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Jake Gyllenhaal has famously donned a cowboy hat, combat gear, and even a bubble, but he's also missed out on a number of roles, including multiple superhero movies and a 90's classic.

Directed by David Fincher, the film explores the story about the serial killer Zodiac who stalked the Bay Area during the late 1960s and early 1970s.Even thought there is a big age gap between them, a source shared that Jeanne Cadieu is “very mature for her age.” Allegedly, Gyllenhaal and Cadieu “really took things slow, but are now pretty serious.” Despite his colorful dating history, Jake Gyllenhaal has actually never tied the knot with anyone before.In 2015, he was asked about this on Howard Stern’s radio show.He made his film debut in 1991 with a minor role in the comedy-drama City Slickers.In 1993, he appeared in A Dangerous Woman, a motion picture adaptation directed by Gyllenhaal's father Stephen Gyllenhaal and co-written by his mother Naomi Foner that was based on the novel of the same name by Mary Mc Garry Morris.

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