The Best Maggie Gyllenhaal Movies And How To Watch Them

Maggie Gyllenhaal in Crazy Heart
(Image credit: Fox Searchlight Pictures)

Maggie Gyllenhaal is one of the actresses who immediately makes a movie more interesting as soon as she appears on the screen. There’s a look in her eyes and a way that she carries herself that makes it so clear that she is confident in her abilities and dedicated to her craft. Over the years, she has added emotional weight to movies like The Dark Knight, brought her signature charm to the likes of Stranger Than Fiction, and even found ways to the make characters like the one in The Kindergarten Teacher seem sympathetic. Each and every one of these roles is a testament to Gyllenhaal’s innate ability to bring characters to life.

But, when discussing the best Maggie Gyllenhaal movies, you run into a problem. No, not one where you have too few titles to talk about, but the one where you have so many great performances that it’s hard to narrow it down to just 10. But we’re up to the task and have put together a rather comprehensive list of movies and how you can watch them streaming and elsewhere.

Maggie Gyllenhaal in The Dark Knight

(Image credit: Warner Bros.)

The Dark Knight (2008)

Christopher Nolan’s The Dark Knight is often considered the best live-action Batman movie, and there’s a seemingly endless list of reasons to back up this claim (you could also make an argument for it being the best comic book movie of all time). The second installment in Nolan’s grounded and ultra-popular DC Comics trilogy sees Batman (Christian Bale) facing off with his most notorious adversary, the Joker (Heath Ledger), as the Crown Prince of Crime uses the city of Gotham and its inhabitants as some sick social experiment while also testing the might and will of the Caped Crusader, exposing the hero’s dark nature in the process.

One of these tests involves Rachel Dawes (Maggie Gyllenhaal), Bruce Wayne’s childhood friend and the woman who he was willing to leave the cowl and cape behind for. Gyllenhaal’s commanding performance helps add to the dilemma Bruce faces throughout the movie as he tries to win her heart while also protecting the citizens of Gotham. You almost forget that Gyllenhaal stepped in for Katie Holmes, who departed the franchise following Batman Begins.

Stream The Dark Knight on HBO Max.
Rent/Buy The Dark Knight on Amazon.
Buy The Dark Knight on DVD/Blu-ray on Amazon.

Jeff Bridges and Maggie Gyllenhaal in Crazy Heart

(Image credit: Fox Searchlight Pictures)

Crazy Heart (2009)

In Scott Cooper’s 2009 gut-wrenching romantic drama, Crazy Heart, Maggie Gyllenhaal plays Jean Craddock, a reporter and single mother to a four-year-old son who first meets country singer Bad Blake (Jeff Bridges) when she agrees to write a story on him while he’s in Santa Fe, New Mexico, on tour. What starts out as a friendly interviewer-interviewee relationship quickly turns into a sprawling love affair with the highest of highs and lowest of lows, the latter of which are mostly due to the washed-up singer’s alcohol and commitment issues. 

One of the questions that Crazy Heart sets out to answer is how much is someone (Maggie Gyllenhaal’s character) willing to endure in order to give a person a second chance at a career, with love, and in life. Gyllenhaal’s portrayal of a headstrong woman willing to fight for what she loves earned the actress an Academy Award nomination.

Stream Crazy Heart on Hulu.
Rent/Buy Crazy Heart on Amazon.
Buy Crazy Heart on DVD/Blu-ray on Amazon.

Maggie Gyllenhaal and Jake Gyllenhaal in Donnie Darko

(Image credit: Pandora Cinema)

Donnie Darko (2001)

Despite not making any waves at the box office upon its release in late 2001, Richard Kelly’s psychological drama, Donnie Darko, has become a cult classic in the 20 years since its debut. This mind-bending thriller follows a teenage boy named Donnie Darko (Jake Gyllenhaal) after he meets a strange figure in a rabbit costume known as Frank, who leads the trouble youth through a series of tasks before the end of the world (28 days later). One of the enduring qualities of the movie is the way in which it leaves the viewer to decide if what Donnie is experiencing is reality or a delusion brought on by mental illness.

