Sing Out, Dragtastic Jake Gyllenhaal! Five Must-See Musical Moments Starring Katie Holmes, Al Pacino & More

Jake Gyllenhaal, Paul Rudd, Katie Holmes, Al Pacino and Henry Winkler are starring in straight plays this season, but they’re not about to let the musical headliners have all the fun! These actors aren’t singers, but they’ve taken impressive (and mostly hilarious) stabs at big, Broadway-style musical numbers over the years, and these performances must be revisited. From Rudd’s impromptu Les Miz duet to Jake Gyllenhaal’s powerhouse rendition of “And I Am Telling You I’m Not Going” (in drag), find out if these celebs have what it takes to play Javert, Effie, Eponine and more.


Jake Gyllenhaal — “And I Am Telling You” (SNL)
Hollywood hunk Jake Gyllenhaal is earning rave reviews as a dysfunctional British uncle in If There Is I Haven’t Found It Yet off-Broadway—but let’s rewind back to 2006, shall we? Brokeback Mountain was the biggest film of the year, and the Academy Award nominee had just gotten hoards of new, gay fans who were dying to see him throw on a glittery gown and belt out a Broadway diva number. Ask and you shall receive! On SNL, Gyllenhaal sang a surprisingly kick-ass version of “And I Am Telling You” from Dreamgirls while a crowd of zealous cowboys looked on.
Singing: 8.9 Showmanship: 10


Paul Rudd & Jason Segel — “The Confrontation” (ABC News Now)
In 2009, Grace star Paul Rudd and his real-life pal Jason Segel starred as male BFFs in the zany comedy I Love You, Man. While doing press for their new film, ABC News Now host Peter Travers challenged the duo to sing “The Confrontation,” from Les Miserables on the spot. Although both had previously sung renditions of the song with other actors (Segel with Neil Patrick Harris and Rudd with David Wain), they had never practiced it together. Rudd channels Javert from "the English cast” while Segel was clearly modeling his performance after Colm Wilkinson. Move over, Russell and Hugh! Seriously. Move over.
Singing: 9.8 (no rehearsal!) Showmanship: 8.2


Henry Winkler — “Heartbreak Hotel” (Happy Days)
The Performers star Henry Winkler wasn't always a Broadway porn icon. Back in 1974 (way before the Broadway jukebox musical All Shook Up), WInkler took the small screen by storm as greaser and lady-killer Arthur Fonzarelli. On season three of Happy Days, the Fonz volunteers to sing “Heartbreak Hotel” at the Saturday Senior Dance, but minutes before his big number, the leather-clad tough guy gets stage fright. Although Winkler’s nervous rendition of the Elvis hit is more of a spoken-word performance, it still gets major points for creativity and making the ladies squeal.
Singing: 7 Showmanship: 9.3


Katie Holmes — “On My Own” (Dawson’s Creek)
After a highly publicized breakup with Tom Cruise, Katie Holmes is returning to Broadway in Dead Accounts this fall. But before she was TomKat, she was Joey Potter, the adorable girl-next-door on the hit series Dawson’s Creek. On one memorable 1998 episode, Joey competes in the Miss Windjammer Pageant. For the talent portion of the competition, Joey brings the house down with a tearful rendition “On My Own” from Les Miserables. Aside from an amusing mystery accent Holmes must have picked up at the Paul Rudd School of London Cast Recordings, we’re not sure what Dawson, Jen and the gang are so excited about. Meh.
Singing: 4 Showmanship: 6 Nostalgia Bonus: 10


Al Pacino — “Dunkaccino Rap” (Jack and Jill)
Remember when the movie Jack and Jill came out in 2011, starring Adam Sandler as his own sister in drag? Yeah, we didn’t see it either—and sadly, we all missed out on Al Pacino’s fantastic rap skillz! Thankfully, you don’t have to watch the whole movie to see the Glengarry Glen Ross star throw down some killer beats as Dunkaccino, the gangsta new mascot for Dunkin’ Donuts. Sing it with us! “You want creamy goodness? I’m your friend. Say hello to my chocolate blend! Attica, hoo-ah, latte light, this whole trial is out of sight!”
Rapping: 9.2 Showmanship: 9.8