He’s a leading man, he’s a reluctant superhero, he’s a tabloid fixture, he’s known for trying to carry too many Dunkin’ Donuts beverages in one trip. Ben Affleck is a legit American treasure, a square-jawed, cleft-chinned heartthrob who can really act (and write, and direct, and smoke dejectedly). Affleck’s done it all in his thirty-year career: taking home a Best Screenplay Oscar in his mid-twenties, going on to direct a Best Picture winner, patting J-Lo’s butt in the “Jenny On The Block” video and re-patting for the paparazzi twenty years later. He’s grown up before our eyes, from goateed ‘90s indie-movie boy to the co-founder of Nike in his latest film, AIR, and we believe he’s worthy of celebration. So we here at Esquire have taken it upon ourselves to rank his best movies. Here they are, plus a few quick roundups of the movies that got no love from our voters and can therefore no longer be considered Affleck Canon.
37. Gigli (2003)
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I don’t know how Gigli ended up at the bottom. Everyone involved in this list, except for me, has failed you, the reader. Affleck stars as Larry Gigli, a Los Angeles mobster who is tasked with kidnapping someone’s mentally challenged younger brother. Whose younger brother? It doesn’t matter. Let the plot take you. Anyway, Gigli’s boss doesn’t have faith in him, so he sends a backup in the form of Ricki, a lesbian played by Jennifer Lopez. But also, Ricki isn’t a lesbian. She’s the lover of Ben Affleck in real life, which means she must be the lover of Ben Affleck’s character. I’ll be frank with you. I don’t remember how the film ends. I just remember how it made me feel, and that was as high as a kite. Like, imagine being in a K hole while listening to “Love Don’t Cost a Thing” backwards. That’s Gigli. This film has a 6 percent on Rotten Tomatoes, which means they were doing something so wrong that it felt right. It also stars Al Pacino and Christopher Walken. I will not be elaborating on their roles. —Justin Kirkland
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36. “Lifestories: Families In Crisis” A Body To Die For: The Aaron Henry Story (1994)
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Fine, it wasn’t released theatrically. Fine, it’s not technically a movie. Fine, it’s like thirty minutes long. But this episode of HBO’s entry into the Afterschool Special space is Ben’s first proper starring role, and it is therefore worthy of appreciation. He stars as a high school football player under pressure to perform, who decides to beef up by using steroids, immediately Hulks the fuck out, and is on his bedroom floor pleading for God’s mercy–writhing, pounding, acting–quicker than you can say the project’s full title. It’s a big opportunity for our guy, and he eats. (He eats steroids.) It’s tight, its credit sequence is very Saturday Morning All-Star Hits, and it has four colons in its name. —Dave Holmes
35. Changing Lanes (2002)
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This solid twist-of-fate thriller was a change-up for both Notting Hill director Roger Michell and for Affleck, who at this point in his career had rarely played characters who resided in the shades-of-grey moral middle ground. The reason it works as well as it does is because Affleck’s costar, Samuel L. Jackson, seems to challenge him to raise his game. A string of coincidences involving a car accident on the way to the courthouse pushes the limits of credulity, but it works well enough to pit the two actors against one another in an escalating cat-and-mouse game of revenge. Affleck cranks his smarm to eleven, but also shows us a glimmer of humanity beneath his shark’s exterior. Changing Lanes sort of came and went when it was first released, but it’s worth a revisit to see Affleck and Jackson square off. —CN
34. Forces of Nature (1999)
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For a while there at the tail end of the ‘90s, it looked like our man Ben was going to be Hollywood’s next romantic leading man. The animal crackers scene with Liv Tyler in Armageddon was the match that lit that particular fire. But the real test case came with this limp screwball comedy in which Affleck was paired with Sandra Bullock as a pair of meet-cutes who meet on his way to get married to Maura Tierney. Affleck + Bullock (in kooky mode, no less) must have sounded like a sure-fire hit in the pitch meeting. But, on celluloid, it didn’t quite work. The two meet-cutes start to fall for one another during rain gales and hail storms as he tries to get to the church on time. Unfortunately, their chemistry is even worse than the script. This one is waterlogged through and through. –Chris Nashawaty
33. Bounce (2000)
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Coming off his indie triumph The Opposite of Sex, Don Roos wrote and directed this romantic…tragedy? Affleck and Gwyneth Paltrow are at the end of their real-life relationship in this one, playing a cocky advertising executive and the widow he falls in love with. Oh, but Affleck has a secret: he swapped airplane tickets with Paltrow’s husband, putting him on the flight that crashed and killed him. It’s actually less fun than it sounds, and among the lesser of Affleck’s many, many cocky on-screen alcoholics. –DH
NO VOTES! The Indie Boi Years
For a few years in the ‘90s and early ‘00s, between School Ties and the moment when we came to a collective understanding that it was AFFleck and not afFLECK, Ben took his chances with a few independent films, and…well, not every bet pays off. In 1995’s Glory Daze he plays a misanthropic hipster on the eve of his college graduation and answers the question “what if there were a version of Noah Baumbach’s Kicking and Screaming in which it was impossible to like any of the characters?” In 1997’s Going All The Way, which co-stars ‘90s indie uber-boi Jeremy Davies, he goes full matinee idol as a returning Korean War veteran. And then in 2003, he appeared in the Miramax production The Third Wheel, in which, I don’t know, he has a goatee and owes Harvey Weinstein a favor. We’d say these movies came and went, but we have no clear evidence that they came. (The Third Wheel is available for rental on AppleTV+ and Amazon, the other two are lost forever.)
