Jake Gyllenhaal has famously dated Reese Witherspoon, Taylor Swift and Kirsten Dunst. Here’s a look back at his dating history.

That could very well change this year, as both Othello and Romeo and Juliet were revived this season boasting three major stars: Jake Gyllenhaal and Denzel Washington in the former, and Kit Connor ...

Toronto - The usually upbeat heartthrob Jake Gyllenhaal looked pretty serious at the premiere of his latest movie at the Toronto International Film Festival on Friday. Enemy is Gyllenhaal’s second ...

Concluding, “Where Gyllenhaal’s smile teases, his body indulges. The fight scenes in Liman’s Road House are just as bloody and ridiculous as those in Herrington’s.” ...

Jake Gyllenhaal Opens Up About His Meme-Inspiring Photo with Beyoncé and Jay Z The actor was pictured deep in court-side conversation with the power couple in 2014.

Gyllenhaal captioned the post “This role would be perfect for Jake Gyllenhaal,” accompanied by four red flag emojis, seemingly hinting (understandably) that the projects were a little eccentric.

O’Brien then noted that though Gyllenhaal keeps it old school, many of his fans are active on social media, referencing one meme account called “Jake Doing Things” that posts photos of the ...

Taylor Swift's short film All Too Well has the internet roasting Jake Gyllenhaal. Explore the funniest memes about his role in this breakup saga.

Jake Gyllenhaal was “honored” to be the host of the Season 49 finale episode of “SNL” but sorta wished he had been asked to host the premiere of Season 50.

“Prisoners” is Gyllenhaal’s second film with Denis Villeneuve, after the two worked on the upcoming “Enemy” together.