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25 of the sweetest friendships between male celebrities that have stood the test of time

Gabbi Shaw   

25 of the sweetest friendships between male celebrities that have stood the test of time
Jon Stewart and Stephen Colbert have been friends for decades.Scott Kowalchyk/CBS/Getty Images
  • These 25 long-lasting friendships are so strong that not even Hollywood can break them.
  • Some pairs met on set, while others came up in the entertainment industry at around the same time.
  • Mel Brooks and Carl Reiner were friends for 70 years, and still ate dinner together every night until Reiner's death in June.

Hollywood feuds are notorious — it's not an easy place to make real, lasting friendships. But these guys all prove that some friendships can go the distance and last decades.

Some have more of a mentor/mentee vibe, like Jake Gyllenhaal and Tom Holland or Bryan Cranston and Aaron Paul, while others are total equals who started together, like Matt Damon and Ben Affleck. But what they all have in common is real love for each other.

Keep scrolling to see 25 of the most iconic and beloved friendships between male celebrities.

Ben Affleck and Matt Damon became friends when they were kids. Now, they're producing partners, Oscar-winning screenwriters, and, remarkably, still friends.

Ben Affleck and Matt Damon became friends when they were kids. Now, they
Matt Damon and Ben Affleck in 2017.      Frazer Harrison/Getty Images

Hollywood can be a fickle place, but these two have remained friends from childhood throughout their two-plus decades in show business, The two burst onto the scene as co-stars and co-screenwriters in 1997's "Good Will Hunting," and Affleck, at 25, became the youngest person to ever win Best Screenplay at the Oscars.

"I've known him for 35 years, and we grew up together. We were both in love with the same thing — acting and filmmaking. I think we fed on each other's obsession during really formative, important years and that bonded us for life," said Damon in 2016.

The two are set to reunite on screen in 2021's "The Last Duel."

George Clooney and Brad Pitt frequently prank each other.

George Clooney and Brad Pitt frequently prank each other.
Brad Pitt and George Clooney in 2012.      Kevin Mazur/WireImage/Getty Images

Clooney and Pitt became close friends on the set of "Ocean's Eleven," and have worked together multiple times since, including the two "Ocean's" sequels, as well as "Burn After Reading," and "Confessions of a Dangerous Mind."

Famously, the two engage in prank wars on set. "I've done some terrible things to Brad and Brad's done some terrible things to me too," Clooney said in a 2015 appearance on "The Graham Norton Show."

Zach Braff and Donald Faison remained friends after "Scrubs," and they even host a podcast about the show now.

Zach Braff and Donald Faison remained friends after "Scrubs," and they even host a podcast about the show now.
Donald Faison and Zach Braff in 2014.      Bruce Glikas/FilmMagic/Getty Images

For nine years, the two played iconic TV best friends JD and Turk on "Scrubs," though, as we know, just because you play best friends on TV doesn't mean you get along in real life. These two, however, are the real deal.

"It has to be real. The only way to have a real bromance is if you're genuinely fond of each other. [Zach]'s my best friend. I'm really fond of that man, I'm not ashamed to say it. And to the supporters of our bromance, I'd like to say, thank you," Faison said in 2016.

In 2020, the two started their own podcast about "Scrubs" called "Fake Doctors, Real Friends With Zach + Donald."

Patrick Stewart and Ian McKellen have been friends for 20 years.

Patrick Stewart and Ian McKellen have been friends for 20 years.
Ian McKellen and Patrick Stewart in 2020.      Eamonn M. McCormack/Getty Images

Though they are two of the most beloved British actors of their generation, the two didn't become friends until they both starred in 2000's "X-Men" as enemies. Stewart played the noble Professor X, while McKellen took on the mantle of Magneto, an iconic Marvel villain (or misunderstood anti-hero, depending on your point of view).