32. Phantoms (1998)
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The year after Good Will Hunting dropped, Burgeoning Ben appeared in three feature films. One was Armageddon, in which he showed us his skill mimicking an Australian accent and championing the erotic qualities of animal crackers. Another was a bit part Shakespeare in Love which went on to win best picture at the 1998 Academy Awards. The last was Phantoms, an adaptation of a Dean Koontz novel about a small ski resort town terrorized by a murder-ghost. Ok. So. The movie was rightly savaged by critics—Roger Ebert gave a one-star rating—and comatose performances by Peter O’Toole (wait what?) and Liev Schreiber (natch) don’t do much to prop up a script riddled with plot holes. Look I’m not here to bury Phantoms, but instead to praise a baby-faced Ben who, as the sheriff of Snowfield, Colorado hams his way through the one hour thirty six minute run time alternating between mock seriousness and sporting an enormous shit eating grin, elevating it into a film that’s not quite lowbrow brilliant but also something you wouldn’t mind being played at your local bar with the sound turned down. As it turns out Jay and Silent Bob were indeed right: Affleck was the bomb in Phantoms, yo. —Daniel Dumas
31. To The Wonder (2013)
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Terrence Malick is one of American cinema’s great artists, so Affleck’s desire to collaborate with him on To the Wonder–the director’s 2012 follow-up to his critically hailed The Tree of Life–seemed like a surefire bet. What the actor probably didn’t realize, however, is that the acclaimed auteur would ask his headliner to perform without dialogue for almost the entirety of the 112-minute feature, save for voiceover that helps drive this tale about the up-and-down romance shared by an American traveler and a divorced Ukrainian single mother (Olga Kurylenko), which is complicated by the former’s relationship with an old friend (Rachel McAdams). Malick’s film boasts plenty of twirling, all of it shot beautifully by Oscar-winning cinematographer Emmanuel Lubezki. Yet no amount of lovely aesthetics can chance the fact that this lyrical endeavor is dramatically inert, and that goes double for Affleck’s turn, which is mainly comprised of amorous and forlorn posing that takes minimal advantage of the star’s charm. –Nick Schager
30. Jay And Silent Bob Strike Back (2001)
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The Jay and Silent Bobiverse (known parochially as the View Askewniverse) is vast and deep, and while JASBSB is a classic, it’s no Clerks or Dogma. (You should also watch those, along with Chasing Amy before attempting this one.) This movie also loses points on this particular list because Ben Affleck’s inclusion is less a role to have any fun with than it is a comment on his ubiquity. He plays Holden, the creator of the Jay and Silent Bob characters, as well as a version of himself, Ben Affleck, star of this list. It’s a lot to take in, but if you’re a fan of movies about movies, it’s the perfect flick. -Kevin Sintumuang
29. 200 Cigarettes (1999)
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MTV Productions tried to make a modern-day American Graffiti, and…well, they nailed the casting. The movie gets early-career Kate Hudson, Casey Affleck, Paul Rudd, Janeane Garofalo and Dave Chappelle, newly-young-adult Christina Ricci and Gaby Hoffman, post-SNL Jay Mohr, pre-LTW Nicole Ari Parker, and a slumming Courtney Love. Ben plays a bartender named “Bartender,” whose whole job is to be hot and elusive. He succeeds. It’s a double throwback: a very 1999 movie set on New Year’s Eve 1981, and just for that, it’s worth watching. (Good luck; it’s streaming nowhere.) –DH
28. He’s Just Not That Into You
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Ah, He’s Just Not That Into You. Nine people! Four(ish) love stories! One movie you’ve probably forgotten. Our man Benny plays a dude with commitment issues, who realizes that he very much needs to get over his commitment issues if he wants to marry Jennifer Anist—er, Beth. Affleck plays this dude, named Neil, to perfectly adequate A-list-romcom-lead standards. (I.e. somewhere between Timberlake and McConaughey.) “I need you to stop being nice to me unless you’re going to marry me after, ” Beth says. Aww, how cute. Sweet nothings like that are the foundation of any love story.—Brady Langmann
NO VOTES! Wait, These Happened?