And, it’s not just Donnie Darko who goes through a series of strange and troubling events over the course of the movie, as nearly all of the characters, including his sister Elizabeth (Maggie Gyllenhaal), must overcome one obstacle or another. By the time the Donnie Darko ending comes around, each and everyone in Donnie’s life is impacted by his decisions one way or another.

Stream Donnie Darko on Tubi.
Rent/Buy Donnie Darko on Amazon.
Buy Donnie Darko on DVD/Blu-ray on Amazon.

Maggie Gyllenhaal in Stranger Than Fiction

(Image credit: Sony Pictures Releasing)

Stranger Than Fiction (2006)

Marc Foster’s 2006 dramedy Stranger Than Fiction centers on Harold Crick (Will Ferrell), a lonely IRS agent who despite being great at his job has trouble finding happiness and meaningful relationships in his personal life. However, Harold’s life is forever changed when he discovers that his day-to-day activities are being written and narrated by Karen Eiffel (Emma Thompson), a novelist suffering from severe writer’s block who is trying to find a way in which to kill the man she thinks is a fictional character. 

This eye-opening (and maddening) discovery by Harold Crick brings about a change in his outlook on life. During this time, Harold also strikes up a relationship with baker Ana Pascal (Maggie Gyllenhaal), a woman he was auditing for the IRS before getting to know her on a more personal level. But with his impending doom around the corner somewhere, Harold comes to terms with his own mortality just as Karen Eiffel begins to have second thoughts about the ending of her book.

Buy Stranger Than Fiction on DVD/Blu-ray on Amazon.

Kirsten Dunst and Maggie Gyllenhaal in Mona Lisa Smile

(Image credit: Sony Pictures Releasing)

Mona Lisa Smile (2003)

Mike Newell’s 2003 drama Mona Lisa Smile follows a group of colleges students whose lives are forever changed when Katherine Ann Watson (Julia Roberts), a young professor, begins offering an unorthodox art history course at an all-women’s private university in the early 1950s. Through the course of the semester, students like Betty Warren (Kirsten Dunst) and Giselle Levy (Maggie Gyllenahaal), who are on the opposite side of just about every argument and philosophy in life, go through enormous changes that help them better see the other side’s views and accept each other on a deeper level.

Now, this isn’t to say everything is peachy with the characters explored throughout Mona Lisa Smile, because there are tough moments that everyone — teacher and students alike — face on their own personal journeys. But, through these struggles and life lessons, they are given a new perspective on life, love, and just about everything else.

Stream Mona Lisa Smile on Starz.
Rent/Buy Mona Lisa Smile on Amazon.
Buy Mona Lisa Smile on DVD/Blu-ray on Amazon.

Nicolas Cage and Maggie Gyllenhaal in Adaptation

(Image credit: Sony Pictures Releasing)

Adaptation (2002)

The 2002 dark comedy, Adaptation, which was written by Charlie Kaufman and directed by Spike Jonze (the two previously worked together on Being John Malkovich), centers on a fictionalized version of the screenwriter (Nicolas Cage) and his twin brother Donald (also played by Nicolas Cage) as the former attempts to adapt The Orchard Thief into a screenplay while the latter finds success coming up with a formulaic action thriller. Loosely based on Kaufman’s real experience attempting to adapt the cumbersome novel years earlier, the Academy Award-winning film is a fantastical and bizarre exploration of writer’s block, anxiety, and getting fulfillment out of life.

On top of the extraordinary dual-performance by Nicolas Cage, Adaptation features a remarkable cast that includes Maggie Gyllenhaal as Donald Kaufman’s love interest Caroline Cunningham, Chris Cooper in an Oscar-winning performance as John Laroche, Brian Cox as acting coach Robert McKee, and Meryl Streep as a fictionalized version of The Orchard Thief’s author, Susan Orlean.

Stream Adaptation on Tubi.
Rent/Buy Adaptation on Amazon.
Buy Adaptation on DVD/Blu-ray on Amazon.

