There are moments on Matt Damon and Ben Affleck’s press tour that drift off-script — teasing each other, barely finishing a sentence, laughing mid-thought. It starts to feel less like promotion and more like you’re invited into an inside joke that’s been running for 45 years. I’ve watched these Boston boys cross paths for decades, and somehow this version feels like the most relaxed and fun one yet.
The reason they’re back in this rhythm is The Rip, their new Netflix film, which has put the longtime friends on the road together — something audiences don’t actually get from Damon and Affleck all that often anymore. Their shared history runs deep: childhood friends from Cambridge, Mass.; Oscar winners for Good Will Hunting; collaborators on films like Air and The Last Duel. Through their personal detours — like Affleck’s two divorces — they’ve shown up for each other during very public chapters. They’ve grown up, split paths and found their way back to each other more times than most Hollywood friendships survive.
That familiarity has surfaced over the last week in ways you can’t really script. Here are five of my favorite moments from this promo run.
The one where they roast each other
Things really clicked when the actors took their friendship tour to the Today show, where the conversation quickly drifted from The Rip into a greatest-hits reel of their shared history. The two casually revealed that when they were starting out, they once shared a bank account while schlepping back and forth to auditions in New York. “There was not a lot of money in the bank account,” Damon said.
From there, the dynamic did what it always does. Affleck roasted Damon for getting ripped for The Odyssey, sending both of them into a laughing fit.
Asked to name Damon’s best trait, Affleck pivoted from comedy to sincerity without warning. “The truth is he’s a really deeply, fundamentally good man,” he said. Damon, caught off guard, deadpanned, “I’ve got nothing.” (He ultimately returned the compliment.)
Then came the domestic-style digs. Affleck didn’t hesitate when asked about Damon’s least favorite trait: “Not great at cleaning up around the house” — prompting Damon to jump in with a quick defense: “Hey, when I was younger!”
And just when it seemed like they’d exhausted the archive, Damon dropped perhaps the most shocking reveal of all when it was his turn: Affleck had arrived early. “We got here this morning and Ben was three minutes early,” Damon said, before adding the kind of kicker only a lifelong friend could deliver. “That’s the first time in 45 years he has not been late.”
The one where Damon gets (lovingly) humbled at home base
If you’re looking for proof that even Damon doesn’t get a free pass at home, this was it. The Oscar winner made a red carpet appearance at the film’s New York City premiere with his wife, Luciana, and three of their four daughters — Isabella, 19, Gia, 17, and Stella, 15 — and the result was one of the most unexpectedly charming moments of the night.
Matt Damon poses with his wife, Luciana Barroso (in red), and daughters (from left) Isabella, Gia, and Stella. (John Nacion/FilmMagic)
(John Nacion via Getty Images)
Damon isn’t known for turning premieres into family affairs, which is precisely why this one landed. If he hadn’t brought his girls along, we never would have gotten the moment where they gently called him out for an awkward pose — poking fun at his go-to stance, laughing in real time and reminding everyone watching that no matter how many movies you’ve made, to your kids, you’re still just dad.
The exchange felt unscripted, warm and completely unfiltered — the kind of rare red carpet moment that sticks.
The one where they remind us they’re just Boston boys
Affleck and Damon stopped by The Tonight Show Starring Jimmy Fallon, and one segment immediately became the standout: “Three Guys From Boston Say Every Town and City in Massachusetts.”
Dressed head to toe in Boston gear, Affleck, Damon and Fallon listed every town and city across the state — alphabetically, from Abington all the way to Yarmouth — in thick Boston accents, for more than four minutes.
The one where Damon learns he wasn’t the crush
Things took a hilariously personal turn on The Howard Stern Show when Damon revealed that his wife originally thought Affleck was the more attractive half of the BFF duo. According to Damon, the confession came months into their relationship — and it came straight from Luciana’s best friend.
“After we’d been together for probably a few months … I met her best friend from high school,” Damon explained. The two women had gone to see Good Will Hunting together back in the day — and while the friend thought Damon was “the cute one,” Luciana apparently disagreed. “She thought Ben was the cute one,” Damon said, admitting that his wife later owned up to it. “I’m like, ‘You got the wrong one?’ She told me that 23 years ago.”
Affleck was quick to jump in.
“She’s a great producer and a really good friend, and yeah, I never got that vibe from her,” he said, drawing laughs from Damon and Howard Stern. “So I think something I did in real life rubbed it off.” Damon, never missing a chance to land the button, added: “Finally, she met him and all that went away.”
The one where they change the rules for everyone else
One of the most quietly meaningful moments of The Rip press run had nothing to do with jokes — and everything to do with who actually benefits when a movie succeeds. For the Netflix film, Affleck and Damon pushed the streamer to agree to a rare deal that would reward the crew with bonuses if the movie performs well — a structure that’s almost unheard of in the streaming era.
Affleck explained the thinking in an interview with the New York Times, framing it as both practical and philosophical. “We wanted to institute fairness and address some of the real issues that are present and urgent for our business,” he said.
Under the agreement, all 1,200 people who worked on the nearly $100 million production — a crime thriller about two Miami cops who stumble upon hidden money — are eligible for a one-time bonus if The Rip meets performance benchmarks on Netflix. The film will be evaluated over its first 90 days on the platform and measured against comparable titles, with the possibility of additional payouts if it overperforms. It’s not flashy, and it’s not viral — but it may end up being one of the most consequential moments of the entire tour.