The many failures of Ben Affleck He's learnt to live with disappointment

Handsome in a brash and bro-ish way, with an oblong head and beefy, six-foot-four physique, Affleck started out playing jerks in School Ties, Richard Linklater’s Dazed and Confused and Kevin Smith’s Mallrats. He graduated to doofus in Chasing Amy but even his nicer characters weren’t very smart. So when he and Damon broke through in 1997 with their Oscar-winning screenplay for Good Will Hunting, the impression was that, off screen as well as on, Damon was the star and Affleck the sidekick. I still remember a waspish line from Esquire’s film critic, to the effect that Ben Affleck was put on the earth for the sole purpose of making Matt Damon look like the clever one.

Their next moves compounded that stereotype of art vs commerce. Damon moved into prestige pictures such as Saving Private Ryan and The Talented Mr Ripley, before striking oil with the Bourne franchise. Affleck became an action star in Armageddon, Pearl Harbor, Daredevil and The Sum of All Fears, none of which played to his strengths. In a recent interview with Damon, Affleck joked about feeling “deeply jealous and developing a sense of inadequacy and self-loathing” but it wasn’t entirely a joke: he wasn’t getting the same opportunities. “It’s not as if actors are turning down something way better,” he once told me. “It really doesn’t come down to X vs Y so much as X vs nothing.”

In smaller movies, he was once again a braggart (Shakespeare in Love) or an asshole (Boiler Room), which might explain why his brief experiment with romcoms never paid off. Only Roger Michell’s 2002 drama Changing Lanes, in which he clashed with Samuel L Jackson, was a persuasive advertisement for his acting chops. Meanwhile Gwyneth Paltrow, his girlfriend from 1997 to 2000, publicly described him as a “complete knucklehead”, which didn’t help. “What many people don’t know is that he’s crazy smart, but since he doesn’t want that to get awkward, he downplays it,” said David Fincher years later.

Affleck never seemed at ease in blockbusters. If I were ranking his performances, I would put his brilliant comic turn in the DVD commentary for Armageddon in the top five. He’s like a college smart-alec heckling the screen, only he’s actually in the movie. Unfortunately, it’s not a great look if you come across as thinking you’re too good for the movies you’re being paid handsomely to star in. He recalls challenging director Michael Bay on an absurd plot point in that thoroughly absurd film: “He told me to shut the fuck up.” The real joke’s on Affleck for thinking he’s above it all.

All in all, Affleck’s reputation was in a precarious state when he met Jennifer Lopez on the set of Gigli in 2001 and everything went awry. Gigli was the kind of brutal, unqualified flop that might as well have police tape around the scene of the crime. Their next movie together, Jersey Girl, also tanked. The hostile reception was inextricably tied up with the stars’ two-year relationship and the rise of celebrity media at its cruel, carnivorous worst. Affleck later blamed snobbery and racism: even his taste in women was deemed trashy. Whatever the reasons, no relationship could have survived the obsessive scrutiny applied to “Bennifer”. Their wedding was first postponed and then cancelled. The backlash left them both shellshocked. When Affleck bumped into Damon around the release of Gigli he said: “I’m in the worst possible place you can be. I can sell magazines, but not movie tickets.”

GQ called Affleck “the world’s most over-exposed actor”. The Los Angeles Times wrote a long autopsy called “Ben Big’s Fall”. Yet Affleck was never a bad guy. Critics often praised his capacity for self-doubt and self-deprecating humour, so it’s apt that he won his first acting awards for playing George Reeves in 2006’s Hollywoodland, the Sixties Superman actor who was sent flying by fame and brought to earth with a humiliating crash. He’s stayed on good terms with his exes (very good in Lopez’s case) and he’s loyal to his friends. Directors including Linklater and John Frankenheimer have called him one of the nicest actors in the business. He’s always been a great interviewee, providing a clear-eyed running commentary on his career.

