Jake Gyllenhaal is the Inner-Demon Actor of his Generation 28 Mar 6:38 AM (20 days ago)
Jake Gyllenhaal could do absolutely anything next. Asked over lunch about his reading of a famed line in “Othello” — Iago’s seething “I hate the Moor” — the 44-year-old actor furrows his brow, runs his hands through his buzzed hair and ponders the performance I attended. “I’m trying to think about yesterday’s matinee, because it changes,” he says. “I’ve not made any sort of definitive choice.”
Soft-spoken and gently smiling, Gyllenhaal later summons the wide-eyed mania of his zanier characters — think his drunken “Okja” zoologist or Mr. Music of “John Mulaney & the Sack Lunch Bunch” — when the topic shifts to his eclectic body of work. “I’m just kind of random,” the Oscar nominee exclaims. “I guess as focused and intense as I can be, I also have a sense of, like, ‘That sounds fun. Oh, that scares me — I’ll give that a shot.’”
Then there’s the matter of what I should order at Via Carota, the trendy West Village osteria Gyllenhaal picked for our mid-March meetup. Having narrowed my options to the cacio e pepe and the lemon risotto, I ask Gyllenhaal for his recommendation. “You want to get both?” he gleefully responds. “You’ve got to do it. Do both. Get both!” In the spirit of impulsivity, I embrace the idea. “I mean, you’re working — you should have some joy,” Gyllenhaal says. “We have to leave you carbed up. You have a lot of typing to do.”
That carpe diem approach helped steer Gyllenhaal toward “Othello,” the blockbuster Shakespeare revival now on Broadway. Gyllenhaal was shooting “Guy Ritchie’s The Covenant” on the Spanish island of Tenerife when he fielded the offer to star as Iago opposite Denzel Washington’s titular general in the Kenny Leon-directed tragedy. A Shakespeare novice, Gyllenhaal asked to read the play and promptly bumped against Iago’s first monologue.
“I read it through twice, and I went, ‘I don’t know,’” Gyllenhaal recalls. “There were bits I understood, and I sat in this purgatory of, ‘Can I do this?’”
Still, Gyllenhaal thought about how his and Washington’s paths had run parallel for years. Gyllenhaal worked with director Antoine Fuqua, Washington’s frequent collaborator, on the films “Southpaw” and “The Guilty.” When prepping for “Southpaw’s” boxing sequences, Gyllenhaal connected with Terry Claybon, Washington’s longtime trainer, and worked out at the same gym as his fellow A-lister.
Having floated in Washington’s orbit without colliding, Gyllenhaal was eager to connect with an acting icon he had revered for decades. A pre-pandemic New York theater regular, Gyllenhaal also hadn’t starred in a play since his Tony-nominated turn in 2019’s “Sea Wall/A Life” and found himself itching to fine-tune his technique onstage.
“Am I going to forever say Kenny Leon and Denzel Washington asked me to play Iago and I said, ‘Thank you, but no’?” Gyllenhaal asks. “Also, I think it was at a time [when I was] just finding a moment to be reinspired by what it is that I do.”
Thus Gyllenhaal signed on for the production, which runs through June 8 at the Ethel Barrymore Theatre, and spent the better part of a year becoming fluent in Shakespeare. As he studied with Columbia professor James Shapiro and vocal coach Jeannette Nelson, Gyllenhaal navigated the byzantine text and found a way into Iago’s troubled headspace. That part is nothing new — whether he’s playing a hallucinating teen in “Donnie Darko,” a tragically repressed sheepherder in “Brokeback Mountain” or a ruthlessly opportunistic videographer in “Nightcrawler,” Gyllenhaal has a knack for shining light on the mind’s darkest recesses.
As much as “fearless” gets thrown around acting circles with abandon, Gyllenhaal earns the moniker. Picking projects that traverse in torment, he’s not afraid to bring a character’s inner demons to the surface. Brawny-to-scrawny transformations, vocal affectations, physical tics and trembles — Gyllenhaal stuns by fusing intense preparation with in-the-moment inspiration.
“There’s an ambition to be at his best and to push the boundaries of acting, and to try to create something that has not been seen before,” says Denis Villeneuve, who directed Gyllenhaal in the surrealist drama “Enemy” and the child-abduction thriller “Prisoners.” “He wants to try to re-create the chaos of life.”
