenhaal is one of today’s hottest young actors. The films that really launched Gyllenhaal’s film career were October Sky and the dark indie darling, Donnie Darko Since those early roles, Jake Gyllenhaal has displayed a wide acting range starring in serious movies dealing with gay issues, mental illness, and serial murder, but he is equally as comfortable in action thrillers and romantic comedies. In probably his most notable performance, Gyllenhaal was nominated for the Best Supporting Actor Oscar for his role as a gay cowboy in the critically acclaimed Brokeback Mountain
Jake Gyllenhaal is the son of director Stephen Gyllenhaal
(Waterland) and screenwriter Naomi Foner (Running on Empty). Gyllenhaal is also
the brother of Maggie Gyllenhaal (Crazy Heart The Dark Knight) who played his
sister in Donnie Darko. His brother-in-law, Peter Sarsgaard, costarred with him
in both Jarhead and Rendition to really keep things all in the family.
This ranking of Jake Gyllenhaal movies is based on the
rankings of members at Rankography best movies, a group of movie bloggers and
other knowledgeable movie fans. After reviewing this list of top ten Gyllenhaal
movies, I found myself thinking about how interesting most of his movies have
been. This is not only a testament to Gyllenhaal’s acting chops, but to wise
selection of film roles with only a few misses, such as King of Persia. It will
be exciting to continue tracking Jake Gyllenhaal’s career.
10. Jake Gyllenhaal Movies: Rendition (2007)
A Serious Thriller about Terrorism and Homeland Security
Jake Gyllenhaal finally plays a grown up…a very serious
one with serious faces and serious conversations. In 2007’s Rendition, Jake
Gyllenhaal stars as CIA analyst, Douglas Freeman, in a political wartime
thriller aimed at showing the length at which a government will go under the
guise of protecting freedom.
This Gyllenhaal movie is a serious action drama which also
features a star-studded cast including Meryl Streep, Alan Arkin, Reese
Witherspoon and Gyllenhaal’s brother-in-law Peter Sarsgaard. This was the first
role that he combined with his current girlfriend, Reese Witherspoon so it is
also interesting to watch their chemistry develop.
Jake’s ability to combine both serious and sympathetic tones
lends credence to his role as a CIA agent who begins to suspect that the
alleged terrorist he has been interrogating may have offered a false confession
and is, in fact, innocent and wrongly accused. Because of his sensitivity in
this performance, we can believe that his moral compass is itself being tortured
as he decides whether to do what he knows is right…or to remain on the side
of his own country and government.
9. Love and Other Drugs (2010)
An Interesting Jake Gyllenhaal Romantic Comedy Drama movie
Love & Other Drugs opened to mixed reviews but the praise
always seemed to focus on two points — it was lauded as a rare
“adult” romance and was also acknowledged for the nuanced and
charming performances of the two leads, Jake Gyllenhaal and Anne Hathaway.
Much like this year’s, Moneyball (with Brad Pitt), this
Gyllenhaal film is also based on a non-fiction book that would seem to be
rather boring and unlikely fodder for a big-screen translation…in this case,
a romantic comedy. However, unlike the business of baseball, this film focuses
on the sometimes cut-throat nature and politics of pharmaceutical sales.
Jamie Reidy (Jake Gyllenhaal) is a young playboy who stumbles into the fast-paced world of pharmaceutical sales after being fired from his last sales gig for sleeping with the boss’s wife. At his new employer, drug behemoth Pfizer, he is tasked with pushing their anti-depressant Zoloft over the rival Prozac. While meeting with Dr. Stan Knight (Hank Azaria), Jamie meets patient, Maggie Murdock (Anne Hathaway). They quickly find themselves between the sheets in a no-strings-attached relationship — at least it starts out that way.
We soon learn that Maggie is in the early stages of
Parkinson’s and things start to get complicated. This film is both a romantic
comedy and a serious drama dealing with the reality of dealing with this
debilitating disease. With less appealing actors than Jake and Anne, the uneven
mood and wobbly plot of this film may have gone completely off the rails…but
they manage to keep this one lively and entertaining.
Love & Other Drugs was directed by Ed Zwick (Crumb and
Ghost World) and makes for an interesting date night flick that can be enjoyed
equally by both sexes. It’s also a good opportunity to see Jake Gyllenhaal in a
more mainstream and playful role than some of his darker and more complicated
8. Jake Gyllenhaal Movies: Brothers (2008)
A Stretch Role for Jake Gyllenhaal in this Edgy Drama
Brothers is another favorite of mine from Jake Gyllenhaal’s movies and the last one that my husband will admit to shedding a tear. This remake of a Danish tearjerker — both of which were inspired by Homer’s epic poem, The Odyssey — stars Jake Gyllenhaal, Tobey McGuire, and Natalie Portman. In an interesting role reversal, Jake ditches his Jarhead uniform and plays, Tommy Cahill, an ex-con burnout brother to decorated Marine hero, Capt Sam Cahill (McGuire).
