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  2. Jake Gyllenhaal Was Almost Cast as Owen Wilson's Character in Zoolander.

    Jake Gyllenhaal Was Almost Cast as Owen Wilson's Character in Zoolander.

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  4. Slideshow tribute to Jake Gyllenhaal.

    Slideshow tribute to Jake Gyllenhaal.

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  5. Jake Gyllenhaal says filming with Jenifer Aniston was ‘torture’

    Jake Gyllenhaal says filming with Jenifer Aniston was ‘torture’

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  7. Jake Gyllenhaal Expresses Passionate Opinion About Sean Paul

    Jake Gyllenhaal Expresses Passionate Opinion About Sean Paul

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  8. Dennis Quaid Has to Save Jake Gyllenhaal in The Day After Tomorrow #shorts

    Dennis Quaid Has to Save Jake Gyllenhaal in The Day After Tomorrow #shorts

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  9. Stephen Gyllenhaal, dad of Jake & Maggie, on his new documentary Uncharitable

    Stephen Gyllenhaal, dad of Jake & Maggie, on his new documentary Uncharitable

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  10. Jamie Foxx Pushes Jake Gyllenhaal to be a better Marine in Jarhead #shorts

    Jamie Foxx Pushes Jake Gyllenhaal to be a better Marine in Jarhead #shorts

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  11. Jake Gyllenhaal | House Tour | $8.6 Million New York Apartment, Los Angeles Mansion & More

    Jake Gyllenhaal | House Tour | $8.6 Million New York Apartment, Los Angeles Mansion & More

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  12. Jake Gyllenhaal Loved Playing Mysterio In 'Spider-Man: Far From Home'

    Jake Gyllenhaal Loved Playing Mysterio In 'Spider-Man: Far From Home'

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  13. Jake Gyllenhaal Gets a Leg Cramp While Eating Spicy Wings

    Jake Gyllenhaal Gets a Leg Cramp While Eating Spicy Wings

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  14. Jake Gyllenhaal Has Trouble At The Bar After the Spider-Man: Far From Home Premiere

    Jake Gyllenhaal Has Trouble At The Bar After the Spider-Man: Far From Home Premiere

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  15. Crocodile Attack Scene | ROAD HOUSE (2024) Jake Gyllenhaal, Movie CLIP HD

    Crocodile Attack Scene | ROAD HOUSE (2024) Jake Gyllenhaal, Movie CLIP HD

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  16. Jake Gyllenhaal | Yesterday. Today. Tonight w/ Richard Socks

    Jake Gyllenhaal | Yesterday. Today. Tonight w/ Richard Socks

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  18. Can GYLLENHAAL Be The NEXT SWAYZE?! Red 'N Red Reel Reviews ROADHOUSE

    Can GYLLENHAAL Be The NEXT SWAYZE?! Red 'N Red Reel Reviews ROADHOUSE

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  19. SouthPaw Training - Jake Gyllenhaal - Eye Of The Tiger (Remix) P.O.P EL PAPI

    SouthPaw Training - Jake Gyllenhaal - Eye Of The Tiger (Remix) P.O.P EL PAPI

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  20. Jake Gyllenhaal Wrote “The Secret Society of Aunts & Uncles” for His Nieces

    Jake Gyllenhaal Wrote “The Secret Society of Aunts & Uncles” for His Nieces

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  21. Brokeback Mountain Actor Jake Gyllenhaal Says Women are Superior to Men - More Hollywood Misandry

    Brokeback Mountain Actor Jake Gyllenhaal Says Women are Superior to Men - More Hollywood Misandry

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