"We had adjoining trailers. On those kind of movies, you spend more time sitting in your trailer than you do in front of the camera. So, Ian and I hung out together, drinking tea — and maybe in the afternoon, something a little stronger — and we got to know one another," Stewart told the Hollywood Reporter in 2020. "And the charm of it was that we found that we had so much in common. And by the way, he married us, my wife and me. He performed the ceremony."

Just this month, McKellen surprised Stewart for his 80th birthday by performing a sonnet for Stewart's #ASonnetADay project. "A very happy birthday, dear Patrick. Lots of love, Ian," he ended his sweet message.

Leonardo DiCaprio and Tobey Maguire have been friends since childhood.

Leonardo DiCaprio and Tobey Maguire have been friends since childhood.
Leonardo DiCaprio and Tobey Maguire in 2017.      Victor Boyko/Getty Images for LDC Foundation

DiCaprio and Maguire met when they were both 12 years old going out for the same commercials.

"I literally jumped out of the car. 'I was like, 'Tobey! Tobey! Hey! Hey!' And he was like, 'Oh, yeah — I know you. You're ... that guy.' But I just made him my pal. When I want someone to be my friend, I just make them my friend," DiCaprio said of the beginning of their friendship in 2014.

In addition to DiCaprio being named the godfather of one of Maguire's children, the two collaborated together in the 2013 adaptation of "The Great Gatsby," in which DiCaprio plays Gatsby, and Maguire plays his only friend, Nick.

"Every project we do, we talk about," said DiCaprio in 2013. "Every single choice I've made, I've talked to Tobey about and vice versa. We've had endless conversations about certain projects and argued with one another and supported one another along the way."

Tom Holland and Jake Gyllenhaal spent a lot of time together during the "Spider-Man: Far From Home" press tour, much to everyone's delight.

Tom Holland and Jake Gyllenhaal spent a lot of time together during the "Spider-Man: Far From Home" press tour, much to everyone
Tom Holland and Jake Gyllenhaal in 2019.      Woohae Cho/Getty Images

These two met when they began shooting the "Spider-Man" sequel two years ago, when they played on-screen adversaries. However, off-screen, they couldn't be anymore effusive towards each other.

"It's a romance. I'm really sick of people calling it a bromance. It's a romance. It's a legitimate romance," Gyllenhaal told Rotten Tomatoes.

Holland confirmed this — "Between me and Jake? It's full-on in love. We're getting married," he told Access Hollywood.

Even a year after the film, they're still close. In April, Holland posted a video of the two's trip to Mexico for a panel on Instagram with the caption, "Missing my husband."

Hugh Jackman and Ryan Reynolds expertly troll each other on Instagram.

Hugh Jackman and Ryan Reynolds expertly troll each other on Instagram.
Ryan Reynolds and Hugh Jackman in 2009.      Kevin Winter/Getty Images

In 2009, Reynolds and Jackman became friends on the set of "X-Men Origins: Wolverine," in which Reynolds played Deadpool for the first time (though not the same iteration that he'd play again later).

The two almost constantly troll each other on social media and in real life. Case in point: Jackman invited Reynolds to a Christmas party, but faked him out and told him it was an ugly sweater party.

Most recently, Jackman took an opportunity to both express gratitude for his Emmy nomination and roast his friend. "Lots of texts from everyone I know, nothing from Ryan. But Blake [Lively] … Hang on, I'm just reading it now. 'He's devastated. He says he's not getting out of bed for three days. This is the greatest gift you've ever given me,'" he joked.

Kevin Hart and Dwayne Johnson love to make fun of each other, but it's all from a place of love.

Kevin Hart and Dwayne Johnson love to make fun of each other, but it
Kevin Hart and Dwayne Johnson in 2019.      Albert L. Ortega/Getty Images

Hart and Johnson have starred in three movies together: "Central Intelligence," "Jumanji: Welcome to the Jungle," and "Jumanji: The Next Level." After their first film, Johnson noted that the two became fast friends.

"Since working with him I can honestly tell you that I've never had this type of brotherly chemistry with anyone that I've worked with and it's a cool thing," Johnson said in 2016.

