Boston Bond: The Truth About Matt Damon and Ben Affleck's Winning Friendship

After they won Oscars in 1998 for writing Good Will Hunting, here's why the world invested in the bond between Matt Damon and Ben Affleck.

By Natalie Finn Oct 08, 2020 4:15 PMTags
Ben Affleck, Matt DamonMichael Kovac/Getty Images

"Ben Affleck and Matt Damon are childhood friends. They appeared together in Chasing Amy and Good Will Hunting, for which Damon received a Best Actor nomination. This is their first Academy Award."

So intoned the announcer as Affleck and Damon, so boyish-looking at 25 and 27 in their plain tuxedos that they may as well have been 14, headed to the stage in 1998 to accept their Oscars for Best Original Screenplay, the film they decided to write together to give themselves the sort of material that interested them having worked out to the tune of nine Academy Award nominations, including Best Picture.

Like a proud dad, co-star Robin Williams—a winner that night for Best Supporting Actor and, Affleck later said, a major factor in the movie getting made in the first place—gave them hearty hugs.

"We're just really two young guys who were fortunate enough to be involved with a lot of great people…. There's no way we're doing this in less than 20 seconds," Affleck gushed excitedly as they dissolved into their thank-yous, with extra-special shout-outs going to their mothers ("Matt's mom, the most beautiful woman here," Affleck agreed), Damon's dad and the city of Boston—the setting for both Good Will Hunting and the formative years of Matt and Ben's extra-special friendship.

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Matt Damon: Movie Star

First, let's clear up a few things: Damon was barely in Chasing Amy (which legitimately starred Affleck) and the 1992 drama School Ties was actually their first movie together (and Damon had the much bigger role). And yes, we know, the majority of the Harvard-set Good Will Hunting action took place in Cambridge, Mass., which, though considered part of the greater Boston metropolitan area, is a different city.

But none of those persnickety details changes the fact that the absolute best thing about Affleck and Damon's friendship—which began when they were 8 and 10, respectively, and living a couple streets away from each other in Cambridge—is that it's always been the real deal, not some Hollywood construct to make for a better Good Will Hunting origin story.

And four decades later, with Damon celebrating his 50th birthday on Oct. 8, they remain the best of friends. Damon may have ended up sequestered in Ireland with his wife and daughters during the beginning of the pandemic in March, but before everything shut down he and Affleck had enjoyed their annual winter ski trip to Montana with their families. 

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Ben Affleck: Movie Star

"I think we're pretty similar," Affleck told ABC News in 2017, asked how he and Damon had changed since the 1980s. "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.

"Last night he just emailed me and was like, 'Come over and watch Monday Night Football,' 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."

And it all started in Cambridge, where Ben (who was born in Berkeley, Calif.) moved with mom Chris and dad Tim (who divorced when Ben was 11 and brother Casey Affleck was 8), and Damon, a native son, lived with parents Kent and Nancy and his 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."

Added Affleck, "I remember exactly what he was like: gregarious, outgoing. 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 for a long time had no one to talk about it outside of his family (Casey also having been bit by the performance bug early on). But his neighborhood buddy and classmate at Cambridge Rindge and Latin High School showed 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. 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." 

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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." (Having dusted himself off after his debacle of an engagement to Jennifer Lopez and two years into his marriage to Jennifer Garner at the time, his tendency toward self-deprecation was present and accounted for.)

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Neither finished college—Affleck moved to Los Angeles after a few months in Vermont; Damon, who had a head start on higher education over his younger friend, lasted three years at Harvard before the siren song of L.A. beckoned—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 California. "The remaining friends part was pretty consistent. We saw each other all the time, we talked on the phone all the time."

While juggling auditions and gigs (Damon's big break came playing a villainous 1950s-era prep school snob in School Ties, after which Geronimo paid their rent for awhile; Affleck starred in a short-lived TV drama called Against the Grain and illustrated that using steroids was bad in an episode of HBO's Lifestories: Families in Crisis), they leaned into their experiences growing up in the Boston area 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.'"

