All the times Jake Gyllenhaal did theatre

The Oscar and Tony Award nominee will star on Broadway as the cunning Iago, opposite Denzel Washington as Othello, in the classic Shakespeare drama this spring.

Suddenly, Shakespeare! Jake Gyllenhaal returns to Broadway in classic fashion this spring as the villainous Iago in a new production of Othello opposite Denzel Washington as the envious title character.

The Kenny Leon-directed revival marks the 22nd Broadway presentation of the Bard’s tragic tale of jealousy turned deadly. It will be Gyllenhaal’s fourth Broadway turn — and first time doing Shakespeare — since his debut in 2015.

While Gyllenhaal is famous for screen roles including Brokeback Mountain, which earned him an Oscar nomination, the 43-year-old Tony Award nominee has regularly returned to theatre. While we await Othello’s premiere, learn more about Gyllenhaal’s most noteworthy stage credits.

Check back for information on Othello tickets on New York Theatre Guide.

This Is Our Youth

After appearing in such movies as October Sky, Donnie Darko, and Moonlight Mile, Gyllenhaal made his theatrical debut in the 2002 London premiere of Kenneth Lonergan’s 1996 drama. He played Warren, a disaffected 19-year-old, opposite Anna Paquin and Hayden Christensen in the story set in early 1980s New York.

A Variety review hailed Gyllenhaal for nailing his character’s “mock-grandiosity” and “essential sweetness.” He earned an Evening Standard Award for Outstanding Newcomer.

If There Is I Haven’t Found It Yet

Gyllenhaal made his Off-Broadway debut in British playwright Nick Payne’s play about family dysfunction, playing the bad-boy uncle to an overweight teenage girl who’s targeted by bullies and ignored by her parents. The Hollywood Reporter's review cheered Gyllenhaal for lending “mellow charisma.”

Constellations

Gyllenhaal chose Nick Payne’s two-hander about the multiverse how the choices we make influence our lives for his Broadway debut in January 2015. He played a beekeeper opposite fellow newcomer Ruth Wilson as a quantum physicist. The plot buzzes around their romance.

“The chemistry between the two actors is genuinely touching,” New York Theatre Guide’s review reads.

Little Shop of Horrors

In this 2015 summer production, Gyllenhaal flaunted his musical theatre chops as geeky florist Seymour in Alan Menken and Howard Ashman’s offbeat and beloved musical about a man-eating plant from outer space. The production was part of Encores! at New York City Center, an annual series of rarely revived musicals.

Ellen Greene reprised the role of Audrey that she originated off Broadway in 1982 and played later in the movie. The New York Post praised Gyllenhaal as “appealingly funny and sweet.”

A separate Off-Broadway revival of Little Shop of Horrors, not involving Gyllenhaal, has been running since fall 2019.

Sunday in the Park with George

In October 2016, Gyllenhaal starred with Annaleigh Ashford in the New York City Center benefit concert performances of Stephen Sondheim and James Lapine’s 1985 Pulitzer Prize-winning musical about art. In February 2017, the actors reprised their roles on Broadway.

“Mr. Gyllenhaal’s performance of 'Finishing The Hat' alone is worth the price of admission,” New York Theatre Guide’s five-star review reads.

Sea Wall/A Life

Fathers grappling with love and loss were at the heart of these stand-alone monologues by Simon Stephens (Sea Wall, performed by Tom Sturridge) and Nick Payne (A Life, performed by Gyllenhaal), whose work once again drew Gyllenhaal back to the stage. The double bill was seen in February 2019 at The Public Theater and later that year moved to Broadway, where Gyllenhaal and Sturridge each earned a Tony nomination.

Nine Stories, a production company Gyllenhaal co-founded in 2015, mounted the show, putting Gyllenhaal up for a Best Play Tony Award as well.

Slave Play

Gyllenhaal’s taste runs from musicals to provocative dramas. Nine Stories was among the producers of Jeremy O. Harris’s drama about race, sexuality, and trauma presented twice on Broadway, in 2019 and 2021.

Follies on Saturday Night Live

Okay, Gyllenhaal didn’t really appear in a production of Stephen Sondheim and James Goldman’s musical about former showbiz performers. But while hosting Saturday Night Live in May 2024, he sang a gender-bending spoof of the Follies song “Beautiful Girls” called (what else?) “Beautiful Boys.” Bowen Yang and Kenan Thompson are among the skit's other stars.

Othello

Gyllenhaal takes his first foray into Shakespeare as the cunning Iago in Othello, in which Iago stops at nothing to undermine the successful military commander's life. The actor is preparing for his role by studying the text with a professor at Columbia University and working with an acting coach to get a handle on the text.

“It is learning another language,” Gyllenhaal told The Hollywood Reporter. Verily, we’ll be all ears – and eyes – in April 2025.

Check back for information on Othello tickets on New York Theatre Guide.