"Ben Affleck and Matt Damon are childhood friends...This is their first Academy Award."
So intoned the announcer at the 1998 Oscars as the boisterous pair, still looking like a couple of kids from the neighborhood at 25 and 27, headed to the stage to accept their win for Best Original Screenplay for Good Will Hunting—the film they decided to write together in between auditions to give themselves the sort of material that interested them as actors.
"We're just really two young guys who were fortunate enough to be involved with a lot of great people," Affleck gushed excitedly as they dissolved into their thank-yous, with extra-special shout-outs to their mothers (both in the audience), Damon's dad and the city of Boston. "There's no way we're doing this in less than 20 seconds."
Twenty-five years later, Affleck and Damon are still in business—literally, they started their own studio—and are having more fun working with each other than ever.
Talking to E! News at the premiere of their new movie Air, based on the true story of how Nike courted future NBA superstar Michael Jordan to sign with the company's then-fledgling basketball division, Affleck called directing Damon "the joy of my professional life."
Damon, turning 53 Oct. 8, joked Affleck's been directing him "for 40 years," but to do so in this official capacity was "really exciting. It was the best summer job I ever had."
Affleck, 51, echoed the sentiment: "If you're lucky, you can find a way to work with people that you love and then, as they say, you never work another day in your life."
Happily, the April release of Air—the first offering from their new shingle, Artists Equity—was just the beginning of the work they plan to do together. And it's the latest chapter of what's proved to be a beautiful friendship, one that started in Cambridge, Mass., when Affleck was 8 and Damon 10 and their families lived just a few streets away from each other.
"I think we're pretty similar," Affleck told ABC News in 2017. "People treat us differently than they used to and respond differently, 'cause they've seen us in movies and in the public sphere. But, I think about Matt and I growing up together and the time we spent together, and the time we spend together now, it's like... I don't think we've changed that much."
At the time they were even neighbors again.
"Last night he just emailed me and was like, 'Come over and watch Monday Night Football,'" Affleck shared, "and I was like [miming messaging back], 'I'm in New York, I can't come by.' But, you know, we still have that 'you want to come over to my house' kind of thing, which is a great thing, to have a friendship like that to carry you through the strange process of fame and making movies, and all that."
Affleck was born in Berkeley, Calif., before mom Chris and dad Tim (who divorced in the early '80s) moved him back East, where younger brother Casey Affleck was born in 1975. Damon, a native son of the Bay State, lived with parents Kent and Nancy and older brother Kyle.
"My mother is a professor of early childhood development, and she knew Ben's mother—who's a teacher of little kids—and sought her out after we moved back to Cambridge," Damon told Interview magazine in 1997, quipping, "so I was pretty much forced into hanging out with Ben."
Affleck said he remembered Damon as "gregarious, outgoing." So, he added, "It was no surprise that he grew up into the totally obnoxious guy he is now. Number one, he claims that I never struck him out in Little League. Which is total bulls--t—I was the best pitcher in the league."
They bonded over baseball and, eventually, acting—which Affleck started doing professionally as a kid and initially didn't have anyone to talk to about it outside of his family until his buddy took an interest.
"Matt gave acting a framework, an integration into the social hierarchy at school," Affleck, who made his movie debut at 13 in the 1981 drama The Dark End of the Street, told Parade in 2007. "As a teenager, the natural thing is to have friends who have common interests and so you fit together seamlessly. Before Matt, I was by myself. Acting was a solo activity where I'd just goof and do something, act in a little TV show or something, and no one understood it."
"None of the other kids knew what it was I did, how it worked, or anything," he continued. "All of a sudden I had this friend, Matt, and he gets it and wants to do it and thinks it's interesting and wants to talk about it. Soon both of us are doing it."
Affleck continued, "When we were teenagers, like Matt was 16 and I was 14, we'd go together down to New York City [to audition]. We'd take the train. Or sometimes we'd even take the airplane, back when there was the Eastern Shuttle or People's Express. It cost like $20 to fly and you could smoke on the plane. We were smoking like idiots because we thought we were really supposed to be grown up. It was pitiful."
Moreover, Damon told Interview, "We used to have what we called 'business lunches' in high school, which meant we met at the smaller cafeteria and got a table..." Affleck chimed in, "And worked out some business plans. We were really nerdy. So right now we'd like to skip ahead to these slightly cooler years. Otherwise this is going to get progressively embarrassing."
Damon graduated from high school in 1988 and enrolled at nearby Harvard, but two years later Affleck headed to the University of Vermont, "because I had a kind of unrequited love for this high school girlfriend," Ben explained to Parade. "She wasn't even at the university but at another school nearby. But I thought if I went to a school near her, just maybe…I was really remedial about girls in so many ways. Interestingly, there are some parallels for things to come in my life."
(Talking to Parade, Affleck was two years into his ultimately 10-year marriage to Jennifer Garner, his self-deprecating ways present and accounted for after his debacle of a first engagement to Jennifer Lopez.)
Neither friend finished university but luck was on their side.