Now married to his Daredevil co-star Jennifer Garner, Affleck rebounded by moving behind the camera for his directorial debut, 2007’s Gone Baby Gone, starring his brother Casey. “Nobody knew whether he was going to be any good or not, so people were surprised,” Casey told me at the time. “But I wasn’t surprised. I knew that he’s so much smarter and more interesting than the person that’s depicted in the gossip magazines.” Suddenly there were comparisons to Robert Redford, the gold standard for actors turned directors, but Affleck still appeared bruised and wary when I interviewed him. Whenever talk turned to his rough patch, he began nervously flicking a bottle opener. Poker players would call that a giant tell. He still seemed to think that his comeback was fragile.

Affleck directed another satisfying crime thriller, The Town, in 2010 and then Argo in 2012. “We were wrong about Ben Affleck,” wrote the New Yorker’s Anthony Lane. “Few of us, watching Armageddon and Pearl Harbor, could see a way out, or back, for an actor so utterly at the mercy of his own jawline.” But Hollywood’s ambivalence towards him was betrayed by the fact that he was only the fourth person in the history of the Academy Awards to win Best Picture without getting a Best Director nomination, as if Argo’s excellence had nothing to do with its director and star. OK, he wasn’t the ideal choice to play CIA agent Tony Mendez, but who else was going to give him a part like that?

Affleck took a giant step backwards with the snoozy 2016 mob drama Live by Night but he still has a better actor-director track record than George Clooney. He’s shown real flair for action sequences, and a talent for getting great work out of ensemble casts, steering five actors from his first three movies to awards buzz. So it seemed incomprehensible when, in the afterglow of Argo, he signed up to play Batman. Affleck is always torn: while he may have a low opinion of superhero and action movies, he can’t quite let go of stardom. He didn’t seem like he really wanted to be Batman but then he was playing a Bruce Wayne who didn’t want to be Batman anymore either: angry, jaded, bitter. He might have pulled it off with a better director than Zack Snyder. A 2017 alcoholic relapse put paid to a solo Batman movie, which was probably for the best.

Affleck has had bad luck with superheroes. His recent action movies, The Accountant and Triple Frontier, are background noise. He’s also struggled to find sympathetic directors. Unlike his contemporaries, he’s never worked with Scorsese, Tarantino, Wes Anderson, Steven Soderbergh or the Coen brothers. His movie with Terence Malick, To the Wonder, was one of the director’s weakest. The towering exception, and his best performance to date, was David Fincher’s Gone Girl. With a perfect blend of charm and menace, his Nick Dunne is a fuck-up who could be victim, villain or both. Affleck isn’t playing himself but he’s playing with who people think he is. “I think it’s interesting how we manage the best version of ourselves,” he told the New York Times, “despite our flaws and our weaknesses and our sometime tendencies to do the wrong thing.”

Where does Affleck find a lane these days? The failure of Ridley Scott’s The Last Duel, which Affleck co-wrote and appeared in, confirms that the movies he really likes barely exist in cinemas anymore. He was sensitive in The Tender Bar and convincing as a recovering alcoholic in The Way Back but neither move made much impact. At the same time, he’s yet to commit to a prestige TV series in the vein of True Detective or Mare of Easttown. His slate of forthcoming projects looks underwhelming: two more outings as Batman, his eighth Kevin Smith movie, and a sci-fi thriller called Hypnotic. His return to directing with a film about Nike co-starring Damon could go either way. I’d love to see him play a role that fully exploits his talent for exhausted masculinity and gallows humour — Raymond Chandler’s Philip Marlowe, perhaps.

At least he seems happy now. More than any other movie star, Affleck is relatably candid about life not working out as planned. He has a consciousness of disappointment and failure that you don’t find anywhere else. Cruise and DiCaprio are too successful, McConaughey too upbeat, Johnny Depp too weird. It makes me want to root for him, which is why I find his recent marriage to Lopez, 20 years after their last attempt, so cheering. We’d all like to believe that life gives us second chances.

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