After McGuire’s character goes MIA and is presumed dead in
Afghanistan, Tommy (Gyllenhaal) comforts Grace Cahill (Portman) and begins
helping around the house and providing solace to his sister-in-law and two
nieces. Their relationship grows comfortable and ultimately tragic when Sam
returns home, alive, but scarred from what he was forced to do while in
captivity. McGuire, in his Academy Award-nominated performance, most come to
grips with both his past actions and his current relationship with his family.
It was interesting seeing Jake Gyllenhaal play the immature
misfit in this film (with requisite neck tattoo). Despite having played largely
more straight-laced roles, Gyllenhaal shows his range to dive into this more
edgy character. And even though it was McGuire that earned many of the
accolades for portraying the Marine with Post Traumatic Stress Disorder, it was
Gyllenhaal’s calm and care-free bravado that helped balance the psychosis of his
7. The Good Girl (2002)
Gyllenhaal Pairs with Aniston in this Romantic Comedy
Many might remember The Good Girl as Jennifer Aniston’s first foray into the film from her hit TV sitcom, Friends, but this charming film also starred Jake Gyllenhaal as her tortured young love interest. Here Jake plays a slightly more contrived and banal “Donnie Darko”-type. However, this movie is good satire and Jake nails this caricature of a post-adolescent misanthrope.
This was a daring, breakout role for Gyllenhaal, especially
on the heels of the dark indie, Donnie Darko and the teenage drama, October
Sky. He shows his range as an actor who can be as adept at understated comedy
as well as more serious drama.
And while his role and performance are critical to the storyline, he is also careful not to overshadow Aniston’s lead, as this film is definitely her story and the character for which the title is named.
6. Source Code (2010)
Gyllenhaal’s Race Against Time in Another Time
Source Code was notable for action movie for a number of reasons. First, for Gyllenhaal, he was given the chance to prove himself as a credible male lead in a sci-fi action film. Second, Source Code is also the sophomore directorial film feature of Duncan Jones (the son of legendary rocker David Bowie) whose first sci-fi thriller Moon (starring Sam Rockwell) won over critics and fanboys alike and is considered one of the best sci-fi films of the decade.
Source Code is set in Chicago in the near future and Colter Stevens (Jake Gyllenhaal) is a government agency that is sent into the past to discover the perpetrator of a terrorist attack on a commuter train and thereby prevent the terrorists’ future attacks. Throughout his journey, Stevens wrestles with questions of his own identity and mortality.
On the doomed train, he meets and falls in love with
Christina Warren (Michelle Monaghan), one of the passenger’s destined to die in
the attack. Stevens decides to tempt fate and change the course of the future
to save Christina…much to the disapproval of his government superior, Capt
Colleen Goodwin (Vera Farmiga).
This an exciting action-packed film and Gyllenhaal shows
that he can successfully play the role of an action star (albeit a slightly
less traditional one). His credibility and confident performance also helps the
audience “suspend disbelief” at all of the potential plot holes that
sometimes plague this time-travel flick.
5. Jake Gyllenhaal Movies: Jarhead (2005)
Sam Mendes and Jake Gyllenhaal Combine in this Desert Shield Drama
Jarhead is a biographical war film based on former Marine
Anthony Swofford’s (Jake Gyllenhaal) 2003 book about his experiences in Saudi
Arabia prior to Desert Storm and his experiences fighting in Kuwait. After
Swofford’s sobering stint in the notoriously ruthless Marine boot camp, he is shipped
off to the Middle East for active duty in Desert Shield. What unfolds is days
of boredom in the hot desert sun, followed by the quick Desert Storm conflict.
Jarhead fell a bit flat for me and for most critics. I
remember being quite excited to see this movie – mainly because I was excited
to see what Sam Mendes (American Beauty, Revolutionary Road) would do with the
material. Unfortunately, I think the ‘boredom’ aspect of Swofford’s experiences
dominated the film so those expecting a typical war movie ended up
disappointed. However, in reality this is probably a realistic portrait of the
war in the Middle East and definitely worth a viewing for the solid
performances from Gyllenhaal, Jamie Foxx and Pete Sarsgaard.