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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.'"

Of the bidding war that instantly ensued after they showed the script to their agent, Damon recalled, "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."

But considering the movie didn't come out for more than three years, obviously complications arose.

"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, and which was now starring—"

"Someone who wasn't us," Damon said. 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.

Miramax Films

"I laughed the entire time we wrote," Damon told The Guardian in 2015. "It was a really joyful experience." When the movie became a sleeper hit and the Oscar buzz began, he recalled, "You wake up one morning and the world is entirely the same 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.'"

Evan Agostini/Getty Images

By the time Good Will Hunting came out, in December 1997, Affleck was known for his fearless turns as major d-bags in Mallrats and Dazed and Confused and had proved he could carry a romantic comedy with Chasing Amy, while Damon had a gritty supporting role (he lost 40 pounds to play a heroin addict soldier) in the Gulf War drama Courage Under Fire and had starred in the legal thriller The Rainmaker.

"Making movies has become such a golden ring, and it's all such a big business, that the rewards system has gotten totally out of whack," Affleck lamented to Interview ahead of Good Will Hunting's release. "Suddenly, you're treated in a manner befitting someone who is actually an important person. You get the best table, you get all this money, you get people saying, 'No, no, I'll pay the check.' It implies there's a way of treating certain people as if they're better than other people, and I don't think you should do that.

"It's difficult for me to see the benefits of fame," he continued, "except that you get the chance to do the stuff you want to do. Aside from that, the only other good thing I can imagine from being famous is that when I introduce myself, I no longer have to go, 'A-f-f…' 'A-s-s…?' 'No, A-f-f, like Frank.'"

Within months he'd be in Shakespeare in Love and dating its star, Gwyneth Paltrow, and then top-lining the 1998 summer blockbuster Armageddon, which made half a billion dollars. So, yes, the spelling of his name finally started to proceed him.

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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."

As he reflected to Parade earlier this year, "We both were nerdy kids who wanted to be actors. It's sort of amazing that it actually came true, considering how, like, totally naïve and foolish we were."

Jeff Kravitz/FilmMagic, Inc

Of course, by now they're more than just a couple of actors, or even just movie stars. Rather, they're a pair of cultural touchstones, frequently mentioned together but also each representing a different sort of Hollywood archetype.

Damon has had the steadier career, excelling in all genres, 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 some. He's been married to Luciana Barroso since 2005 and they're raising four daughters together.

Affleck, meanwhile, is a tabloid favorite whose career has been all over the place. But his highs—a Best Picture Oscar win for Argo and directing honors from everyone except the Academy (which was widely ridiculed for overlooking him); playing Batman; becoming a father of three children—are certainly the kind you write home about.

At least he's never had to go far to talk to his childhood best friend about all of it, be it his personal life or all that showbiz B.S. that Damon is also quite familiar with.

Eric Charbonneau/Invision for Warner Bros./AP Images

"These guys are both super interested in doing a range of things—Matt's diversity as an actor and Ben going down the road of writing, acting and directing," their agent Patrick Whitesell told The Hollywood Reporter in 2015. "They're all things that come from an artistic place, and they love the challenge of it. That spark is where they are very similar. And on a philanthropic level, they're both very, very committed."

So, they're more than just pretty faces who've logged time as People's Sexiest Man Alive, Affleck in 2002 and Damon in 2007.

They've launched two production companies together over the years, the since-shuttered LivePlanet (the shingle behind Project Greenlight back in the mid-'00s) and their current Pearl Street Films (named after the route they took to get to each other's houses as kids), which is housed at Warner Bros.

And having expressed suspicion of actors who talk the talk without walking the walk earlier in their career, they each have humanitarian causes they actively champion, Damon cofounding Water.org to support clean water projects around the world, while Affleck helped establish the Eastern Congo Initiative in 2010 (after visiting the region five times because he wanted to know what he was talking about).