Speaking between sips of mint tea, Gyllenhaal is not so chaotic. Mostly, he’s cordial and considered, with dashes of self-deprecation to offset the earnestness. Clocking my empty plate, Gyllenhaal serves me a helping of insalata verde between name-checking Danny Kaye, Paul Newman and Washington as his acting idols and hailing the performances of Cole Escola in “Oh, Mary!” and Audra McDonald in “Gypsy” this Broadway season.
The son of accomplished screenwriter Naomi Foner Gyllenhaal and prolific TV director Stephen Gyllenhaal, he grew up in Los Angeles’ Hancock Park neighborhood immersed in show business. As a child watching his now-Oscar-nominated older sister, Maggie, perform onstage, he instinctively wanted to emulate her. After appearing in a pair of student productions when he was 10 or 11 — playing the Pharaoh in “Joseph and the Amazing Technicolor Dreamcoat” and the Scarecrow in “The Wizard of Oz” — Gyllenhaal discovered comfort in the theater.
“The oddity, I think, of performance is that it’s so unnatural,” Gyllenhaal observes. “But I remember something feeling right about that.”
As Gyllenhaal found his way to Hollywood — making his screen debut as Billy Crystal’s son in “City Slickers” at age 10 and breaking out as NASA engineer Homer Hickam in “October Sky” at 18 — he leaned on a lesson instilled by his industrious parents: “Freedom is on the other side of discipline.” Looking back, Gyllenhaal credits his filmmaker father with gifting him a sense of cinematic wonder and his wordsmith mother with fostering his appreciation for storytelling.
“They gave me a world — I think some of it was conscious and some was unconscious — saying, ‘Look at this sacred space where you can put up all these feelings and let them out,’” Gyllenhaal says.
Actor Peter Sarsgaard had just started dating Maggie Gyllenhaal when he met Jake at a bar in the East Village more than two decades ago. Gyllenhaal naturally had questions — Sarsgaard was the guy seeing his sister, after all. Yet over the years, Gyllenhaal’s now-brother-in-law has seen that inquisitive streak endure.
“If he finds something there, then his curiosity won’t let up,” says Sarsgaard, who went on to work with Gyllenhaal on the 2005 Gulf War drama “Jarhead” and the 2024 courtroom drama series “Presumed Innocent,” among other projects. “Many good actors are people that are fervent. Onstage, you’re going back over the same thing over and over, and you have to be curious in order not to be bored out of your mind. On film, it just goes on for ages. So it really requires an unrelenting attitude.”
Boasting both leading man charm and character actor eccentricity, Gyllenhaal has often gravitated toward the obsessive. Lou Bloom, the unnervingly mannered stringer he played in 2014’s “Nightcrawler,” is a man of unhinged ambition. Georges Seurat, the post-impressionist painter Gyllenhaal portrayed in the 2017 Broadway revival of “Sunday in the Park With George,” is all about artistic perfection. In David Fincher’s 2007 fact-based procedural “Zodiac,” he played a cartoonist consumed by his pursuit of a serial killer. Gyllenhaal’s twitchy detective in 2013’s “Prisoners” is similarly driven by justice.
They’re all focused characters inhabited by a focused actor. But consider Gyllenhaal’s performances in the apocalyptic blockbuster “The Day After Tomorrow,” the $100 million rom-com “Love & Other Drugs” and the Marvel romp “Spider-Man: Far From Home,” and it’s clear he can also have a good time in a box office darling. Amid such widely seen projects — not to mention feverish public interest in his dating history — Gyllenhaal adopted a mantra of keeping his personal life personal.
“Being a famous person has, obviously, its great pros, but it also has its great cons,” says Andrew Burnap, the Tony winner who plays Cassio in “Othello.” “I think he, in his life, is very aware of that, and his commitment is to just being a great artist.”
That dedication to craft extends to playing the guitar, honing his photography and learning French. (“Jake constantly mocked me about the way I speak English,” Villeneuve says with a laugh, “and he took the risk of trying to learn French.”) A passionate cook, he tends to take charge of the Gyllenhaal-Sarsgaard household’s Thanksgiving feast. (“He’s just coming over with hot plates and things through the door,” Sarsgaard says. “It’s wonderful.”) Last fall, Gyllenhaal and Sarsgaard met with celebrity chef Hugh Fearnley-Whittingstall at his River Cottage estate in Devon, England; Gyllenhaal calls it “probably the highlight of my year.”
“I like the practice of cooking because it’s a constant discovery and experience,” Gyllenhaal says. “Maybe it’s the love of interpretation.”