We’re going to be honest with you: there are a few credits on Affleck’s IMDB page that we’re pretty sure are fake movie posters from the walls of Tracy Jordan’s dressing room. Daddy and Them is apparently a Billy Bob Thornton-Laura Dern romantic comedy– you know, one of those–that has a theme song by John Prine and Iris DeMent, and we don’t even remember that. 2007’s Man About Town went direct to DVD, which might disqualify it if we remembered it, but we don’t, so that definitely disqualifies it. He apparently starred opposite Justin Timberlake in 2013’s Runner Runner; maybe JT was too busy promoting The 20/20 Experience to tell anyone about it. Affleck is on his suit and tie shit on the poster for Live By Night, but as with co-star Sienna Miller, I’m looking right at it and it sparks zero recognition. The Last Thing He Wanted is a political thriller based on a Joan Didion book (!), co-starring Anne Hathaway (!!) and directed by Dee Rees (!!!), but it was released in January 2020 and must have been washed out of our temporal lobe by Covid panic. There is no shame in this. Not every single movie is going to stick. Sorry to this man. (Man About Town is on Amazon and AppleTV+, The Last Thing He Wanted on Netflix, Runner Runner on Amazon, Hulu, HBO Max.)
27. Paycheck (2003)
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Has a movie title ever been more on the nose? In this soulless sci-fi potboiler, Affleck takes the money and runs as fast as his feet will take him. Paycheck is a terrible movie. It’s almost impossible to believe that it was directed by John Woo and based on a Philip K. Dick short story. Still, even if Paycheck was a masterpiece (which, again, it most certainly is not) it would have arrived with the stink of Gigli attached to it since it was Affleck’s first film after that notorious trainwreck. Big Ben does what he can as a hot-shot reverse engineer who’s hired to do some corporate dirty work and then get his memory of the dirty deed’s details erased for a hefty fee, but the biggest sin of Paycheck is just how aggressively bland the whole thing is. After watching it, you’ll probably want your memory erased too. –CN
26. Dogma (1999)
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What more basic cinematic pleasure is there than watching Ben Affleck and Matt Damon in a movie together? I’d wager: watching them play two “fallen angels” trying to make their way back into the big man’s good graces as sort of mirror images of one of cinema’s other great duos, Jay and Silent Bob. To boot, the movie is a great primer on religion if you grew up outside the church and a greatest hits list if you grew up in it. There’s no point in summarizing the plot; it would be like summarizing the Bible itself. Chaos begets more chaos, heathens lie with heathens. A perfect movie to watch while feeling stoned and sacrilegious. —Kelly Stout
25. Triple Frontier (2019)
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Arguably the most notable aspect of J.C. Chandor’s 2019 action-thriller is that it’s the production that begat the beach-photo revelation about Affleck’s glorious rising-phoenix back tattoo. Nonetheless, there’s a bit more to this Netflix venture than just its star’s infamous ink. Pairing Affleck with Oscar Isaac, Pedro Pascal, Charlie Hunnam and Garrett Hedlund, Chandor’s tale concerns a group of ex-military buddies who reunite to rob a narcotics kingpin, and while most of its characters have been conceived in strictly one dimension, Affleck receives the lion’s share of meaty material with which to work. As a divorced father convinced that this job will help him stay close to his kid, the actor turns out to be the surprising center of Chandor’s gritty morality play. There isn’t a lot of meat on this conventional genre effort’s bones, but Affleck invests his protagonist with a sweaty desperation and dogged greed that curdles in unexpected fashion. Consequently, he proves to be the most engaging facet of this macho saga. –NS
24. State of Play (2009)
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A political thriller that’s also a journalistic whodunit is the ultimate Hollywood twofer, but not since All The King’s Men has a movie successfully pulled one off. State of Play comes close thanks to Affleck’s portrayal as Stephen Collins —a rising star politician with one too many secrets to keep. Acting alongside Russell Crowe (in peak scruffy form as an aging newspaper reporter), Affleck doesn’t miss a beat, even as all the lies begin to undo his character’s career. There might be one too many sensational plot twists in State of Play, but thanks to Affleck’s understated performance, the film still goes down easy. –Abigail Covington