Hart added, "There's a substance, there's life and there's values and that's what I think we respect the most about each other where the friendship is really going."

In 2019, on an episode of "Jimmy Kimmel Live!," Johnson confirmed the friendship had leveled up. He called Hart "one of my best friends," and said, "It's a real friendship, it was one that I didn't anticipate. Especially as you kind of get older in life, it's not like in high school or college where you just have like a lot of best friends. No, he has become truly a great, great friend."

Matthew McConaughey and Woody Harrelson have been friends for decades.

Matthew McConaughey and Woody Harrelson have been friends for decades.
Woody Harrelson and Matthew McConaughey in 2018.      David M. Benett/Dave Benett/Getty Images

Although they're now most famous for the critically acclaimed first season of "True Detective," it wasn't the first time this duo worked together. Their first collaboration was 1999's "EDtv." They co-starred again in 2008's "Surfer, Dude."

"One of the things where [Woody] and I are good at [in] comedy is where I start and he ends and he starts and I end and we really get on a similar frequency and roll with it," said McConaughey in 2014.

Perhaps their shared Texas heritage gave them an unbreakable bond.

Keegan-Michael Key and Jordan Peele are hands-down one of the funniest duos of all time.

Keegan-Michael Key and Jordan Peele are hands-down one of the funniest duos of all time.
Keegan-Michael Key and Jordan Peele in 2016.      Jason LaVeris/FilmMagic/Getty Images

Key and Peele worked together for five seasons on their Comedy Central series, aptly titled "Key & Peele." They even earned a Peabody Award for their work together.

While they don't work together on the show anymore, they still make the time to collaborate. After "Key & Peele" ended in 2015, they produced and co-starred in the 2016 action comedy film "Keanu," and appeared as the cute duo of Ducky and Bunny in "Toy Story 4."

When Peele won his first Oscar for Best Original Screenplay for "Get Out," photos emerged of Key's adorably joyous reaction. Soon after, he tweeted his congratulations: "Congrats to my partner in laughs @JordanPeele on his first Oscar. #oscarssopeele."

Oscar Isaac's son called Pedro Pascal "Tío Pedro" (Uncle Pedro).

Oscar Isaac
Pedro Pascal and Oscar Isaac in 2019.      Astrid Stawiarz/Getty Images for Netflix

Pascal and Isaac have been friends since at least the beginning of the decade, as evidenced by this tweet. As Remezcla has pointed out, the two have had multiple sweet moments over the decade, including a video they did for Wired, an Instagram post in which Pascal calls Isaac the love of his life, and a post from Isaac's wife that calls Pascal, Tío Pedro.

We have Isaac to thank for Pascal's role in "The Mandalorian." "Oscar was very much the voice of, 'Make sure it works out.' He played a part in making me feel certain about what I was joining," Pascal told Elle.

Dylan O'Brien and Tyler Posey became best friends after playing on-screen besties in "Teen Wolf."

Dylan O
STyler Posey and Dylan O'Brien in 2017.      Rich Polk/Getty Images for IMDb

Both got their "big breaks" when they booked the roles of Scott McCall and Stiles Stilinski on MTV's "Teen Wolf," and stayed close throughout the show's six seasons. They even lived together for the show's first two years.

"He is like my brother," Posey said of O'Brien in 2015. "Dylan, he just sits and listens, and when there's nothing to say, we just sit in silence and he's just there for me. He's a great guy. He's family," he told BuzzFeed.

Even though their "Teen Wolf" days are behind them, the two are still close. In 2018, they went to Comic Con together.

"It was our first time we went without any obligations because 'Teen Wolf' is over, so we didn't have anything to promote and we went and partied and danced all night until five in the morning," Posey said.

Blake Shelton and Adam Levine's friendship helped make "The View" the juggernaut that it is today.

