Let’s examine the shifting fortunes of the Matt-and-Ben brothership
The yin-yang journey of Hollywood’s two best bros.
Late ’90s: Just Two Guys Having a Good Time With their moms. Photo: Kevin Mazur/WireImage With Good Will Hunting, Damon and Affleck burst onto the scene as best bros who do everything together — make movies, love their moms, win Oscars. They’re both instantly catapulted onto the A-list, but their paths as leading men begin to diverge. Affleck sets his sights on bigger productions like Armageddon (1998); Damon prefers director-driven dramas like The Talented Mr. Ripley (1999) or, um, The Legend of Bagger Vance (2000). Ben also gets his first high-profile relationship, with Gwyneth Paltrow, while Matt ends his romance with co-star Minnie Driver in public fashion, breaking up with her on Oprah.*
Early 2000s: Early Peaks The Bennifer years. Photo: Kevin Winter/Getty Images In a trend that will persist throughout his career, Affleck blockbusters like Pearl Harbor (2001) and Daredevil (2003) earn lots of money but negative reviews; he himself often seems ashamed to be in them. But they pale in comparison to the tabloid colossus that is Bennifer 1.0, which leaves him temporarily a laughingstock with two notorious bombs on his résumé (2003’s Gigli and 2004’s Jersey Girl). While his friend’s in his flop era, Damon’s at his peak, landing a pair of thinky franchises, Ocean’s Eleven (2001) and The Bourne Identity (2002), that sustain him for the next decade. (He also starts dating Luciana Barroso, the regular-degular woman he’s still with today.)
Mid-to-late 2000s: Recharge Bourne again. Photo: Universal Pictures Damon’s hot streak continues: more Ocean’s (2004 and 2007) and Bourne (also 2004 and 2007) movies, and in between, an addition to the Boston Movie Canon with The Departed (2006). A chastened Affleck goes into character-actor mode, earning a Golden Globe nom for Hollywoodland (2006). He marries Jennifer Garner and reinvents himself as a filmmaker with his own Boston Movie, Gone Baby Gone (2007). Tellingly, he does not star. headtopics.com
Early 2010s: Affleck’s First Comeback Remember those Oscar nominations and wins? Photo: Warner Bros. Affleck’s back, baby! He directs himself to a hit in The Town (2010, another Boston Movie), and follows it up with another hit that wins Best Picture in Argo (2012). Taking a page from Damon’s book, he gives himself over to David Fincher on Gone Girl (2014), producing arguably his best performance. Damon is playing with house money at this point, and while star vehicles like We Bought a Zoo (2011) and Elysium (2013) are a step down in quality, he has fun with supporting turns in True Grit (2010), 30 Rock (2010-2011), and Behind the Candelabra (2013), and earns the world’s most forgotten Oscar nom for Invictus (2009).
Mid-to-late 2010s: Middle-Age Malaise *Looks longingly out onto the ocean.* Photo: Warner Bros. Not a bright spot on either star’s CV. Affleck takes the role of Batman in Zack Snyder’s DCEU (2016-2017), which becomes a poisoned chalice — his press-junket misery goes viral — and his next film as a director, Live by Night (2016), flops. At the same time, his personal life is in turmoil. He and Garner divorce, he undergoes two stints in rehab for alcohol abuse, and he gets an infamous back tattoo of a phoenix. Damon has a mini-comeback with The Martian (2015), but, after nearly 20 years of low-key stardom, his diversity comments on Project Greenlight add a frisson of out-of-touch white guy to his star image. (His role in 2016’s The Great Wall does not help.) The coming of the Me Too era in 2017 is an awkward fit for the two Weinstein Company stablemates. Affleck apologizes after video of him groping TRL host Hilarie Burton in 2003 resurfaces, while Damon finds his opinions on sexual misconduct are incredibly unasked-for.
Early 2020s: Back to Their Roots Grab your Dunkies. Photo: BG004/Bauer-Griffin/GC Images The Way Back, Affleck’s attempt at a Serious Actor comeback, is derailed by the coronavirus pandemic. But his second life as a human meme goes into overdrive — dating Ana de Armas, chugging Dunkin’ Donuts, and, after breaking up with de Armas, reconnecting with Jennifer Lopez. Except that this time, everyone loves them! Damon’s quarantine is quieter: He’s locked down in an Irish seaside town, where he becomes a beloved fixture. He earned good reviews for Stillwater (2021), before, well, you know. Now comes The Last Duel, where he once again takes center stage, with Affleck in a supporting role. Will Ben’s new mojo rub off on him?
*This post originally misstated the nature of Damon’s relationship with Minnie Driver. Read more: New York Magazine »
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