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Jake Gyllenhaal Sang His Heart Out in His SNL Finale Monologue

The Road House star rarely busts out his vocals, and he brought the house down in the last monologue before SNL 50.

By Samantha Vincenty

While Jake Gyllenhaal is best known for dramatic roles in movies like Road House, The Covenant, Nightcrawler, and Zodiac, there's also a lesser-seen musical side to the actor. A side that was on full display during Saturday Night Live's season finale on May 18, when Gyllenhaal sang his heart out alongside four cast members. Their alternate rendition of Boyz II Men's "End of the Road" was a fitting tribute to the season, and it was also a rare showcase for Gyllenhaal's vocals.

How to Watch

Watch Saturday Night Live Saturdays at 11:30/10:30c on NBC and next day on Peacock.  

Gyllenhaal's monologue (monologue-enhaal?) began with some jokes about why hosting the final episode of Season 49 is second only to the honor of hosting the premiere of Season 50. Insisting that "they really bring out the big guns to host the last episode before the big anniversary season," it soon became apparent that Gyllenhaal was grabbing a mic from out of frame.

"And I know we're all waiting for Season 50. But you know, you can't get to 50 without a little bit of 49," Gyllenhaal segued. "And we're here at the finale...The end of the road."

Jake Gyllenhaal and the cast of snl during his monologue on snl episode 1864

Jake Gyllenhaal and SNL cast sing Boyz II Men's "End of the Road"

Joined by cast members Kenan Thompson, Ego Nwodim, Punkie Johnson, and Devon Walker wearing Boyz II Men-esque cardigans, Gyllenhaal put his own spin on the 1991 classic. 

Joking that he was SNL's "first choice to host the finale...after a lot of people said no," Gyllenhaal belted, "they asked Pedro Pascal but he wasn't around / Zendaya said no 'cause she'd be out of town / Even asked Gosling to come back again — he just hosted three shows agoooo!" 

His backing chorus chimed in to create a robust melody, all wearing "49" baseball caps. 

"Although we've come to the end of the road, it's the last episode / Time to say good-bye, Season 49, you'll be 50 soon," they sang.

Jake Gyllenhaal during his monologue on snl episode 1864

Does Jake Gyllenhaal sing?  

Yes. Though not often onscreen.

In 2017, Gyllenhaal sang on stage when he co-starred with Sweeney Todd's Annaleigh Ashford in a revival of Stephen Sondheim's Sunday in the Park with George. 

He also joined James Corden in a Whitney Houston parody during a live London edition of Late Late Show in 2019, singing an alternate "Greatest Love of All."

Also in 2019, Gyllenhaal made a delightfully surreal and hilarious appearance as an eccentric character named Mr. Music in John Mulaney's John Mulaney & The Sack Lunch Bunch series.

Music really is everywhere. Watch Jake Gyllenhaal sing "End of the Road" in a tribute to SNL Season 49 above.