Gyllenhaal’s interpretation of Iago, the Machiavellian underling previously played by the likes of Kenneth Branagh, Daniel Craig, Mark Rylance, Christopher Walken and Ian McKellen, earned raves when reviews for “Othello” dropped Sunday night. Although the overall production drew a mixed critical reception, its $2.8 million week during previews was the highest-grossing for a play in Broadway history, not accounting for inflation. (Last week, the George Clooney-starring “Good Night and Good Luck” bested that mark.)
Described by Washington Post theater critic Naveen Kumar as “the production’s indisputable anchor,” Gyllenhaal stalks the stage with the air of a men’s-rights provocateur in Leon’s 2028-set revival. Soon after Iago spits “Be a man!” to one pawn, Gyllenhaal lays bare the pain of a villain whose famously inscrutable motivations seem to veer, in this iteration, toward feeling underappreciated by Othello.
“Jake is special because he’s in pursuit of truth, and he does it on such a deep level,” says the director Leon. “It’s not someone twirling their mustache, and it’s not somebody playing an evil guy. This is somebody who has found the humanity in the most obvious of villains.”
Before Iago undoes Othello, the antagonist reveals his deceitful intentions during a celebrated soliloquy. It was during this speech — at the March 19 matinee, at least — that Gyllenhaal delivered the line “I hate the Moor” not with the cold calculation of many an Iago before but tortured conflict.
“It’s the age-old story,” explains Gyllenhaal, whose commitment to the character included a Venetian makeover of his dressing room. “It’s Steinbeck-ian. It’s siblings. It’s family. It’s being human. It’s the voice in our head that tells us ‘you can’t do that’ or ‘don’t do that’ or ‘you’re not capable of that.’ I think Iago is also hurt, and you can’t forget that.
“The argument he makes to himself is laying groundwork for something he needs to be true. Because I think he loves the Moor. When he says, ‘My lord, you know I love you,’ I don’t think that’s some manipulative thing in my choice. And I do love Denzel, so I can’t not play that.”
It’s a zig when the audience might expect a zag from an actor who showcased a sly, cunning side as the Spider-Man baddie Mysterio and that stealthily monstrous “Nightcrawler” character. Having read Martha Stout’s “The Sociopath Next Door” when preparing for “Nightcrawler,” Gyllenhaal decided against portraying Iago with comparable callousness. Still, finding his Iago’s empathetic tenor was a process that spilled well into previews.
“I was playing it pretty aggressively early on,” Gyllenhaal says. “The words themselves, if you enunciate them sometimes too much, if you don’t go back and give them speed and also space and grace, they become very evil.”
More than once, Gyllenhaal cuts himself off and cautions that he could ramble all day about his onstage process. For all of his on-screen successes, his fixated mind takes particular pleasure in finding ways to intrigue, unsettle or enchant a theater audience.
“Sometimes people come from a career in TV and film and it takes a minute for them to navigate a different medium,” says Annaleigh Ashford, Gyllenhaal’s “Sunday in the Park” co-star. “But it’s part of his marrow. He’s so at home onstage. He is so gifted at the give-and-take with the audience, the communion that you share with the living, breathing people that are sitting there watching you.”
While Gyllenhaal has booked his next two starring roles — a supernatural M. Night Shyamalan flick and a sequel to 2024’s “Road House” remake — he’s already kicking around ideas for a return to the theater. “The feeling I get before I go out every night is no different from the kid in high school on that stage,” he says. “The wings still look the same. The intensity is still the same. It may be Broadway, but the joy is the same.”
When I bring up the idea of an overarching trajectory, he chuckles, circles back to spontaneity and answers the question with one of his own: “Have you discovered that I clearly have no idea?”
Gallery Link:
Photoshoots & Outtakes > Portraits > The Washington Post
Shubert Foundation’s 11th Annual High School Theatre Festival 26 Mar 6:08 AM (22 days ago)
Jake hosted the Shubert Foundation’s 11th Annual High School Theatre Festival on Monday (March 24th), at the Shubert Theatre in New York City. Photos from the event have been added to the gallery.
Gallery Link:
Public Appearances > 2025 > Shubert Foundation’s 11th Annual High School Theatre Festival
Visiting Jake Gyllenhaal in His ‘Othello’ Dressing Room 25 Mar 6:00 AM (23 days ago)
First there was method acting (sometimes it wins you an Emmy, sometimes it bristles your costars, sometimes it does both). Then a novel phenomenon called method dressing took red carpets by storm (remember Zendaya’s perfectly executed tennis-themed looks for her Challengers press tour?) Next up: The method dressing room.