23. Hollywoodland (2006)
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After his long season in hell as a tabloid casualty, it was getting difficult to take any new Affleck movie seriously. He had become a punchline. The only way back, it seemed, was to walk the stations of the cross, take his lumps, and somehow remind everyone that he was a pretty decent actor. Well, that chance for redemption finally came with this juicy mystery about the life and death of George Reeves, the B-movie actor who played Superman on television in the ‘50s. A shroud of doubt has always swirled around Reeves’ death—did he commit suicide or was he murdered? And Affleck juices that old Tinseltown whodunit with just the right amount of anxiety, self-loathing, and faded glamor. Hollywoodland couldn’t have come at a better moment in Affleck’s EKG-like career arc. It was exactly the reminder everyone (and probably most of all, himself) needed to prove once and for all that he was an actor first and a National Enquirer punching bag second. –CN
22. The Sum of All Fears (2002)
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In college I had this schtick where my dirtbag friends and I would sneak a thermos filled with 151 rum into the theater and play drunk movie bingo. One day we went to see The Sum of All Fears and I had to take a pull every time Ben looked confused by basic plot points in the film. (Let’s just say I wasn’t able to walk out under my own power.) Twenty years hence this is what I recall from that Tuesday morning matinee. Ben plays CIA analyst-nerd Jack Ryan who is dispatched by Morgan Freeman—portraying either the director of the CIA or maybe the president of the United States—to help stop a nuclear weapons deal between some very bad dudes and the newly elected president of Russia who is not Vladimir Putin but is also kinda Vladimir Putin. Things go totally loco when the bad dudes steal a nuclear bomb and—I’m not kidding—use it to completely destroy Baltimore. I thought this was a vast improvement for the city but many characters in the movie (including Ben) did not. Anyway! Things get real fuzzy for me after this but I’m pretty sure Ben uses his analyst-nerd skills to save the day and prevent World War III. This brings me to the following conclusions: 1. Tom Clancy adaptations are best enjoyed with a large format container of high proof liquor. 2. In light of current events I hope the United States government employs an entire army of Ben Affleck-like analysts-nerds. —DD
21. The Accountant (2016)
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A mere seven months after debuting as Hollywood’s newest and nastiest Batman, Affleck again switched into dual-identity crime-fighting mode with The Accountant, director Gavin O’Connor’s thriller about an expert forensic accountant named Chris who spends his days exposing criminal financial malfeasance, and his nights executing the worst of the worst as a hired assassin. Basically, he’s the Dark Knight if the superhero was a geek whose greatest weapon was his autistic mind. This plays as ridiculously as it sounds, in part because Affleck takes his role very seriously, imbuing Chris with ruthless intellectual and physical precision. Trained in martial arts, an admirer of classic art, and bestowed with a Robin Hood-ish desire to take from the rich and give back to the poor, he’s an amalgam of numerous characters audiences have seen before. Though Affleck’s stoic turn contributes to the material’s cartoonishness, there’s also considerable pleasure to be had from his no-nonsense routine as a butt-kicking number-cruncher. –NS
NO VOTES! The Lesser Superheroes
Our Ben never did seem comfortable behind a mask, and with that face, neither would you. 2003’s Daredevil made $180 million globally, not enough to convince him to do a sequel. “Wearing a costume was a source of humiliation for me,” Affleck said at the London premiere of Hollywoodland, “and something I wouldn’t want to do again soon.” He did it again, as Batman in 2016’s 2.5 hour endurance event Batman v Superman (which made the list), then followed up a Suicide Squad cameo with Justice League (which did not, at least in its original form), and then he got fed up and quit The Batman. I guess the good news is that he cleared the way for Robert Pattinson?
