Thanks to a headline-grabbing livestream [1], the world is learning what theater fans have known for a while: Jake Gyllenhaal [2] can sing! The Oscar-nominated actor blew everyone away when he and his former costar Tony-winner Annaleigh Ashford sang together on Take Me to the World: A Sondheim 90th Birthday Celebration on April 26. The Sunday in the Park With George costars teamed up for a moving duet [3] of "Move On," but it's far from the first time we've heard Gyllenhaal's impressive pipes in action. He's certainly no stranger to Sondheim songs, but he's done much more than show tunes — and he's combined it with his comedy chops [4] from time to time, too. Keep reading for some of our favorite clips of Gyllenhaal singing over the years!