Blake Shelton and Adam Levine
Adam Levine and Blake Shelton.      Trae Patton/NBCU Photo Bank/NBCUniversal/Getty Images

Shelton and Levine, both former People's Sexiest Men Alive, thank you very much, joined "The Voice" in the first season and their chemistry kept viewers coming back for years. Though Levine left the show rather unceremoniously, the two are still friends after sitting together for 16 seasons.

"It sucks not having Adam on the show. He's been there since the beginning, and it's hard not to have somebody that stupid to make fun of. Everybody here now, they're more talented, and he's not here to kick around," Shelton jokingly told Access in 2019.

He added, "We talk. We never have lost contact. Literally last week ... I was at home in Oklahoma, by myself, and we ended up FaceTiming each other for 45 minutes, just nonsense talk."

Jason Momoa and Henry Cavill have taken their friendship to superhuman heights.

Jason Momoa and Henry Cavill have taken their friendship to superhuman heights.
Jason Momoa and Henry Cavill in 2016.      David M. Benett/Dave Benett/WireImage/Getty Images

Momoa and Cavill became close on the set of "Justice League," when they played Aquaman and Superman, respectively.

When Momoa's solo "Aquaman" film was released, Cavill hilariously supported his buddy on Instagram by hanging out in some type of body of water holding a fork (like Aquaman's trident). "Channeling the man of the hour, the man of big hugs, big laughs and big pints of Guinness, my man Jason Momoa. How'd I do," Cavill wrote.

"Seriously though, I just finally got the chance to watch Aquaman here in Hungary. Jason, James and everyone involved in that movie, smashes it out of the (water)park. If you haven't seen it yet, go check it out. Jason, love you bro, you crushed it," he continued.

Vin Diesel and Paul Walker were so close that Diesel named his daughter after Walker.

Vin Diesel and Paul Walker were so close that Diesel named his daughter after Walker.
Vin Diesel and Paul Walker in 2011.      Peter Wafzig/Getty Images

The actors met on the set of the very first "Fast and Furious" movie way back in 2001, and their chemistry was unmistakable even then. After Walker's death in 2013, Diesel and the rest of the cast had to continue filming "Furious 7," which ends with a heart-wrenching tribute to Walker and Diesel's friendship.

"The day after the tragedy, for me to fly from Atlanta that night and to show up at his mother's house and for me to say to his mother, 'I'm sorry, I'm sorry, I'm sorry,' and for his mother to say to me, 'I'm sorry, I'm sorry, I'm sorry' — I said, 'Why? Why are you saying sorry to me?' And she said, 'Because you lost your other half,'" Diesel said in 2017.

Diesel named his third daughter, who was born in 2015, Pauline to pay tribute to his friend. Diesel's kids and Meadow Walker, Paul's daughter, are still friends to this day.

Mel Brooks and Carl Reiner ate dinner together nightly for years, up until Reiner's death in 2020.

Mel Brooks and Carl Reiner ate dinner together nightly for years, up until Reiner
Mel Brooks and Carl Reiner in 2014.      David Livingston/Getty Images

Brooks and Reiner, two comedic giants, were friends for 70 years. They became friends in the '50s, and became famous due to their comedic routine, "The 2,000 Year Old Man."

Just a few months before Reiner's death at the age of 98, Brooks and Reiner were profiled by the Guardian, during which they shared the secrets of their friendship and living a long and happy life, which included eating dinner together every night and watching "Jeopardy!"

"I don't think I've ever had a better friend than Carl," said Brooks.

"My God, the thought of being without him — the world would be too bleak!" Reiner added.

When Reiner died in June, Brooks' tribute was among the many. "I loved him," he wrote on Twitter. "So whether he wrote or performed or he was just your best friend — nobody could do it better. He'll be greatly missed. A tired cliché in times like this, but in Carl Reiner's case it's absolutely true. He will be greatly missed," he continued.

Stephen Colbert and Jon Stewart have compared themselves to Frodo and Sam from "Lord of the Rings."