(The DC movies are on HBO Max, Daredevil is on Hulu)
20. Reindeer Games (2000)
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Few directors have boasted a more strikingly muscular visual style than John Frankenheimer (The Manchurian Candidate, The Train, Seconds, Ronin), and that remained true with his cinematic swan song, 2000’s Reindeer Games, which also features a compellingly gung-ho performance from Affleck as an ex-con who assumes his dead cell mate’s identity in order to get with his girl (Charlize Theron), only to wind up embroiled in a dangerous casino heist. This is brazen B-movie territory, handled with all the insane plot twists and over-the-top scenery-chewing that one might expect. The pulp is thick, and Affleck seems perfectly comfortable wallowing in it, radiating a cocky tough-guy charisma that’s consistently winning even when the story threatens to drive off a cliff (both figuratively and, ultimately, literally). No one will ever give the actor an award for indulging in such down-and-dirty genre fare, but there are few early Affleck efforts that remain as amusingly entertaining as this one. –NS
19. Shakespeare In Love (1998)
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Maybe this one would be higher up if there had been more Ben. Gwyneth Paltrow has claimed that Harvey Weinstein wanted Affleck to play William Shakespeare in this one, to which she insisted they get a proper Brit. Instead, he gets an extended cameo as Ned Alleyn, the greatest actor of his generation, and the accent does not exactly work, but the swagger absolutely does. This film won Best Picture, but more importantly it introduced him to Paltrow, whom he dated for three years, thereby kicking off the Tabloid Era of Ben Affleck. –DH
18. School Ties (1992)
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Affleck’s proper movie debut, alongside a veritable Abercrombie & Fitch catalog of fellow newcomers: Chris O’Donnell, Brendan Fraser, Cole Hauser, Randall Batinkoff, and future collaborator Matt Damon. It plays like a Very Special Episode of Dead Poets Society, focusing on anti-semitism among the young American elite. Affleck doesn’t have much to do here beyond being handsome and vaguely menacing, but he’s good at that. Fun fact: the screenplay was written by Dick Wolf, who was then in the early seasons of a struggling NBC police procedural called Law & Order. –DH
17. Mallrats (1995)
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Ben Affleck has played a lot of sleazy guys over the course of his career, but none of them hold a candle to the O.G. of sleaze—Mallrats’ villain Shannon Hamilton. What a d-bag. Affleck aces the role of Hamilton, outfitting the manager of the famed Eden Prairie Mall’s Fashionable Male clothing store in an infuriating sense of entitlement that makes the character’s inevitable downfall all the more rewarding. Mallrats marks Affleck’s first collaboration with Kevin Smith, who himself was just getting started on building out the View Askewniverse when Mallrats was released (and went straight to video) in 1995. Since then, both gentlemen have gone on to make bigger and more important films, but Mallrats still reigns as the most fun. —AC
16. Zach Snyder’s Justice League (2021)
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Affleck’s turn as a jaded, middle-aged Batman is oddly spot on in a life-imitating art kind of way—it’s Sadfleck as Bruce Wayne. Zach Snyder’s Justice League gives Batfleck extra broodiness, overshadowing the zingers of the Joss Whedon version of the film. Appropriately, Affleck retired from the role for very Sadfleck reasons, calling it a “nadir” experience and saying “I didn’t like being there.” But he did return to shoot one last scene with Jared Leto’s Joker. It didn’t take much for Affleck to don the cowl again. Snyder called him and said “Listen, bro…I think it’d be cool to see” and Affleck was like, “Yeah bud. For you, I’ll do it.” —KS
15. Deep Water (2022)
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Ben’s Deep Water role is a tricky one to rank. Why? Because it falls squarely into that guilty pleasure grey area, where the line between ridiculousness and greatness gets mighty blurry. Based on a kinky Patricia Highsmith story, Adrian Lyne’s throwback to his ’80s erotic thriller heyday (9 1/2 Weeks, Fatal Attraction) stars Affleck as a super-rich, morally shady brainiac with two obvious weaknesses: his fondness for collecting snails (metaphor alert…or just plain eccentricity for eccentricity’s sake?) and his strange devotion to his red-hot, openly philandering wife (Ana de Armas). Lyne toggles between steamy sex scenes and jealous rage like a horny virtuoso while we are left to guess if Big Ben, beneath his seemingly placid demeanor, is man enough to possess a vengeful, murderous dark side (take a wild guess). By any standard metric, Deep Water is trash. But it’s the kind of trash that knows exactly what it’s doing and succeeds on its own ludicrously tawdry terms. —CN
