Both Jake and Maggie Gyllenhaal have shown themselves as very talented actors with both of them starring in consistently good movies and getting praised for their acting. Along with works that are critically acclaimed, their films typically perform very well at the office and are loved by the audience. Even if they aren't, their performances typically are.
Moreover, the two siblings have even starred in some cult classics while their filmographies contain movies of a variety of genres, showcasing their versatility. To fully appreciate their impact on modern cinema, it's worth looking at their highest-rated movies that viewers have deemed to be the best in their careers.
Stranger Than Fiction (2006) - 7.5
Stranger than Fiction is a fantasy comedy-drama that might be somewhat forgotten these days, but it was actually well-received back in 2006. Starring Will Ferrell in the lead, the movie also includes such cast members as Maggie Gyllenhaal, Emma Thompson, and Dustin Hoffman.
The story follows an IRS agent named Harold Crick who starts hearing a disembodied voice that is seemingly narrating his life as if it were a novel. The worst part is that the voice states that Harold will soon die. Gyllenhaal played Ana, Harold's love interest.
End Of Watch (2012) - 7.6
Starring Jake Gyllenhaal and Michael Peña in its two lead roles, End of Watch is an action thriller directed by David Ayer. A critical and commercial success, the movie went on to receive several notable awards.
Gyllenhaal and Pena star as two LAPD officers working in South Los Angeles as they try to deal with a particular group of gang members.
Brokeback Mountain (2005) - 7.7
One of the best dramas of the 21st century, Ang Lee's Brokeback Mountain is remembered to this day for helping to make LGBTQ+-themed movies more mainstream and starring such big names as Jake Gyllenhaal, Heath Ledger, Anne Hathaway, and Michelle Williams.
Based on the 1997 short story of the same name, it tells the tale of two cowboys (Gyllenhaal and Ledger) who fall in love with each other as they struggle to set up their lives in 1960s-1980s American West.
Adaptation. (2002) - 7.7
An unconventional movie in many ways, Adaptation was written by Charlie Kaufman who is now known both for his screenwriting and directorial works. Maggie Gyllenhaal plays a minor role in the movie, but it is still a worthy addition to her filmography.
The story is based on Kaufman's own struggles to adapt a non-fiction book into a screenplay with Nicolas Cage playing the title role as well as Kaufman's fictitious twin brother who also wants to be a screenwriter.
Zodiac (2007) - 7.7
Though a mild success, many remember David Fincher's Zodiac for being an unusual detective mystery thriller with no killer being found in the end. It stars Jake Gyllenhaal in the lead role alongside Robert Downey Jr. and Mark Ruffalo.
Based on the real Zodiac killings of the 1960s-1970s, it focuses on a cartoonist who becomes an amateur detective as he obsessively tries to find out who the Zodiac Killer is.
October Sky (1999) - 7.8
Though somewhat forgotten nowadays, October Sky is considered one of Jake Gyllenhaal's breakthrough roles (coming out just before his other big early role in Donnie Darko).
Based on the true story and the memoir written about it, it tells the story of Homer H. Hickam Jr., who was a coal miner's son aiming to become a NASA engineer despite his father's protests.
Nightcrawler (2014) - 7.9
A huge commercial and critical success, Nightcrawler saw Jake Gyllenhaal going through one of the biggest physical transformations for a movie with the actor being almost unrecognizable with so much weight lost.
Set in Los Angeles, it follows a stringer named Lou Bloom (Gyllenhaal) who records violent events and incidents at night and then sells those recordings to a local television news station.
Donnie Darko (2001) - 8.0
As mentioned above, Donnie Darko is considered to be one of Jake Gyllenhaal's breakthrough roles, but it is also notable for also having Maggie Gyllenhaal in it starring in a minor role as her brother's character's sister.
Set in October 1988, it follows the life of a teenager named Donnie Darko who barely escapes an accident that could have ended his life. From then on, he begins seeing the so-called Frank - a strange figure in a rabbit costume who tells him about the end of the world.
Prisoners (2013) - 8.1
One of Denis Villeneuve's most well-known and successful movies, Prisoners was already notable enough for its accolades and success at the box office, but it also has a magnificent cast of Hugh Jackman, Jake Gyllenhaal, Viola Davis, Paul Dano, and others.
The story begins when two girls are abducted in Pennsylvania and local police sets out to search for them. However, they are not the only ones looking for the children - their parents are doing so too, and they are ready to use all the necessary means to find their daughters.
The Dark Knight (2008) - 9.0
Christopher Nolan may be known primarily for making deep blockbusters, but his most well-known and both critically and commercially successful movie remains The Dark Knight starring Christian Bale, Michael Caine, Heath Ledger, Gary Oldman, Aaron Eckhart, Morgan Freeman, and, of course, Maggie Gyllenhaal.
Gyllenhaal replaced Katie Holmes as Rachel Dawes. After the events of the first movie, Bruce Wayne has now become an established vigilante, but organized crime is still a reality in Gotham City. Now, Batman has to come face to face with the anarchistic Joker who seems to have appeared out of nowhere.