Stephen Colbert and Jon Stewart have compared themselves to Frodo and Sam from "Lord of the Rings."
Stephen Colbert and Jon Stewart in 2019.      Scott Kowalchyk/CBS/Getty Images

For a while there, Stewart and Colbert were the reigning kings of Comedy Central. Colbert got his start on "The Daily Show" while Stewart was the host, and then moved to his own show, "The Colbert Report." Their shows ended in 2015 and 2014, respectively.

When Stewart signed off on his final "Daily Show" episode after 16 years on the air, it wouldn't have been complete without Colbert making one final appearance. "You can't possibly leave without saying goodbye to your Sam," Colbert said while grasping Stewart's hand.

"We owe you, because we learned from you," Colbert continued, in a touching, unscripted speech that surprised Stewart and moved him to tears. "We learned from you, by example, how to do a show with intention, how to work with clarity, how to treat people with respect. You are infuriatingly good at your job, and all of us who were lucky enough to work with you ... for 16 years are better at our jobs because we got to watch you do yours — and we are better people for having known you."

Justin Timberlake and Jimmy Fallon always get the giggles around each other.

Justin Timberlake and Jimmy Fallon always get the giggles around each other.
Jimmy Fallon and Justin Timberlake in 2013.      Rick Diamond/Getty Images for MTV

Timberlake and Fallon met 18 years ago at the 2002 MTV Video Music Awards, and they have been friends ever since. After that, they collaborated on a now-famous "SNL" sketch, "The Barry Gibb Talk Show," in which the two play the Gibb brothers. It's recurred multiple times throughout the years, including when the duo hosted "SNL" together in 2013.

When Fallon was named one of Time's Most Influential People, also in 2013, none other than Timberlake penned the essay. "Jimmy's lightning wit — mixed with a kindness you don't normally find in comedy — is what makes you feel so comfortable having him in your home every night," he wrote.

Their friendship came full circle when Fallon presented Timberlake with the MTV Video Vanguard Award at the 2013 VMAs — the same award show they met at over a decade prior.

Rob Schneider, David Spade, Chris Rock, and Adam Sandler are one of the most famous groups of friends "SNL" ever saw.

Rob Schneider, David Spade, Chris Rock, and Adam Sandler are one of the most famous groups of friends "SNL" ever saw.
Rob Schneider, David Spade, Chris Rock, and Adam Sandler in 2010.      Charles Eshelman/FilmMagic/Getty Images

All four joined "SNL" during the same season in 1990, and almost instantly became inseparable, along with the late great Chris Farley. Over the years, they've all collaborated in various combinations — most frequently Schneider and Sandler. In 2010, they all came together once again to star in "Grown Ups." All but Schneider returned for "Grown Ups 2" in 2013 (Schneider had scheduling conflicts and his wife was pregnant).

When Sandler returned to "SNL" in 2019 to host, he and Rock commiserated on stage about getting fired back in the '90s.

Channing Tatum and Jonah Hill made five movies together in five years.

Channing Tatum and Jonah Hill made five movies together in five years.
Jonah Hill and Channing Tatum in 2018.      Taylor Hill/WireImage/Getty Images

The two played best friends in "21" and "22 Jump Street," of course, but they also both appeared in "The Lego Movie," "This Is The End," and "Hail Caesar!"

When Hill was given the Innovator in Film Award from the Wall Street Journal Magazine, Tatum was on hand to present it to his friend.

Hill expressed his gratitude on Instagram, writing, "My old friend [Tatum] flew in to give me this award. I don't get to see him nearly as much as I'd like to and that sucks. But the idea that he would take the time out to give me this and be there for me, made me feel a feeling of friendship and joy that reminds you how special life can be. It's not about anything besides the beautiful people you meet along the way. And one of the best there is, is [Tatum]. Love u [sic] buddy."

Taika Waititi and Chris Hemsworth built a strong bond after working together on "Thor: Ragnarok."