Othello star Jake Gyllenhaal’s backstage home-away-from-home in Broadway’s Barrymore theater is an extension of the Shakespearean world he’s been steeped in while developing his version of Iago, the duplicitous ensign to the titular Venetian army general played by Denzel Washington. The revival is a modern take on The Bard’s centuries-old tragedy with relatively spare set design, so Gyllenhaal’s dressing room presented an opportunity to bring the narrative to life with more evocative decor.
“I was told that it’s the dressing room that Marlon Brando was in for A Streetcar Named Desire.
It has hundreds of layers of paint from every performer that has had or shared that room, and so it holds within it a deep, rich history that I am honored to be a part of and to add to, even if it’s temporary,” Gyllenhaal tells AD.
The BAFTA winner has a soft spot for design, evidenced by his role as an ambassador for the luxury Italian porcelain purveyor Ginori 1735, so, naturally, he was inclined toward an elevated approach for the short-term dwelling.
To make the most of his time in such hallowed quarters, Gyllenhaal brought in designers Ruby Kean and Lisa Jones of Atelier LK, a firm operating out of New York and London. Kean says the trio agreed upon a vision for the room that was “narrative-driven, but also something that would be very comfortable for him that he could really retreat into,” given the demanding, high-pressure environment of a Broadway production. Another consensus was highlighting local creatives with their decorative choices. Gyllenhaal’s “love for artisan craftsmanship, as well as emerging designers in New York, was quite a key thing for Ruby and I to explore,” Jones says.
A handmade chess set by NYC-based designer Minjae Kim serves as a stylish callout to the calculated gameplay characteristic of Iago, whose plotline is defined by his meticulous orchestration of Othello’s downfall. Pulled up to the board are a pair of chairs also by Kim—one light, one dark—that echo the aesthetic of the chessboard itself while aligning with the themes of racial dichotomy underpinning the tale.
Subtlety, though, was key. Kean explains the team was cognizant of staying grounded and mindful about “capturing the world of Othello in a way that didn’t feel too overly literal.” Accessories woven throughout the dressing room reference the play in a more understated manner, but conjuring the appropriately dark and dramatic vibe to match Othello led to an emphasis on sourcing the right lighting. Two ochre sconces of Venetian Murano glass (made by New York designer Dana Arbib), Sophie Lou Jacobsen’s Tulipa pendant in a moody tobacco shade, and a prickly Crown of Thorns lamp by Wretched Flowers offer Gyllenhaal “the ability to be flexible with the lighting,” per Kean. “It’s warm yet elegant. It’s comforting, but it has a sense of formality to it, and I love that they’ve really tried to make it feel like the spaces I’ve been to in Venice,” Gyllenhaal says of the sultry lighting.
The more nuanced nods to the Italian locale in which the play opens are balanced with a statement-making, theatrical approach to the room’s walls, which set the scene via Rafa Prieto x Wallpaper Projects photographs of Venice blown up large. The dressing room is “a very small and intimate space, and we really wanted it to take on the charm and romanticism of the play,” Kean says. Two immersive images taken in the city lend themselves to distinctively separate moods in their respective vignettes. A shot of a salmon-hued façade along Salizada dei Spechieri tonally encourages “people to gather, feel energized, to learn lines—making more of an uplifting, lighter space,” Jones says. A more low-key ambiance takes shape in the room’s back area. Jones explains that a wall wrapped in the image of a café table with a dim, low-down view of the canal was chosen with the intent of helping Gyllenhaal “unwind, relax, take a moment to rest, and to feel a little bit more like a downtime space.”
Of course, there hasn’t been much downtime of late. “Denzel’s made his way up there a couple of times, but just through the nature of him being the general, I tend to go to his room. The rest of the cast comes in and out. At this point, we’re all so focused. It’s quite a piece to try and do service to, so we’re all onstage all the time rehearsing when we’re not in the play,” Gyllenhaal says. “When time comes and we’re in our run and we get to come in at 5:00 or 6:00 for an 8:00 p.m. show, I hope we’ll hang out there a lot more.”
Othello starring Denzel Washington and Jake Gyllenhaal officially opens March 23 at the Ethel Barrymore Theatre and runs through June 8.
