If You Didn't Know Jake Gyllenhaal Could Sing, You Definitely Know Now

Updated on May 2, 2020 at 5:35 PM

Thanks to a headline-grabbing livestream, the world is learning what theater fans have known for a while: Jake Gyllenhaal 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 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 from time to time, too. Keep reading for some of our favorite 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.

Jake Gyllenhaal and Annaleigh Ashford Record "Move On"

Jake Gyllenhaal Sings "Finishing the Hat" From Sunday in the Park With George

Celebrity

Fashion

Fitness

Beauty

Love

Family

Shop

If You Didn't Know Jake Gyllenhaal Could Sing, You Definitely Know Now

Jake Gyllenhaal Sings "Move On" For Take Me to the World: A Sondheim 90th Birthday Celebration

Jake Gyllenhaal and Annaleigh Ashford Record "Move On"

Jake Gyllenhaal Sings "Finishing the Hat" From Sunday in the Park With George

Jake Gyllenhaal Sings a Whitney Houston Parody on The Late Late Show With James Corden

Jake Gyllenhaal Sings "Music Everywhere" on John Mulaney & the Sack Lunch Bunch

Jake Gyllenhaal Sings on Saturday Night Live

Jake Gyllenhaal, Sean Hayes, and James Corden Sing at the 2016 Tony Awards

Jake Gyllenhaal Sings "Maria" From West Side Story

Jake Gyllenhaal Sings "Putting It Together" on Popcorn With Peter Travers

Related

Fabrizio Copano Is Using Comedy to Address Political Wounds

For Mental Health Awareness Month, we asked Latine comedians and creators we admire how comedy has supported them in overcoming trauma and confronting life's most significant challenges.

Gina Brillon: The Loss of My Grandmother Pushed Me to Pursue Comedy

Gina Brillon is a Puerto Rican actress, stand-up comedian, writer, and mom born and raised in the Bronx.

Sasha Merci: How Comedy Has Helped Me Navigate Depression

For Mental Health Awareness Month, we asked Latine comedians and creators we admire how comedy has supported them in overcoming trauma and confronting life's most significant challenges.

Ian Lara: Comedy Gave Me the Strength to Overcome My Mother's Death

Ian Lara is a Dominican American stand-up comedian from Queens, NY, who found internet success after his appearance on "Comedy Central Stand-Up Featuring," which has garnered over 10 million views.

Willow Smith Used Meditation and Workouts to Fuel the Creativity on "Empathogen"

Willow Smith's "b i g f e e l i n g s" is the final song on her new album, "empathogen."

Nicki Nicole Says Rap Music Helped Her Get Out of Her Shell

It's a drizzly Thursday afternoon in New York City, and Nicki Nicole has spent most of her day answering back-to-back interview questions from journalists.

Revisiting Jennifer Lopez’s 2011 Album “Love?” and What It Signifies Today

As the anniversary of Jennifer Lopez's sixth studio album "Love?" approaches, it's a fitting time to reflect on this album's significance within J Lo's career, its impact on fans, and its continued relevance in light of her recent endeavors.

Thalia's "A Mucha Honra" Album Is a Love Letter to Música Mexicana

Throughout her illustrious career, Thalia has proudly represented Mexican culture through her music, iconic looks, and unforgettable performances.

Chuwi Is the Voice of a New Puerto Rican Generation

With a bassy voice and over a minimalist syncopated beat, Wilfredo "Willy" Aldarondo sings of lament.

Camila Mendes on Why We Need More Latine Representation in Rom-Coms

A simple Google search of "the best rom-coms of all time" will take you down a nostalgic hole of '90s and early-'00s movies like "10 Things I Hate About You," "While You Were Sleeping," and "P.S.

Saraciea Fennell: "The Black Girl Survives in This One" Is the Representation I Didn't See in Horror Books

I've always been obsessed with horror.

Selena Quintanilla Deserves to Be Celebrated This Year — Not Exploited

Fifty-three years ago today, the world was blessed with the birth of Selena Quintanilla-Pérez, who became an eternal icon in Latin pop culture and music.