Taika Waititi and Chris Hemsworth built a strong bond after working together on "Thor: Ragnarok."
Taika Waititi and Chris Hemsworth in 2017.      Alberto E. Rodriguez/Getty Images for Disney

Hemsworth and Waititi's natural chemistry was on full display when Waititi played the scene-stealing rock alien, Korg, in "Ragnarok," which he also directed.

"He's insanely fun," Hemsworth told GQ in 2020. "But don't mistake that child-like, frantic energy for someone who isn't prepared. That's quite a unique combination, that he has the ability to, through humour, put you at ease, but is also armed with all the knowledge that a director needs to lead you through the process."

Their working relationship is so strong that the two are teaming up again for "Thor: Love and Thunder," which Waititi will write and direct this time.

William Shatner and Leonard Nimoy were friends for 50 years. Shatner even wrote a book about their friendship.

William Shatner and Leonard Nimoy were friends for 50 years. Shatner even wrote a book about their friendship.
Leonard Nimoy and William Shatner in 2009.      Mark Davis/Getty Images

Besides being part of one of the greatest duos of all time, "Star Trek's" Kirk and Spock, the two were very close for decades. Nimoy was even the best man at one of Shatner's weddings.

Though the two weren't on speaking terms at the time of Nimoy's death in 2015, he clearly still had great affection for his late friend. On Twitter, he called him "Intelligent, insightful, just a precious gem of a man," and called him the best dad and "an amazing uncle to my daughters."

In 2016, Shatner published "Leonard: My Fifty-Year Friendship with a Remarkable Man."

Paul Wesley and Ian Somerhalder played brothers on "The Vampire Diaries," but in real life, they're just best friends.

Paul Wesley and Ian Somerhalder played brothers on "The Vampire Diaries," but in real life, they
Paul Wesley and Ian Somerhalder in 2016.      Matt Winkelmeyer/Getty Images

Arguably, the real love story at the heart of "The Vampire Diaries" was the relationship between Stefan (Wesley) and Damon (Somerhalder), and the reason it was so compelling to watch the Salvatore brothers was because of the palpable bond that the two have in real life.

"We love each other. We have wanted to kill each other about 800 times. But that means brothers," said Somerhalder in 2020, three years after "TVD" went off the air.

In fact, their friendship is so strong that the two have teamed up again, this time to create their own bourbon brand, appropriately named Brother's Bond Bourbon.

Paul Newman and Robert Redford became friends on the set of 1969's "Butch Cassidy and the Sundance Kid."

Paul Newman and Robert Redford became friends on the set of 1969
Paul Newman and Robert Redford in 2004.      Evan Agostini/Getty Images

The two Hollywood legends played the iconic duo in 1969, and their friendship lasted all the way until Newman's death in 2008. "It was just that connection of playing those characters and the fun of it that really began the relationship. And then once the film started, once we went forward, we then discovered other similarities that just multiplied over time, a common ground that we both had between us, interests and so forth, and differences," Redford told ABC in 2008.

The two even lived a mile away from each other in Connecticut for years.

"He was a real friend and that humor that we had, I'll miss that. I'll miss him," Redford said after Newman's death.

They're not the only ones to create their own alcohol — "Breaking Bad" co-stars Bryan Cranston and Aaron Paul have their own line of Mezcal.

They
Bryan Cranston and Aaron Paul in 2013.      Mark Davis/Getty Images

Though their characters, Walt and Jesse, weren't always on the same side, Cranston and Paul are very close friends in real life.

"The moment I met Bryan, I instantly fell in love with the man," Paul said at Cranston's Walk of Fame ceremony. "I mean, how could you not? He's charming, he's brilliant, and he's a beautiful human being inside and out who is constantly running around in his underwear making people laugh ... I'm here to tell you all that I, personally, would not be the same without this man."

In July 2019, the pair announced Dos Hombres Mezcal. "Three years ago we sat in a sushi bar in New York. Talking about life and what we could possibly do down the road together. We had the time of our lives while shooting 'Breaking Bad' and truly built a very special bond," the two actors wrote on Instagram.

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