14. Batman v Superman: Dawn of Justice (2016)
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Many men have donned the cape and cowl as Gotham’s nocturnal vigilante, and while Affleck’s maiden outing as the crime-fighter wasn’t particularly well-received by critics or audiences, Batman v Superman: Dawn of Justice’s underwhelming showing ultimately had little to do with his performance. Playing an older, grimmer Batman–so angry he actually brands his victims!–Affleck exudes a measure of gravity and fury that’s in tune with the dour atmosphere of Zack Snyder’s would-be DC Comics epic. Pitted against Henry Cavill’s Man of Steel, this Batman is as physically stout as he is obsessively determined, driven by resentment over the Kryptonian interloper’s god-like power, and rage at his apparent indifference to humanity’s plight. There isn’t a lot of humor to this portrayal of the iconic crusader; instead, Affleck infuses the character with a bone-deep weariness over lost lives and seemingly unwinnable wars. He’s the glue that holds Snyder’s sprawling, uneven film together–a borderline-heroic task itself. –NS
13. Pearl Harbor (2001)
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In which Michael Bay throws a couple hundred million dollars at the screen in an attempt to tell his version of America’s day that will live in infamy. This is an epic that encapsulates everything that was wrong with Hollywood in 2001. The Japanese bombing of Hawaii is treated as little more than an exotic backdrop for a love-triangle soap opera involving Josh Hartnett, Kate Beckinsale, and Big Ben. Solemn history and Bay’s sizzle-reel approach to filmmaking turn out to be predictably strange bedfellows, while Affleck’s Tennessee flyboy just gets lost amidst all of the big-budget shock and awe folly of it all. Pearl Harbor is proof that the road to cinematic hell is paved with good intentions. –CN
NO VOTES! The Sub-Smiths
At the risk of alienating the View Askew-niverse, Kevin Smith’s creative output is uneven in quality, even when Ben Affleck is involved. Sometimes they make what for Smith is a mass-appeal movie, like Dogma, sometimes they give you the Jay and Silent Bob Reboot nobody asked for. Bad Gigli press and end-of-Bennifer buzz doomed Jersey Girl at the box office, and eighteen years later nobody here included it among their favorites. And finally, while Smith made his name with Clerks, Clerks II didn’t connect with our culture crew, and our research indicates a Clerks III is on the way. Most tragically, any talk of Kevin Smith reminds us of that tweet– YOU KNOW THE ONE– so let’s change the subject. After this…
(Reboot is on Amazon and AppleTV+, Jersey Girl on Amazon, AppleTV+, and HBO Max, Clerks II is on Amazon)
12. Chasing Amy (1997)
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25 years later, and Chasing Amy still bamboozles the queer community. Is it an ahead-of-its-time and provocative portrait of bisexuality? Or a tonedeaf film that both invalidates and overtly sexualizes the lesbian experience? It’s both and neither. Mostly, it’s a film about a geeky dude named Holden, played by a young goateed Ben Affleck, who lets his insecurities ruin a relationship with a pretty rad comic book writer, played by ‘90s alternative it girl, Joey Laurence Adams. For all of its problematic optics, Chasing Amy will always be right about one thing: proposing a threesome will not help you win back your ex—sorry Holden. —AC
11. Boiler Room (2000)
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A not-bad cautionary tale released on the heels of the bursting of the dot.com bubble, novice writer-director Ben Younger’s morality play stars Giovanni Ribisi as a gullible, ambitious young turk who fleeces folks by pitching them junk stocks from a testosterone-drenched Long Island chop-shop brokerage full of macho banter and musky pheromones. Like Alec Baldwin in Glengarry Glen Ross, Affleck gets the flashiest role as the alpha-recruiter who initiates new salesmen by questioning their manhood and barking Mametian arias of motivational snake oil. Needless to say, the role fits him as perfectly as a bespoke Armani suit. He steals everything that’s worth stealing in the movie. –CN
10. The Way Back (2019)