Gallery Link:
Theater Productions > Othello (2025) > Dressing Room Photoshoot for Architectural Digest
The Late Show With Stephen Colbert (Videos + Screencaps) 25 Mar 3:59 AM (23 days ago)
Jake stopped by The Late Show with Stephen Colbert last night to promote ‘Othello’. Follow the link to watch the interview, or download the videos in our media section. Screen captures are in the gallery.
Gallery Link:
Screen Captures > Television > Publicity Shows > The Late Show With Stephen Colbert
‘Othello’ Opening Night In New York City 23 Mar 4:00 PM (24 days ago)
Opening night of ‘Othello’ took place last night at the Barrymore Theatre in NYC. Photos of Jake during the curtain call, backstage with his family, greeting former president Joe Biden with the cast after the show, and at the after party have been added to our gallery. ‘Othello’ runs from now through June 8th. Get tickets here!
Gallery Links:
Public Appearances > 2025 > ‘Othello’ Opening Night – Curtain Call
Public Appearances > 2025 > ‘Othello’ Opening Night – Backstage
Public Appearances > 2025 > ‘Othello’ Opening Night – After Party
Denzel & Jake On Bringing A Powerhouse ‘Othello’ To Broadway 27 Feb 9:54 AM (last month)
We’re talking about faith. Last December, just before Christmas, actor Denzel Washington was baptized and licensed as a minister, and so it hasn’t taken long, chatting about his return to Broadway playing the title role in Othello, for conversation to turn to matters of belief. Not religious, per se; Shakespeare’s great tragedy turns on themes of love and jealousy and betrayal. Perhaps, Othello’s choice to trust the evidence of his eyes—a planted handkerchief—over his innocent wife Desdemona’s protests that she has never strayed, is a kind of loss of faith, a misguided embrace of rationality over spirit.
“Well, sure, he wants proof,” pipes up Jake Gyllenhaal, who co-stars in the production as Iago, planter of the aforementioned handkerchief, “and, Iago keeps leading him back to the handkerchief—look, look!—but the only reason he can manipulate Othello that way is that they have a bond. They’ve fought together, trusted each other with their lives. He knows this is a man with a great sense of faith and love.”
“Mm-hm,” adds Washington. Meanwhile, he’s picked up a thick binder and is flicking through it. We’re in a small midtown office a few minutes’ walk from the Barrymore Theatre, where the two actors will be performing in Othello through June 8—one of the starriest outings in what is shaping up to be a very starry Broadway season. In an hour or so, the pair is due at the theater for a meeting with the play’s director, Broadway veteran Kenny Leon, who staged a revival of Our Town at the Barrymore just last fall. Rain is pelting down outside as we chat, and Gyllenhaal seems to be keeping half an eye on it as he continues ruminating. “But Iago also knows, Desdemona—that’s something new for Othello. Which makes him vulnerable.”
“He’s not experienced putting all his cards on the table for one woman,” Washington chimes in, still focused on his binder.
“He’s been at war,” adds Gyllenhaal.
“Seven years of war,” adds Washington, citing the play. “So that’s his biography, right there. That’s where he’s comfortable. Battle.”
I feel like I’m in college. I say so. Gyllenhaal laughs. “This is what we do. It’s the best—going around and around, trying to figure out, who are these people? What makes them do what they do?”
“Ah!” Washington holds up his binder. He’s found what he was looking for: a page from his notes on the script, with a line of Othello’s scrawled in all caps: if she be false, heaven mocks itself. He flashes his iconic megawatt smile. “Talking about faith—that’s actually the first thing I wrote down,” he says. Then, from under his ballcap, he fixes me with an ardent gaze and says the line aloud, falling into character. “If she be false, O, then heaven mocks itself! I’ll not believe it!” I don’t feel like I’m in college anymore. A different, dreamier smile plays over Washington’s face as he quotes from elsewhere in the play. “For know Iago, but that I love the gentle Desdemona…”
Returning to himself, Washington grins, forms a finger pistol and aims it at Gyllenhaal. “Learning my lines! Finally catching up with this guy!”
In a manner of speaking, Gyllenhaal started learning his Iago lines seven months before rehearsals for Othello began in New York. “I’d never done Shakespeare,” he explains. “And you get that call and it’s, not only do I want to do this, I have to do this. But honestly, I didn’t know: can I do it? It scared me.”
