5 Best Maggie Gyllenhaal Movies

The five best Maggie Gyllenhaal movies are a diverse bunch, ranging from the box office smash hit superhero movie “The Dark Knight” to the quirky, relatively obscure and highly sexual“ Secretary.” They all have one thing in common, though: one of our all-time favorite actresses.

  1. “The Dark Knight.” The sequel to Christopher Nolan’s “Batman Begins” is both one of the best Maggie Gyllenhaal movies and also the highest-grossing movie she’s been in. She took over the part of Bruce Wayne’s love interest Rachel Dawes, played in the previous film by Katie Holmes, and did a much better job at the role. Perhaps it was because she hadn’t been brainwashed by a diminutive Scientologist?
  2. “Donnie Darko.” For many people, this was their first exposure to Maggie Gyllenhaal. Despite having been in some more obscure films earlier in her life, this was the first time she starred in something with a broader audience. She played the sister of the titular Donnie in this movie, which wasn’t too far a stretch for her considering Donnie was played by her real-life younger brother Jake Gyllenhaal.
  3. “Secretary.” After Maggie’s break-out role in “Donnie Darko,” she got her first substantial lead role playing a masochistic secretary beguiled by a sadistic James Spader in this odd bit of semi-erotic cinema. This is not a movie for the kids, but it is a movie for anyone who wants to see Maggie Gyllenhaal get spanked.
  4. “Adaptation.” The only reason “Adaptation” is not higher on the list of the five best Maggie Gyllenhaal movies is that she has a relatively small part in it. It is a fantastic mind bender of a movie written by Charlie Kaufman and directed by Spike Jonze, the same duo behind the even stranger “Being John Malkovich.”
  5. “Confessions of a Dangerous Mind.” Another movie with a script by Charlie Kaufman, although this entry into the five best Maggie Gyllenhaal movies is much less of a mind trip than “Adaptation” or “Being John Malkovich.” Once again our girl Maggie has only a small part in this movie (which breaks our hearts), but it’s an entertaining movie nonetheless and certainly worth watching.
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