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The Way Back drew the short stick. Ben Affleck’s startlingly personal basketball film, where he plays a high school coach struggling with alcoholism, debuted on March 1, 2020. It’s the last film I saw in theaters, you know, before everything. I think, obviously, a hell of a lot more people would’ve seen The Way Back if it premiered in 2019, or 2023, because it’s one of Affleck’s best films. He pulls off the pain of a burnout who keeps getting in his own way. More than that, The Way Back is a throwback to a lost era of sports movie—the Remember the Titans days of the ’90s and ’00s, where filmmakers weren’t afraid to be shamelessly inspirational. Maybe it’s the film we needed during the pandemic. Instead, we got it two weeks early.—BL
9. The Tender Bar (2021)
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All the elements that make Ben Affleck Ben Affleck– the sleepy-eyed charm, the self-conscious swagger, the chin– come together in this adaptation of JR Moehringer’s 2005 memoir, and serve his character perfectly. As Uncle Charlie, the book-reading, bartending, sometimes blunt father figure in JR’s life, Affleck gives a lived-in, relaxed performance and makes you thirsty for a whiskey on the rocks. You might not take his advice, but you can’t take your eyes off him. It’s a testament to his performance here that I don’t remember much else about the movie. –DH
8. The Last Duel (2021)
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There comes a point in an A-list actor’s career where their fame eclipses their talents, meaning that no matter how excellent their performances may be, it’s impossible to see anything but the guy from the tabloids. For me, Affleck crossed that threshold a long time ago, but in The Last Duel, he redeemed himself. Affleck is the best he’s been in years as Count Pierre d’Alençon, a bawdy, boorish medieval nobleman hellbent on destroying Matt Damon’s life (the Count gleefully dismisses Damon’s character as “fucking boring”). Sporting a bleach-blonde bowl cut and a goatee to match, Affleck is unrecognizable, but it’s not just the get-up allowing him to melt into the role; it’s the way he completely gives himself over to this venal, imperious asshole, and steals every scene along the way. —Adrienne Westenfeld
7. AIR (2023)
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Affleck’s turn as Nike co-founder Phil Knight is less of a portrayal of the Nike legend himself and more of a caricature of Affleck himself. He’s running the show, telling some jokes, dishing out advice, and refusing to change his appearance to look like Knight in the slightest. But as everyone is running around and yelling into their phones like a chicken with its head cut off trying to land Michael Jordan’s coveted shoe deal, Affleck is the much-needed comic relief. He’s the head honcho of a multimillion-dollar company who quotes Buddha, doesn’t wear shoes in the office of his shoe company, and decides things on long runs. Somehow, it’s one of the best roles he’s ever played.—Josh Rosenberg
6. Armageddon (1998)
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I will not make this entire entry about the scene where Ben Affleck walks an animal cracker, seductively, up Liv Tyler’s torso while speaking in an Australian accent. I should, but I won’t. I will however include a link to the video because it is cinema at its peak. Armageddon is a perfect film, in a lot of ways. Not perfect in the sense that it was robbed of Oscars, but perfect in that when you’re hungover at 2pm on a Saturday, finding Armageddon playing on TBS feels like you’ve hit the lottery. Armageddon is the peak of disaster films. Starring Affleck, Tyler, Bruce Willis, Billy Bob Thornton, and Steve Buscemi (??), a team of ragtag drillers and experts must intercept an asteroid, blow it up, and save the world. It’s pretty straightforward, but when you fold in the melodrama and the perfect movie song from Aerosmith, what you have here is a type of film that they simply don’t make anymore: good, pulpy, end times fun that is meant to entertain the pants off of you. —JK
NO VOTES! The Simply Unloved
Jason Bateman ketamine comedy Extract failed to excite our judges the way the words “Jason Bateman ketamine comedy” excited you just now. 2004’s Surviving Christmas was nominated for the Worst Picture Razzie Gigli had won the year before, but even the very healthy urge to wedgie those Razzies assholes wasn’t enough to get it on the list. (It lost to Catwoman, obviously.) In 2010, The Company Men brought Affleck back to his native Boston, got a limited theatrical release for Oscar qualification, got no nominations, and got one fewer vote from our culture team than Gigli did, which is to say none. Still an excellent career, Ben. Please don’t smoke dejectedly over this.