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"I was just talking to Matt about this last night," Affleck, now 48, told Parade, "that as we've gotten older, we kind of have our own definitions of success or failure that we trust more than feeling the need to look to other people for approval or encouragement.

"I've just learned to really trust my own sense of, 'Did I grow from this? Did I get something valuable from this?'"

He was promoting his most recent film, The Way Back, in which he plays a high school basketball coach with a drinking problem who's trying to recover his self-respect and not let any more people down—a not entirely foreign concept to Affleck, who's been very candid about having addiction issues and has spent stretches in treatment multiple times over the past 20 years. 

Angela Weiss/Getty Images

"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 Ben and Jennifer Garner were divorcing 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. 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."

For his part, 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."

Any contention these days has more to do with who's better friends with Tom Brady, for years the quarterback of their beloved New England Patriots, or how successful Jimmy Kimmel has been at stealing Affleck away from his avowed nemesis Damon (all three sat at a Dodgers-Red Sox World Series game together in 2018).

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But over the years Affleck and Damon have really seen and heard it all (about themselves and others), 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—a rumor 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 informed 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 of 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 their Oscar-winning triumph itself, Good Will Hunting. Weinstein was the first person Affleck thanked onstage during their otherwise-worth-remembering speech.

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After their own stumbles (well-meaning but insensitive remarks from Damon, as well as suspicion that he had helped kill a story years ago; embarrassing old video of Affleck seemingly groping Hilarie Burton on TRL in 2003) in the aftermath of the slew of sexual assault and harassment allegations laid out against Weinstein, followed by dozens of other prominent men, starting in October 2017, Affleck and Damon tried to make it clear that they wanted to be part of the solution as Hollywood moves 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 on The Late Show With Stephen Colbert that hearing about Weinstein's "terrible crimes" did affect how he felt about the movies they'd made together. "It sort of tainted that a little bit to realize while we were having these experiences and making these movies, there were people who were suffering and dealing with awful experiences," the actor said. "I didn't really know what to do with that, you know? It's hard to know." 

He 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, that December, Damon's dad, Kent, died after a long bout with cancer, and while Damon 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 at a Water.org event in New York. "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—Garner, his kids, his parents, brother Casey and best friend Matt—intact from years past.

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Next up for Affleck is the summer 2021 release of the thriller Deep Water, in which he co-stars with his now real-life girlfriend Ana de Armas, the couple revealing themselves to be more than quarantine buddies this past spring. ("We're playing husband and wife, and it's sort of a thriller drama, but the actress, who's amazing—Ana de Armas—is very, very funny, and she makes me laugh every day at work," he nonchalantly told Parade before the pair had gone public.)

Kind of coincidentally, Damon, last seen in Ford vs. Ferrari, shot a movie called Stillwater that's due out sometime next year, in which he plays an Oklahoma dad who has to hightail it to France after his daughter (Abigail Breslin) is arrested for murder.

And in addition to continuing to develop projects through Pearl Street Productions (in 2018 they announced they'd be adopting an inclusion rider for all future productions), last year Damon and Affleck teamed up again to write for the first time since Good Will Hunting, joining forces with Nicole Holofcener (Lovely & AmazingCan You Ever Forgive Me? ), to adapt Eric Janger's medieval revenge novel The Last Duel. With director Ridley Scott behind the camera, they started filming in France in February and Damon was still shooting in Ireland in March when production was suspended due to the pandemic. They were finally able to resume last month and, as of now, the film—starring Damon, Adam Driver and Jodi Comer, with Affleck in a supporting role—is due out Oct. 15, 2021.

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"We're constantly accused by people who come in and out of our circle of friends that we're the most boring people ever," Damon told Interview 23 years ago. "There are people who go, 'I got tickets to see so-and-so, and why don't you guys come?' We're like, 'Yeah, whatever,' and end up at the same bar every night with the same people telling the same old jokes. We've always been that way."

Indeed, they've always had each other.

