It was 2018 when the internet collectively lost its mind over a photo of Ryan Reynolds looking absolutely miserable in a velvet Christmas sweater. Standing on either side of him, grinning like kids who just got away with a heist, were Jake Gyllenhaal and Hugh Jackman. That single image basically cemented their status as the most chaotic trio in Hollywood.
But if you look past the Instagram trolling and the "Best Friends Day" roasts, the relationship between Gyllenhaal and Jackman is actually rooted in something much heavier. They aren't just guys who share a publicist or a love for expensive coffee.
They are two actors who survived one of the most grueling film sets of the 2010s.
The Dark Roots of the Gyllenhaal-Jackman Bond
Most people forget that before the memes, there was Prisoners.
Released in 2013 and directed by Denis Villeneuve, the movie is a relentless, stomach-churning thriller about a father (Jackman) who kidnaps and tortures the man he believes took his daughter. Gyllenhaal plays Detective Loki, a twitchy, blinking cop who is desperately trying to solve the case before Jackman’s character goes too far.
It wasn't a fun shoot.
Jackman has talked openly about how intense the role was, often staying in a state of high-octane rage and grief for weeks. Gyllenhaal, meanwhile, was doing his own thing—creating a character with strange facial tics and a mysterious backstory that wasn't even in the script. Honestly, it could have been a disaster. You have two lead actors with completely different styles, working on a story that feels like a punch to the gut.
Instead, they clicked.
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"I loved working with Jake," Jackman told reporters during the Toronto International Film Festival premiere. He mentioned that despite their characters being "lone wolves" who only share about four or five scenes, they spent hours rehearsing just to make those brief interactions feel lived-in.
They weren't just "being professional." They were building a foundation.
Why the "Third Wheel" Dynamic Works
You can't talk about Jake Gyllenhaal and Hugh Jackman without mentioning the Deadpool in the room: Ryan Reynolds.
The dynamic shifted in late 2018. Gyllenhaal had just finished Spider-Man: Far From Home, and suddenly he was everywhere with Reynolds and Jackman. This created a weird, brilliant triangle of "A-list trolling."
But there’s a nuance here that fans often miss.
While Reynolds and Jackman have that long-running, faux-feud based on their X-Men Origins: Wolverine days, Gyllenhaal’s role is more of the instigator. He’s the guy who jumped into a decades-long friendship and immediately started picking sides.
- The Christmas Sweater Prank: This is the gold standard. Gyllenhaal and Jackman told Reynolds it was a themed party. It wasn't. Reynolds showed up in a giant bow; they showed up in t-shirts.
- Best Friends Day 2019: Reynolds posted a photo with Jackman. Jackman posted a photo with Reynolds. Gyllenhaal posted a photo with Jackman and captioned it: "Happy #BestFriendsDay to Ryan Reynolds (not pictured)."
It’s high-school behavior from men in their 40s and 50s. And we love it.
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The Professional Fallout Rumors (And Why They’re Likely Wrong)
Around 2021, the internet started doing what it does best: speculating about a "falling out."
People on Reddit pointed to a 2017 WIRED Autocomplete Interview where the vibe between Gyllenhaal and Reynolds felt a bit... off. Critics called it "insufferable" or "egotistical." Then, when Gyllenhaal wasn't seen as much with the "Hugh-Ryan" duo for a year or two, the rumors of professional jealousy started flying.
Was Gyllenhaal annoyed that he hadn't reached the same "box office titan" status? Was there a bidding war over a production right?
Basically, it's all noise.
The reality is that Gyllenhaal’s career path is just different. While Jackman is out here doing Deadpool & Wolverine and massive musical revivals, Gyllenhaal has stayed in the "prestige indie with a side of blockbuster" lane. He’s producing contenders. He’s doing Road House remakes.
Friendships in Hollywood aren't always about being photographed at the same party. Sometimes it's just about two guys who respect each other's craft enough to leave each other alone for a few years.
Where They Stand in 2026
As of early 2026, both actors are busier than ever, but their paths are still crossing in spirit.
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Jackman is currently riding the wave of his most recent "final" return to the screen, and he’s slated for the upcoming Amazon MGM project The Sheep Detectives. It’s a bit of a departure, but it fits his "charming but intense" brand.
Gyllenhaal is still the king of the unexpected. Between his production company Nine Stories and his own acting slate, he’s focused on high-concept thrillers that remind everyone why Prisoners worked in the first place.
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If you're a fan trying to figure out which Hollywood friendships are real and which are "PR-mandated," look at the history.
- Shared Trauma (The Film Set Version): Actors who work on emotionally draining films like Prisoners usually either never speak again or become incredibly close. There is no middle ground.
- The "Roast" Factor: Real friends in the industry don't just post glowing tributes. They make fun of each other's height (like Reynolds claiming Jackman is under 5 feet tall) or their career choices.
- Longevity Over Visibility: The fact that Jake Gyllenhaal and Hugh Jackman don't need to be seen together every week to maintain their "brand" is actually the biggest sign that the friendship is legitimate.
Next time you see a fan-made trailer for Prisoners 2 (which, let’s be honest, will probably never happen), remember that the real sequel is just these two guys occasionally popping up on each other's feeds to ruin Ryan Reynolds' day.
That’s a much better story anyway.
If you want to keep up with their latest moves, keep an eye on the 2026 release calendars. Jackman has The Sheep Detectives coming to wide release soon, and Gyllenhaal’s production slate for this year is looking just as dense and complicated as one of Detective Loki’s mazes.