Thanks to a headline-grabbing livestream [1], the world is learning what theatre fans have known for a while: Jake Gyllenhaal [2] can sing! The Oscar-nominated actor blew everyone away when he and his former co-star, Tony winner Annaleigh Ashford, sang together on Take Me to the World: A Sondheim 90th Birthday Celebration on Apr. 26. The Sunday in the Park with George co-stars 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 showtunes — and he's combined it with his comedy chops [4] from time to time too. Keep reading for some of our favourite clips of Gyllenhaal singing over the years!