Jake Gyllenhaal and Jimmy take turns guessing what song the other is singing while wearing noise-cancelling headphones.

Gyllenhaal got more passionate about his performance as the monologue went on, singing, “They asked Pedro Pascal, but he wasn’t around. Zendaya said no ‘cause she’d be out of town.

In case you forgot that Jake Gyllenhaal can sing, he provided a delightful reminder on "The Kelly Clarkson Show" on April 21. The actor went head to head with Kelly Clarkson for a game called ...

Taylor Swift makes over $12 million singing about Jake Gyllenhaal Swift and Jake Gyllenhaal dated briefly in 2010. She's earned $12.3 million on hits like "All Too Well" and "I Bet You Think About ...

Jake Gyllenhaal hosted the season finale of 'SNL,' with his opening monologue laying the groundwork for the show's upcoming historic 50th season.

Jake Gyllenhaal and his girlfriend Jeanne Cadieu stepped out for the New York premiere of his upcoming Prime Video movie 'Road House.' The actor was joined by his parents.

Jamie Lee Curtis got to see firsthand what Jake Gyllenhaal’s skills were outside of his dazzling acting abilities. He made a lot of sourdough bread, a lot. So singing, acting, sourdough.