Thus Gyllenhaal embarked on a five-day-a-week, two or three-hour-a-day Shakespeare training regimen not entirely dissimilar, I suggest to him, from the process of getting into fighting form for, say, Road House. “Sort of…” he assents, somewhat skeptical of the analogy. “You’re learning a language. And that top layer of, ‘what does this mean?’ you can get through pretty fast, but then the words, they’re so intense, what he’s actually saying—you can get lost in them. And the only thing I’m concerned about,” Gyllenhaal continues, “is being present and able to listen to one of greatest actors ever when we’re onstage.”
“And I’m seven months behind,” quips Washington, who—at time of writing, a week before opening night of previews—still wasn’t off-book.
“But you’re used to this, the words don’t get in your way,” notes Gyllenhaal. He glances over at me, then turns back toward Washington, gazing at him with not a little wonder. “He can say his lines like, you know, like they’re just coming out of his mouth…” Great acting, Gyllenhaal will later remark, is often a matter of doing as near as possible to nothing.
“Sometimes you’ll have this sort of explosion of inspiration from the word when you hear it,” says Gyllenhaal. “And sometimes you keep it as simple as you possibly can.”
“Well,” Washington offers with a shrug. “sometimes the line is just Shakespeare’s version of ‘get out of here.’”
For Washington, Othello is a homecoming. And a reunion. Twenty years ago, he played Brutus in a lauded Broadway production of Julius Caesar; his itch to do more Shakespeare wasn’t satisfied by his turn playing the title role in Joel Coen’s 2021 film The Tragedy of Macbeth. In the interim, Washington had struck up a fruitful collaboration with director Leon, with whom he’d worked on the Broadway plays Fences and A Raisin in the Sun. It so happened that Leon was fresh off mounting a production of Hamlet for Shakespeare in the Park—only his second staging of the Bard, after winning the 2020 Obie for his direction of Much Ado About Nothing—when Washington got it into his head to take a fresh crack at Othello, a part he first played half a century ago, as a 20-year-old drama student.
“I’ll tell you exactly what happened, we were doing Gladiator, and the young boy’s down on the Coliseum floor doing all the fighting,” Washington recalls, referring to the recent sequel starring Paul Mescal. “And all us old senators are sitting around in our gowns with our pinkies up, we’re extras basically, just talking, and someone brings up Othello. And I’m like, oh man, I wish, but I’m too old now. And one of the other senators says to me, no, no, no, go back and read the play…”
In the popular imagination, the ‘Other’-ness of “the Moor,” as Othello is often called, boils down to race. Yet as Washington points out, lines in the play suggest that the peculiarity of his marriage to Desdemona has as much to with age—she is young, whereas Iago refers to Othello as “an old black ram,” and Othello describes himself as having “declined into the vale of years.” (We don’t think about the age thing so much because Othello is so often played by vigorous men in the prime of life—to wit, James Earl Jones, long synonymous with the part, was 33 when he won an Obie for his performance in Joseph Papp’s 1964 production in Central Park.) Class is also a factor: Othello is an ex-slave-turned-soldier who has worked his way up, on the strength of his formidable talents, to a high-ranking military position; Desdemona is the daughter of a powerful politician in Venice, where the play is set. She’s sheltered; Othello is a man of the world.
Leon leaned into this last contrast with his casting, plucking a virtual unknown, 30-year-old Molly Osborne, to play opposite Washington, an actor who has surpassed mere celebrity to become one of the greatest leading men ever produced by Hollywood. “It’s surreal,” says Osborne, who’d been bouncing around the English theater scene for about a decade before she finally booked a West End show—Fiddler on the Roof directed by Trevor Nunn—and started the dominoes falling that ended with Leon hopping a flight to London to meet her in person. “That’s what they say, right? It only takes one part, and then you’re off,” Osborne says with a laugh, before going on to admit she was not expecting career takeoff, in her case, to lead her more or less straight into the arms of Denzel Washington. “It’s an honor just to be in the room. But you can’t just be awestruck—you have to do your job and be a good scene partner.”
Of course, being a little awestruck helps, when depicting someone in love. At the start of the play, Othello and Desdemona are utterly dazzled by each other. A question raised by the play is: why? Theirs is a pairing so out of the ordinary, it seems to demand to be justified. “We’re still finding it,” says Osborne. “Kenny’s re-named rehearsal ‘discovery,’ which I love, and that’s what we’ve been doing, discovering aspects of their relationship. Like, we know Othello’s told her all about his life—and in modern terms, maybe she’s the first person who’s really, you know, held him with that, held his trauma. It’s very pure. She sees his pain as part of what makes him beautiful. But maybe that also means she’s in denial of his darkness.”