4. Jake Gyllenhaal Movies: October Sky (1999)
A Heart Warming Drama About Beating the Odds
October Sky is a true story about the struggle between
generations in the mining town of Coalwood. Homer Hickam (Jake Gyllenhaal) is a
kid with a strong curiosity and a dream of going to college. He is inspired by
the launch of the Sputnik rocket in the 1950s and starts playing around trying
to build a toy rocket. His father, John Hickam (Chris Cooper), is a respected
supervisor and safety minded leader of the men that go down in the local coal
John dismisses Homer’s obsession with rockets initially as
child’s play knowing full well that Homer will one day end up in the mines with
him and Homer’s brother. However, Homer is inspired by his science teacher,
Miss Riley (Laura Dern), to enter his rockets into a regional science fair that
carries with it a college scholarship. Homer and his friends become obsessed
with winning the fair but along the way he draws the ire of his father who
ultimately forbids Homer from participating.
This film does an excellent job of highlighting the
generational struggles between the old guard that both fear change and also
attempt to hold down someone trying to escape the coal mines, and the young
ambitious generation looking for a way out of Coalwood. Chris Cooper is one of
my favorite character actors and he is excellent as Homer’s crusty, but
respected father. Jake Gyllenhaal is fantastic as a wild-eyed teenager whose
sky has no limit and achieves the impossible and leaves Coalwood to become a
While many may think this is a family or children’s movie,
it is not. This is an excellent drama about a true story of achievement against
3. Brokeback Mountain (2005)
The Most Unusual Western Drama You Will Ever See
Ang Lee’s Brokeback Mountain was one of the most decorated films of 2005 and quite a follow-up to Lee’s Hulk comic book movie. By now, most people know the premise of this film; two male cowboys, Ennis Del Mar (Heath Ledger) and Jack Twist (Jake Gyllenhaal) hired to herd sheep in Wyoming during summer in their late teens. Over the course of some intense wilderness experiences, the two develop a deep bond that develops into something more after a night of heavy drinking.
During the rest of that summer, the two recognize that they have developed something far deeper than friendship but move on with their lives separately given that homosexuality is not even an option in their cowboy culture. Instead, they must deal with that love in the backdrop of marriages and 1950s conservative culture.
This unorthodox “western film” is clearly more of
a drama than a cowboy movie. And, there are quite a lot of ‘spoilers’ to be
revealed when writing about this movie, so I will avoid spoiling but to say
that the last scene being one of the most heart-wrenching, well-acted performances
of the last decade. The film won was nominated for 8 Academy Awards, including
nominations for both Gyllenhaal and Ledger, and won 3 for Best Director, Best
Adapted Screenplay and Best Original Score.
2. Jake Gyllenhaal Movies: Donnie Darko (2001)
A Sci-Fi Mystery Drama with a Cult Following
Donnie Darko is an American indie darling from the early
2000s. This film has a huge following among techies and GenXers, which is not
surprising given the popularity of such former TV series as Lost and Heroes.
The film covers the potential of an alternative universe and the potential of
Donnie Darko (Jake Gyllenhaal) is a high school teen who narrowly escapes (or does he?) a fluke accident in which his room is destroyed by a fallen aircraft engine. The film covers the psychological challenges of his narrow escape. He begins having visions of a man-sized rabbit named Frank. Donnie Darko is a unique blend of drama, mystery and science fiction genres.
While this Jake Gyllenhaal film made very little at the box office (~$4MM), Donnie Darko’s large cult following has made it a long-term success. In fact, a 2-disc Director’s cut of the film was released in 2005 and a ‘sequel’ in 2009, S. Darko. This film is also a unique opportunity to see Jake Gyllenhaal and sister Maggie Gyllenhaal playing brother and sister in a movie.
1.Jake Gyllenhaal Movies: Zodiac (2007
An Excellent Mystery Thriller about the Zodiac Killer
Zodiac is one of my absolute favorite movies of the last 10 years. Directed by film genius, David Fincher (Se7en, The Social Network and The Girl with the Dragon Tattoo), Zodiac chronicles the hunt for the notorious Zodiac serial killer who stalked the San Francisco Bay area in the late 60s and early 70s. In typical Fincher fashion, the production design of this film is flawless, immersing the viewer back into the late 1960s. Fincher manages to adapte the rather clinical non-fiction book into a taut thriller of a film.
Robert Graysmith (Jake Gyllenhaal), a one-time cartoonist for the San Francisco Chronicle, becomes consumed with the hunt for the Zodiac killer. Graysmith actually went on to author the aforementioned book about this hunt. While Gyllenhaal seems an unlikely candidate to play the relatively awkward and nerdy Graysmith, he absolutely nails it and we empathize with his intense desire to solve this mystery. Gyllenhaal plays alongside a star-studded cast that includes: Robert Downey Jr., Mark Ruffalo, Chloe Sevigny and Brian Cox.
Zodiac opened to fantastic reviews but made very little at the box office. So, for some of you, this might be a ‘hidden gem’ of a film that is an absolute must-see the film. It has since developed a bit of a cult following in the mystery thriller category primarily because of the outstanding performances by Gyllenhaal and Downey Jr.