"Matt and I had identical interests, so whether we ended up successful or making hot dogs at Dodgers games, we knew we'd end up doing the same sort of thing," Affleck told Interview of the time they spent in different states before rooming together in L.A. "The remaining friends part was pretty consistent. We saw each other all the time, we talked on the phone all the time."
And soon enough, they were hanging out on set.
Their first movie together, 1992's School Ties, featured Damon's breakout performance as a villainous 1950s-era prep school snob, after which his turn as a soldier in the adventure epic Geronimo paid their rent for awhile. (Their first movie with speaking parts, that is—Damon and Affleck were both uncredited extras in the 1989 classic Field of Dreams.)
Affleck started paddling his way to fame playing bully O'Bannion in the teen classic Dazed and Confused. And while juggling auditions and gigs, they leaned into their Cambridge background and cranked out Good Will Hunting, which Damon had started working on at Harvard while taking playwriting and theater direction classes.
After Damon had been in L.A. for about a year, he told Interview, "Ben and I started talking one night, and the script began flowing right out. Then we wrote it very fast," sometimes together and sometimes separately, faxing each other new pages when they were apart. They sold it to Castle Rock in 1994.
"And actually, it was a source of embarrassment for us when we sold the script," Damon continued, "because a lot of our friends really are writers and can write a lot better than we can, except maybe dialogue. Writing a script is different, though, because to me it's not really writing. It's acting, is what it is. We still don't call ourselves writers. We just kind of go, 'Well, I guess that worked.'"
Affleck explained, "If no one else was going to give us the chance to do the kind of acting we could do, we decided we'd just make this movie ourselves—however we could do it, low-budget, whatever. The whole idea was to have a videotape on the shelf at the end of the day and be able to say, 'We made this.'"
Damon recalled of the bidding war that instantly ensued after they showed the script to their agent, "It was the first time we realized how Hollywood works. We'd both gone in for a lot of auditions, but when you actually have something that people are trying to buy from you, it's a whole different thing."
And selling Good Will Hunting was only the beginning.
"The idea was to do what was best for the movie, which was to get it made," Affleck said. "But after a year, we had a falling-out with [Castle Rock] and they gave the script back to us with a 30-day turnaround period, which meant if we didn't sell it within 30 days they'd get the movie back and would be able to do what they wanted with it. It was either make it with who they were asking us to make it with or take this risk. We were basically being fired and offered tickets to the premiere of this thing we'd put three years of our lives into."
After that, their producer Chris Moore brought Miramax to the project, they got word that Gus Van Sant wanted to direct, so long as they were in the movie, and then all the pieces started falling into place.
And not just the pieces of their project.
By the time Good Will Hunting came out in December 1997 and was greeted with nine Oscar nominations, Affleck was known for his fearless turns as major d-bags in Mallrats and Dazed and Confused and notched his first leading-man role in Chasing Amy, while Damon had lost 40 pounds to play a heroin addict soldier in the Gulf War drama Courage Under Fire and starred in the Francis Ford Coppola-directed legal thriller The Rainmaker.
"You wake up one morning and the world is entirely the same," Damon told The Guardian, "and you know, actually, all the things that mattered yesterday are the same today, except the world is forever going to be a totally different place for you."
He added, "That's the mind-f--k and it takes a few years to even get your head around what's happening… I remember my brother said, 'How are you doing?' And I was, like, 'I'm the f--king same, but everyone else is different.'"
Affleck had also told Interview during the relative calm before the storm, "I think our parents were concerned because everybody knows that acting is a difficult career. I don't think they were that happy with the prospect of their kids facing a lifetime of rejection and scraping by for a sandwich and hoping we'd get free refills at the age of 45. But Matt and I were very straightforward about wanting to be actors. I really think that everybody would like to be an actor. Why wouldn't they? It's great work if you can get it. The one thing that prevents most people from saying, 'I'm just gonna go to Hollywood!' is that it seems unrealistic."
Of course, by now they're more than just a couple of actors, or even just movie stars. Rather, they're cultural touchstones, frequently mentioned together but also each representing a different sort of Hollywood archetype. (And forget free refills, they're the heart and soul of Dunkin' Donuts' advertising strategy.)
Since they burst onto the scene, Damon has had the steadier through line—anchoring an action franchise, racking up three Oscar nominations for acting and winning a Golden Globe for The Martian, all with fewer scandals to his bold-faced name than most people in Hollywood, let alone Affleck. He's been married to Luciana Barroso since 2005 and they're raising four daughters together. (Affleck didn't witness Damon's New York courthouse nuptials, but he was there for the Saint Lucia vow renewal in 2013. Damon wasn't at Garner and Affleck's super-private 2005 ceremony, either.)
Affleck's lower points, career and otherwise, are well-documented, but his highs—directing accolades, a Best Picture Oscar win for Argo, playing Batman, fathering three children—have put him squarely on the mountaintop.
"There's nobody who's more misunderstood," Damon said of Affleck, talking to The Hollywood Reporter in 2015 in the weeks following the news that Affleck and Garner were separating after 10 years of marriage. "Ten years ago, the public image of him could not have been farther apart from who he actually is. It was like he was being cast in a role, that he was a talentless kind of meathead, with his whole relationship with Jennifer Lopez."