As is common these days, Leon has time-shifted Othello out of Renaissance-era Venice and Cyprus. His version is set in 2028, and Othello and his troops are an occupying force of U.S. Marines—a battle-hardened band of brothers that find themselves suddenly, and as Gyllenhaal points out, dangerously idle. “You train these guys for combat, they go on mission after mission, then they’re waiting around, they’ve got nine months off—where are they going to put the target?”
“I wanted Jake because I knew he was going to search for the truth in the character,” says Leon. “I wanted humanity, not some mustache-twirling villain.” If ever a role tempted such a portrayal, it would be Iago, who Samuel Taylor Coleridge famously described as a “motiveless malignancy.” He schemes to destroy Othello, and drives him half-mad, and—spoiler alert—brings out Othello’s murder of his beloved wife, and his own eventual suicide, and again you wonder—why? Racism? Resentment about being passed over for promotion? Sheer boredom? No explanation is sufficient.
“I’m not sure I even understand what I’m doing, in the sense that, OK, Iago starts a ball rolling, but then it’s rolling faster and faster, and he has to start making choices that maybe he doesn’t even believe in, but there’s just no way back,” says Gyllenhaal. “Or that’s one interpretation.”
Another: the person Iago is actually trying to destroy is Desdemona, because that’s how he gets his beloved general, his Othello, back. “You talk about faith, and you talk about love, and really it’s heartbreaking, because I do believe that Iago loves Othello, deeply,” Gyllenhaal continues. “Admires him.”
“At war, these two men, it was like they were one person,” Washington interjects.
“And then they get to Venice and he meets Desdemona and I’m losing it,” Gyllenhaal concludes.
“It’s easy to say Othello is gullible,” adds Washington. “No, no, no—he trusts this man more than he trusts anyone in the world. He trusts him with his life.”
If love is a conspiracy of two, impenetrable to outsiders, Iago finds a way to pierce through, seeding doubt about Desdemona in Othello. In so doing, he establishes a competing conspiracy, and the men draw closer. “I am your own forever,” Iago vows in Act III, marriage-like. The play doesn’t work if Othello and Iago don’t read as authentically intimate. Judging by the easy rapport between Washington and Gyllenhaal, they won’t struggle to find that camaraderie onstage.
“We’ve been asking ourselves, who was Othello, who was Iago before the wars? Because we’re trying to understand, you know, what here is what war’s done to them, versus what’s their actual essence?” says Washington.
“That’s a part of the play that speaks directly to today,” he goes on. “You send these men and these women out to fight for freedom, they’re going to come back changed. PTSD. Something. They’ve got scars.”
There’s a simple logic behind Leon’s choice to set the play in 2028, rather than the here-and-now: he’s aiming for resonance, not “relevance.” “This is a play about the struggles of all time,” he says. “The struggle to be a human—to love, to trust, to be curious, to grow, to heal, all of that; take away everything except what makes us naked, pure human beings, that’s how people can find themselves in this story.” What Leon hopes to avert is Othello being pinned down, butterfly-like, to a political position, or forced onto one side or another in this country’s seemingly never-ending culture wars. It will be hard to avoid—the moment is fraught; the play has an interracial couple at its heart; what is racism, if not a “motiveless malignancy?” People will chew on the Broadway first of an Othello directed and lead-produced by black men—Leon and Brian Anthony Moreland, respectively—and cut their assumptions about that to fit their pre-existing views. But becoming grist for hot takes is very much not the point. “When Denzel came to me a year-and-a-half ago and said, I’ve got free time in 2025, we didn’t know who’d be sitting in the Oval Office, we didn’t know what’d be in the news—and it didn’t matter,” notes Leon. “Shakespeare wrote this play more than four hundred years ago. This is about our time on the planet.”
And anyway, there’s something about Othello that rebuffs reduction. When I chat with Molly Osborne, for example, she mentions that she and Leon imagine Desdemona as the daughter of a prominent American political dynasty—“and she’s rejecting all that.” But almost immediately upon saying this, Osborne doubles back, and adds, “there’s more to their love, of course; it’s not explainable. It’s just—love is love.”