Maggie Gyllenhaal in Secretary

(Image credit: Lions Gate Films)

Secretary (2002)

Steven Shainberg’s 2002 erotic drama Secretary sees Maggie Gyllenhaal take on the role of Lee Holloway, a submissive young woman who works under the demanding and domineering attorney, E. Edward Grey (James Spader). What starts out as the standard employer-employee relationship slowly takes a turn toward the more sexual side as the two engage in a BSDM relationship, which turns into a twisted love affair. Not even Lee’s engagement to her fiancé Peter (Jeremy Davies) can keep her mind off the experiences she shared with Grey, causing a deep internal battle.

Maggie Gyllenhaal received a great deal of praise for her tortured performance upon the release of Secretary and was even nominated for a Golden Globe Award for her portrayal of Lee Holloway. She also took home several year-end awards from the likes of the Chicago Film Critics Association and the National Board of Review.

Stream Secretary on Showtime.
Rent/Buy Secretary on Amazon.
Buy Secretary on DVD/Blu-ray on Amazon.

Maggie Gyllenhaal in The Kindergarten Teacher

(Image credit: Netflix)

The Kindergarten Teacher (2018)

One of the best movies on Netflix, Sara Colangelo’s 2018 drama The Kindergarten Teacher (a remake of a 2014 Israeli film of the same name) centers on Lisa Spinelli (Maggie Gyllenhaal), a teacher in a bit of rut both personally and professionally whose life is given new meaning when she discovers one of her young students, Jimmy Roy (Parker Sevak), is a brilliant poet despite not being able to write them down. What starts out as a teacher helping her student reach his full potential quickly turns into an obsession, one that forces Lisa to make one unethical decision after another.

One of the more complicated of Maggie Gyllenhaal’s performances, her portrayal of a teacher who gets carried away by her obsessive nature is truly something to behold here.

Stream The Kindergarten Teacher on Netflix.

Maggie Gyllenhaal, Michael Fassbender, and Domhnall Gleeson in Frank

(Image credit: Element Pictures)

Frank (2014)

Lenny Abrahamson’s 2014 comedy Frank follows the rock-and-roll outfit known as The Soronprfbs as they start planning out their debut album. Led by the mysterious Frank (Michael Fassbender), an odd frontman who insists on wearing a giant fake head, the band deals with the normal issues up-and-comers face in their pursuit of fame and fortune, including loads and loads of personal drama.

Michael Fassbender’s take on the enigmatic Frank is made all the better thanks to the supporting cast of characters that includes The Soronprfbs’ new keyboardist Jon Burroughs (Domhnall Gleeson), and Clara Wagner (Maggie Gyllenhaal), the singer’s most trusted confidant.

Stream Frank on Magnolia Selects (Amazon Add On).
Rent/Buy Frank on Amazon.
Buy Frank on DVD/Blu-ray on Amazon.

Maggie Gyllenhaal in Paris, je t'aime

(Image credit: La Fabrique de Films)

Paris, Je T’aime (2006)

The 2006 anthology film, Paris, Je T’aime, features a collection of 18 short films, each featuring a different cast and and director, each bringing their own spin on the iconic French city. Maggie Gyllenhaal stars in “Quartier des Enfants Rouges,” a short segment in which she portrays an American actress who develops a crush on a local drug dealer who provides her with strong hash and so much more in the “City of Lights.”

Although Maggie Gyllenhaal's appearance in Paris, Je T'aime is brief, it's more than worthy of a spot on the list of her best movies.

Stream Paris, Je T’aime on Tubi.
Rent/Buy Paris, Je T’aime on Amazon.
Buy Paris, Je T’aime on DVD/Blu-ray on Amazon.

Hopefully this list helps you decide on which movie to watch when you’re looking to explore Maggie Gyllenhaal’s vast library of great film performances. But, in the event you are looking for something new to check out, take a look at CinemaBlend’s schedule of 2021 new movie releases.

Philip Sledge
Content Writer

Philip grew up in Louisiana (not New Orleans) before moving to St. Louis after graduating from Louisiana State University-Shreveport. When he's not writing about movies or television, Philip can be found being chased by his three kids, telling his dogs to stop barking at the mailman, or chatting about professional wrestling to his wife. Writing gigs with school newspapers, multiple daily newspapers, and other varied job experiences led him to this point where he actually gets to write about movies, shows, wrestling, and documentaries (which is a huge win in his eyes). If the stars properly align, he will talk about For Love Of The Game being the best baseball movie of all time.