"He just got cast as this person that he wasn't," Damon shared. "It was just really painful. It was painful to be his friend, because it wasn't fair, you know? To my mind, nobody really got him at all. And through his work, he climbed from the bottom of the mountain all the way back up to the top and past where either of us had ever been."
And Affleck has never taken Damon's enduring support for granted.
"I can't tell you how valuable it is to have somebody who's been through things with you, ups and downs, who knows what your life experience is like, who can identify with that," he told Entertainment Tonight, referring to Damon, in 2017. "It's an incredibly valuable friendship and it's very precious and so is my friendship with my brother. I don't know what I would do without those guys."
But as longtime dear friends, Affleck and Damon have really seen and heard it all when it comes to their enviable bond and professional partnership, including jokes that Affleck was a millstone around Damon's creative neck when they wrote Good Will Hunting, errant reports of a feud and—before the age of social media so not as widely spread, but there all the same—speculation that they were actually a couple.
"When Ben and I first came on the scene, there were rumors that we were gay because it was two guys who wrote a script together," Damon recalled to The Guardian in 2015. "I know. It's just like any piece of gossip...and it put us in a weird position of having to answer, you know what I mean? Which was then really deeply offensive. I don't want to, like, [imply] it's some sort of disease—then it's like I'm throwing my friends [who are gay] under the bus."
A couple years later, Affleck and Damon did have to confront a painful aspect of their early success—the fact that disgraced producer Harvey Weinstein was the financial force behind not only the Kevin Smith movies that gave their careers a boost but also Good Will Hunting.
In the aftermath of the slew of sexual assault and harassment allegations laid out against Weinstein starting in October 2017 (he's since been convicted of rape in New York and Los Angeles and sentenced to 23 and 16 years in prison, respectively), Affleck and Damon tried to make it clear that they wanted to be part of the solution as Hollywood moved forward as a more equitable, inclusive, safe place to work.
"We know this stuff goes on in the world. I did five or six movies with Harvey. I never saw this," Damon told Deadline. "I think a lot of actors have come out and said, 'Everybody's saying we all knew.' That's not true. This type of predation happens behind closed doors, and out of public view. If there was ever an event that I was at and Harvey was doing this kind of thing and I didn't see it, then I am so deeply sorry, because I would have stopped it."
Affleck said he'd be donating residuals from his Miramax films to RAINN (Rape, Abuse & Incest National Network) and Film Independent. Ultimately, Affleck added, "I thought I had a sense of the scope of the problem and I thought I understood it, and the truth is I really didn't."
Then, in December 2017, Damon's dad, Kent, died after a long bout with cancer, and while the actor was devastated, his father's death hit Affleck really hard too.
"The guy is like a brother to me and there are ups and downs in life," Damon shared with People in March 2018. "It was a bad year for him, too. He was very, very close to my father, they had a great relationship. Loved each other a lot. So last year was no real picnic for him either."
That summer, Affleck returned to rehab for 40 days, after which he continued with outpatient treatment and the never-ending efforts that go into the process of staying sober, his support system from years past by his side—or just a phone call away.
But while their mutual admiration had remained intact, it had been awhile since Affleck and Damon last cranked out the kind of script they wanted to make. In any case, in 2019 they got busy adapting Eric Janger's tale of real-life medieval revenge The Last Duel, with the help of writer-filmmaker Nicole Holofcener.
The pandemic-delayed production, directed by Ridley Scott and starring Damon, Adam Driver and Jodie Comer, with Affleck in a scene-chewing supporting role, fizzled upon arrival in 2021—but it was well-reviewed and the film's screenwriters realized that, if they wanted to hang out more, they should probably just keep working together.
"The experience was so fun and rewarding," Affleck said during a joint interview with Damon, "and I realized, having collaborated with other people in the interim period...Wow, we really have a great collaboration. I love working with this guy and I love hanging out with him. And when you get older and you have kids and you have a life...There's got to be a reason you're going to leave the house and go do something."
They even managed to shoot Air ahead of Affleck and Lopez's 19-years-in-the-making July 2022 vow swap in Las Vegas, followed by their Georgia wedding a month later, which Damon and his wife attended.
"How else would I be?" Damon quipped on The Jess Cagle Show when quizzed about the awe-inspiring resurgence of Bennifer in 2021. "Like, would I be unhappy? Like, 'I hate true love.'"
He added, deadpan, "I wish them nothing but, you know, hardship."
It's all good vibes now, though, with Air getting great reviews and America running on Affleck and Damon's 40 years of friendship.
Asked about their renewed commitment to collaborate whenever possible, Damon explained to Bill Simmons, "If we don't start getting proactive about working together, we're not going to work together. And what an insane opportunity to even have, to be able to work together at this stage of our lives and careers is f--king amazing. Why not avail ourselves of that?"
Added Affleck, "The only thing I could imagine to be better is working with your kids, and I'm pretty sure my kids have ruled that out."
(Originally published Aug. 8, 2020, at 9:15 a.m. PT)