(Extract is on Amazon, AppleTV+, HBO Max, and Hulu, Surviving Christmas did not survive to the streaming age but it and The Company Men are available for rent on AppleTV+.)
5. Dazed and Confused (1993)
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Richard Linklater’s Foghat-fueled ode to being a Texas teen on the eve of the American Bicentennial is one of the greatest coming-of-age stories ever made. The casting is prescient lightning in a bottle, the characters are fully realized rather than two-dimensional cartoons, and the time and place are so vivid you can almost taste the stale beer and smell the skunk weed. As the film’s resident upperclassman bully O’Bannion, Affleck delights in beating on pipsqueak freshmen because…well, because he can. Affleck shows the audience the sparkle of sadistic glee in his character’s eyes, but if you squint hard enough, you might also be able to make out the sweaty insecurity of someone who’s trying to compensate for some unspoken psychological wound. Either way, he’s a total asshole—a type Affleck can play in his sleep. Like Matthew McConaughey’s scene-stealing Wooderson, Affleck is hardly the film’s main character, but he knows exactly what to do with every second of screen time he’s given. –CN
4. The Town (2010)
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Ben Affleck’s second-most Boston film. (Scroll to No.1 to see his greatest homage to the Athens of America.) Except this one features gruffer accents, a high stakes heist, and, in the case of Blake Lively, thicker eyeliner. As director, Affleck reached for a heady meditation on the culture of crime. It’s not totally unappreciated but that’s not exactly what makes this film good. Nah, here, it’s all about the stakes. Will Claire discover Doug’s past—or worse, his present? Can Doug out-run his life? How the hell are they gonna shoot their way out of Fenway?? —Madison Vain
3. Argo (2012)
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At first the details of this story sound too insane to be true. During the 1979 Iran hostage crisis a group of American diplomats managed to slip out of the US Embassy and find cover at the Canadian Ambassador’s residence. They can’t stick around in Iran—if they’re captured it’ll mean blindfolds, beatings, and bullets. The CIA hatches a scheme: have the diplomats pose as a fake Canadian film crew for an even faker low budget sci-fi movie, head to the airport, and catch the first flight out of town. To complete the ruse, the CIA sets up a mock production office, writes a feature length script, and even enlists famed comic book artist Jack Kirby to illustrate the storyboards. Affleck pulls a double shift as director and as Tony Mendez, the career covert operative charged with leading the diplomats out of the country. Behind the camera Ben never lets his foot off the gas, ratcheting up the tension with a mix of harrowing action sequences and high pressure set pieces that make it feel like the entire thing could unravel in the most catastrophic way possible. Affleck portrays Mendez with quiet focused intensity, all too aware of what could happen should his mission fail. While there are some scenes that were invented for the sake of dramatic effect—hello tarmac chase—the two hour run time rips by so breathlessly it’s easy to see why Argo is the reason Ben has twice the number of Oscars than Matt. —DD
2. Gone Girl (2014)
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As someone who hails from Missouri, I cherish this opportunity to have my home state be the setting of such a highly regarded film. Unfortunately, that sick house surrounding Lake Ozark, belonging to the character Desi—which we only see for a few moments before well, you know—is the only thing that looks good in this dark thriller. Everyone else is a liar, a cheater, or totally psychopathic. But boy is Ben good at this lane of man! He plays a louche with such weight—such an intoxicating blend of defensiveness, regret, and whoopsie-daisy that, while you never can quite decide if you’ll root for him, you cannot look away. —MV
1. Good Will Hunting (1997)
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Affleck has had quite a career, but when you put together a list of his best films, how can Good Will Hunting not be at the top? Penned with Hollywood best friend Matt Damon, it scratches all the itches of an Affleck classic: Boston-set, scrappiness as an endearing quality, and a wise older figure who is able to guide a young man out of a difficult situation. (Thought: Armageddon should have been set in Boston.) With all the key components in place, all that’s left is to fill this brilliant screenplay with heart. For those who have somehow not seen the film, Good Will Hunting follows Will Hunting, a brilliant self-taught genius who is a janitor at Boston’s MIT. Naturally, after a good ol’ Boston brawl, Hunting can escape jail if he applies his savant-like mathematics skill and attends court-mandated therapy. Through both, he reveals his true potential. And in the process, Affleck, Damon, and Robin Williams give the performances of their careers. —JK
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