You see them on a red carpet and it looks like the usual PR song and dance. Two A-list guys, expensive suits, flashing teeth. But with Hugh Jackman and Jake Gyllenhaal, something feels different. It’s less "we share the same agent" and more "we actually like grabbing a beer together."
Most people know them for that one viral photo. You know the one. Ryan Reynolds looking absolutely miserable in a bright red Christmas sweater with a giant gold bow, flanked by Jackman and Gyllenhaal laughing like they just pulled off the heist of the century. That 2018 prank wasn't just a one-off joke; it was a window into a friendship that has quietly become one of the most stable things in a town built on ego.
The Dark Roots of a Fun Friendship
It’s kinda ironic that one of the funniest public duos started in such a dark place. Back in 2013, they starred in Prisoners. If you haven’t seen it, it’s a brutal, rain-soaked thriller directed by Denis Villeneuve. Jackman plays a father whose daughter goes missing, and Gyllenhaal is Detective Loki, the twitchy cop trying to find her.
They only actually share about four scenes in the whole movie.
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Usually, when actors are barely on screen together, they don’t bond. They do their work, go to their trailers, and that’s it. But these two spent hours off-camera obsessing over the script with Villeneuve. They wanted to make those few confrontations feel heavy. Real. Honestly, that intensity forged something. Gyllenhaal has mentioned in interviews that he was "deeply inspired" by Jackman's work ethic, while Jackman basically says he loves the guy.
Beyond the "Ugly Sweater" Prank
That 2018 sweater prank—where they told Ryan Reynolds it was a themed party when it definitely wasn't—is what everyone remembers. It’s peak "friendship goals." But if you look closer, this trio is more of a chaotic brotherhood.
- The Ryan Reynolds Factor: Reynolds is the common denominator, but the Jackman/Gyllenhaal dynamic has its own flavor. It’s less about social media "feuds" and more about genuine support.
- The Foodie Bond: During the Prisoners press tour, Gyllenhaal famously teased Jackman about his eating habits. Apparently, Jackman eats "like a horse" to maintain his Wolverine physique. Jake found it hilarious. Hugh just blamed it on "worms."
- The Stage Connection: Both men are theater geeks at heart. While Jackman is the king of Broadway (The Music Man, The Boy from Oz), Gyllenhaal has carved out a massive reputation in shows like Sunday in the Park with George. They respect each other as "serious" actors who aren't afraid to look silly.
What’s Happening Now?
It’s 2026, and people are still asking when they’ll work together again. There’s been plenty of fan-made trailers for a Prisoners 2, but let’s be real: that story is done.
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However, they are both busier than ever. Jackman is currently attached to The Sheep Detectives (slated for February 2026), a comedy where he plays a shepherd whose sheep solve murders. It sounds wild. Gyllenhaal is working on Remain, a supernatural thriller with M. Night Shyamalan.
Will they ever share the screen again? Maybe. But even if they don’t, the friendship seems to be the rare Hollywood kind that doesn’t require a film contract to survive.
Why We Care So Much
Honestly, it’s probably because Hollywood feels so fake most of the time. When we see two guys who have been at the top of their game for twenty years still laughing at each other’s jokes, it’s refreshing. It’s not about "branding." It’s just Hugh and Jake.
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If you want to keep up with what they’re doing next, your best bet isn't just following their IMDB pages. Watch their social media around the holidays. If Ryan Reynolds starts looking nervous, you know Jackman and Gyllenhaal are up to something.
Next Steps to Follow the Duo:
- Revisit Prisoners: Watch it again, but focus on the four scenes they share. The chemistry is undeniable even when they are screaming at each other.
- Check the 2026 Release Calendar: Keep an eye out for The Sheep Detectives and Remain. While they aren't together, their project choices still reflect that "intense-meets-weird" energy they both love.
- Look for the SickKids Charity Work: Much of their "pranking" often circles back to Ryan Reynolds' work with the SickKids foundation. Supporting that cause is the best way to see the "sweater" making a comeback for a good reason.