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  1. 21 titles. Sort by List order. 1. City Slickers. 1991 1h 53m PG-13. 6.8 (63K) Rate. 70 Metascore. On the verge of turning 40, an unhappy Manhattan yuppie is roped into joining his two friends on a cattle drive in the southwest. Director Ron Underwood Stars Billy Crystal Jack Palance Daniel Stern. 2. Donnie Darko. 2001 1h 53m R. 8.0 (854K) Rate.

  2. 30 titles. Sort by List order. 1. City Slickers. 1991 1h 53m PG-13. 6.8 (63K) Rate. 70 Metascore. On the verge of turning 40, an unhappy Manhattan yuppie is roped into joining his two friends on a cattle drive in the southwest. Director Ron Underwood Stars Billy Crystal Jack Palance Daniel Stern. 2. A Dangerous Woman. 1993 1h 42m R. 5.7 (2.1K)

  3. Jake Gyllenhaal is an American actor and producer who has appeared in over 35 motion pictures (including some yet to be released), three television programs, one commercial, and four music videos. He made his film debut in 1991 with a minor role in the comedy-drama City Slickers. [1]

  4. See Jake Gyllenhaal full list of movies and tv shows from their career. Find where to watch Jake Gyllenhaal's latest movies and tv shows.

  5. 19 titles. Sort by List order. 1. October Sky. 1999 1h 48m PG. 7.8 (98K) Rate. 71 Metascore. The true story of Homer Hickam, a coal miner's son who was inspired by the first Sputnik launch to take up rocketry against his father's wishes. Director Joe Johnston Stars Jake Gyllenhaal Chris Cooper Laura Dern. 2. Donnie Darko. 2001 1h 53m R. 8.0 (854K)

  6. Find out the best and worst films of Jake Gyllenhaal according to critics' ratings. See the list of 11 movies from his career, including Certified Fresh hits like Nightcrawler, Brokeback Mountain, and Spider-Man: Far From Home.

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  8. He began acting as a child, making his acting debut in City Slickers (1991), followed by roles in his father's films A Dangerous Woman (1993) and Homegrown (1998). His breakthrough roles were as Homer Hickam in October Sky (1999) and as a psychologically troubled teenager in Donnie Darko (2001).