Washington echoes this syntax when he details what Leon is seeking from his actors’ performances. “No pinkies up, no ‘Shakespearean acting,’ I don’t even know what that is. You think that’s what people were like four hundred years ago? You think that’s how they went around the corner to get coffee? No,” Washington posits, shaking his head. “Just truth. And the truth is the truth. That’s what Kenny says, the truth is the truth.” And knowing when you’ve touched that is matter not of mind, but of feeling—of faith, you might even say. A surrender to the sublime mysteries of the human heart.
“I keep watching him, thinking, how do I do that? Because it’s not as simple as ‘keep it simple,’” Gyllenhaal says, peering at Washington. “And then the answer is just—be great. That’s it, be great.”
Washington breaks into a belly laugh, wags a finger at Gyllenhaal. “Look at you, ready for opening night…you’re Iago-ing me already.”
Gallery Link:
Photoshoots & Outtakes > Sessions > Photoshoots From 2025 > Session 1 [Vogue]
‘Othello’ Photocall In New York 9 Feb 6:10 PM (2 months ago)
Jake Gyllenhaal joined Denzel Washington and other cast / crew today at a ‘Othello’ photocall / press day in NY. Several interviews with Jake and Denzel from press day have also been added to our video archive.
Gallery Link:
Public Appearances > 2025 > ‘Othello’ Photocall In New York
Jake To Star In New Film From M. Night Shyamalan, Nicholas Sparks 29 Jan 1:24 PM (2 months ago)
M. Night Shyamalan looks to have his sights set on his next mysterious project and looks to have found some high-profile talent to collaborate with. Sources tell Deadline Jake Gyllenhaal is set to star in M. Night Shyamalan’s upcoming film, a supernatural romantic thriller, based on an original story co-created by Shyamalan and global-bestselling novelist Nicholas Sparks. Shyamalan and Sparks are independently writing a screenplay and a novel, respectively, based on the same original love story.
Both projects will be based on the same concept and set of characters, but tailored to their respective mediums. For Shyamalan not only does he land another A-lister to lead his family as so many are always looking to work with him, this also marks the first time he will collaborate with a high-profile writer on an idea, something to surely excite fans of the master storyteller.
Shyamalan and Ashwin Rajan will produce through Blinding Edge Pictures, alongside Sparks’ longtime producing partner Theresa Park and Marc Bienstock. Sparks is Executive Producer. Shyamalan’s Blinding Edge Pictures will produce the film, which is in discussions with WB for theatrical release.
For Gyllenhaal, this follows a stellar year that started with his hit reinvention of the classic action pic Road House at Amazon MGM Studios. The film was a massive hit for the studio breaking streaming records with a sequel already in development. He followed that up with the critically acclaimed limited series Presumed Innocent for Apple TV+, another hit that earned him a Golden Globe nomination. This year he will share the stage starting next month with Denzel Washington in an adaptation of Othello on Broadway.
Shyamalan has captured the attention of audiences around the world for almost two decades, creating films that have amassed more than $3 billion worldwide as he is coming off another summer hit with his thriller Trap starring Josh Hartnett.
Sparks is one of the world’s most beloved storytellers. All of his books have been New York Times best-sellers, with over 130 million copies sold worldwide, in more than 50 languages, including over 92 million copies in the United States alone. His latest novel, Counting Miracles, released this fall and debuted at #1 on the NY Times best-sellers list. It will be adapted into a film by Amazon.
82nd Annual Golden Globe Awards 5 Jan 8:41 PM (3 months ago)
Jake Gyllenhaal and his girlfriend Jeanne Cadieu attended the 82nd Annual Golden Globe Awards yesterday at the Beverly Hilton in Beverly Hills, CA. Pictures from the event have been added to the gallery. Clips from the red carpet, as well as audience shots during the telecast, have also been added to our video archive.
Gallery Links:
Public Appearances > 2025 > 82nd Annual Golden Globe Awards
Photoshoots & Outtakes > Portraits > 82nd Annual Golden Globe Awards – Cartier Portraits
Happy 44th Birthday, Jake Gyllenhaal! 19 Dec 2024 3:56 AM (3 months ago)
We here at IHeartJake.com want to wish Jake Gyllenhaal a Happy 44th Birthday! In honor of Jake’s birthday, I’ve added 6 new ‘Stronger’ portraits from the 2017 Toronto Film Festival to the gallery. Enjoy!
Gallery Link:
Photoshoots & Outtakes > Portraits > ‘Stronger’ Portraits – Toronto Film Festival