Popsugar Entertainment Music Watch Jake Gyllenhaal Singing Videos Please Enjoy These 9 Truly Amazing Videos of Jake Gyllenhaal Singing 28 April 2020 by Amanda Prahl Image Source: YouTube user Alvino Novea Fandy Thanks to a headline-grabbing livestream, the world is learning what theatre fans have known for a while: Jake Gyllenhaal 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 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 from time to time too. Keep reading for some of our favourite clips of Gyllenhaal singing over the years! Jake Gyllenhaal Sings "Move On" for Take Me to the World: A Sondheim 90th Birthday Celebration (Skip to around the 2:03:30 mark) 1 / 9 Jake Gyllenhaal and Annaleigh Ashford Record "Move On" 2 / 9 Jake Gyllenhaal Sings "Finishing the Hat" from Sunday in the Park with George 3 / 9 Jake Gyllenhaal Sings a Whitney Houston Parody on The Late Late Show with James Corden 4 / 9 Jake Gyllenhaal Sings "Music Everywhere" on John Mulaney & The Sack Lunch Bunch 5 / 9 Jake Gyllenhaal Sings on Saturday Night Live 6 / 9 Jake Gyllenhaal, Sean Hayes & James Corden Sing at the 2016 Tony Awards 7 / 9 Jake Gyllenhaal Sings "Maria" from West Side Story 8 / 9 Jake Gyllenhaal Sings "Putting it Together" on Popcorn with Peter Travers 9 / 9 MusicJake Gyllenhaal