Hometown Kids

Damon and Affleck share a scene as troubled genius Will and his devoted childhood pal Chuckie in their breakout hit Good Will Hunting, which was nominated for nine Oscars, including Best Picture, Best Actor for Damon, Best Supporting Actor for Robin Williams and Best Original Screenplay.

Made It

Awards season heats up in 1998 as Ben and Matt walk the carpet at the Golden Globes, celebrating Good Will Hunting's four nominations.

Hey, We Won!

Affleck and Damon pose with their first Golden Globes, Best Screenplay for Good Will Hunting. Affleck won another, in 2013, for directing Argo, and Damon won in 2016, Best Performance by an Actor in a Motion Picture, Musical or Comedy, for The Martian.

Thank You, Boston!

Best Original Screenplay winners Affleck and Damon make sure to give a shout-out to their formative hometown, which helped inspire the first-ever movie they wrote together, Good Will Hunting.

Golden Men

Damon and Affleck relish their Oscar win in 1998.

Prettiest Gals in the Room

Affleck and Damon show off their Oscar night dates—moms Chris Affleck and Nancy Carlsson-Paige—in 1998.

For Laughs

Damon and Affleck teamed up as fallen angels Loki and Bartleby in Kevin Smith's 1999 comedy Dogma.

Just a Couple of Dudes

Matt and Ben dress down in Miami Beach in 2006.

Super Men

Damon supports his buddy in 2006 at a screening of Hollywoodland, in which Affleck played George Reeves, the tragic actor who played Superman in the 1950s-era TV series.

Date Night

Both pals got married in 2005, and in 2008 they enjoyed a night out all together in Miami Beach. Affleck and Jennifer Garner, who have three children together, split up in 2015 and eventually divorced in 2018. Damon and wife Luciana, parents of four daughters, will celebrate 15 years of marriage in December 2020.

Same Old, Same Old

Matt and Ben hang out, 'cause that's what they do.

You Earned It, Buddy

Naturally, Affleck was among the stars who feted (and roasted) Damon while presenting him with the American Cinematheque Award in 2010.

"I kind of started out at the same time as the guy, so this is a special night for me, too," Ben quipped.

Best Buds

They always look ready for a marathon poker tournament.

Creative Control

The chums celebrate the return after 10 years of Project Greenlight, their HBO series about bringing indie films to fruition, in 2014.

Family Matter

Affleck is on hand to support brother Casey Affleck and honorary brother Damon at the 2014 premiere of Manchester by the Sea, which Affleck and Damon co-produced and for which Casey would go on to win the Oscar for Best Actor (and forget to thank Ben, which turned into a whole funny thing).

The Good Shepherds

Affleck and Damon are on hand to support Project Greenlight's season four winner, The Leisure Class, at the film's 2015 premiere.

Good Will Reading

Affleck and Damon reprised their roles as Chuckie and Will for a live reading of Good Will Hunting in 2016, and enlisted some of their talented friends to sit in, including John Krasinski, who narrated; Emily Blunt playing Skylar; Keegan-Michael Key as Billy; and Margo Martindale filling the mighty shoes of the late Robin Williams as Dr. Maguire.

Wingman

Damon celebrates Affleck landing the Caped Crusader cowl in Batman v. Superman: Dawn of Justice and ensuing DC Universe films, 20 years after both actors auditioned for and didn't get the role of Robin back when Tim Burton was making Batman movies. (The sidekick eventually showed up in Joel Schumacher's Batman Forever.)

We're Back!

Affleck and Damon reunite at the Oscars in 2017 to present the Academy Award for Best Original Screenplay, 19 years after their momentous win.

Wait, What?

And here they are looking as amazed as anybody to see that Moonlight was the actual Best Picture winner instead of La La Land.

Sporting Scene

Matt and Ben enjoy a night out with fellow Boston sports nut Bill Simmons.

What Curse?

The lifelong Red Sox fans got emotional celebrating their team's 2018 World Series title.