10. CHANGING LANES (2002)
A car accident involving two men racing to important court meetings derails both of their lives. Affleck’s and Samuel L. Jackson’s characters both blame each other for their troubles, which escalate into bigger and bigger stakes in more and more brutal acts of petty revenge. What makes Changing Lanes work so well is how fairly it depicts the two desperate men, never choosing sides and never painting either as blameless.
9. HOLLYWOODLAND (2006)
After most of the world had given up on Affleck ever being anything more than a punchline, Hollywoodland was the first step of his eventual return to form. Affleck was nominated for numerous awards for his portrayal of original Superman actor George Reeves, and for good reason: he used his own experiences of being adored and then discarded by the American public to tap into a very real place.
8. STATE OF PLAY (2009)
Six years before playing a reporter in Spotlight, Rachel McAdams did so with Russell Crowe in State of Play. Affleck is a very flawed congressman who calls upon Crowe’s investigative journalist to look into the death of one of his staff members (and his mistress) after the police rule it a suicide. The talented cast has great fun with the script’s labyrinthine twists and turns, and the direction is nearly flawless.
7. CLERKS II (2006)
A truly special sequel — one very nearly the equal of its originator — Clerks II is the most insightful look at modern adults growing dissatisfied with their disillusioned lives this side of Before Sunset. Comedy that ranges from broad to esoteric dances comfortably here with real drama and emotion in a pitch-perfect bookend to Kevin Smith’s 1994 debut. Affleck’s appearance in it may be brief, but his credited role as Gawking Guy (as opposed to an uncredited cameo) does, indeed, make it a Ben Affleck movie.
6. SHAKESPEARE IN LOVE (1998)
The first Best Picture winner of Affleck’s (but not his last), Shakespeare in Love is known these days more for having beaten out Saving Private Ryan (featuring none other than Damon) for the Oscar, but it deserved the prize just as much. One of the most cleverly crafted screenplays of the ‘90s is done true justice by a cast including Joseph Fiennes, Gwyneth Paltrow, Geoffrey Rush, Tom Wilkinson, Judi Dench, and Affleck as a self-absorbed actor.
5. THE TOWN (2010)
Those that dismiss The Town as nothing more than a re-tread of Heat are missing how much authentic truth, ugliness, character, courage, and emotion is pulsing through every scene of this crime thriller. After learning the ropes behind the camera with Gone, Baby, Gone, Affleck toggled between writing, directing, and starring here and handles it with aplomb.
4. GOOD WILL HUNTING (1997)
As attractive as the fairy-tale story behind Damon and Affleck’s creation of Good Will Hunting is, it wouldn’t count for much if the movie weren’t worthy of the backstory. Nearly 20 years later, though, it remains the gold standard for actors writing themselves better roles than they can get in auditions. Damon’s performance here remains one of his best, as does Robin William’s Oscar-winning work, but Affleck holds his own completely, walking away with one of the best monologues of the late ‘90s.
3. CHASING AMY (1997)
Affleck’s greatest performance to date is in the heart-achingly powerful romance Chasing Amy. Wanting to get back to his personal roots after the poorly received Mallrats, Kevin Smith came back from the drawing board with a movie that feels intrusive to watch at times, purely for how natural and personal the characters’ story feels. Affleck’s Holden struggles to cope in a relationship with a woman whose sexual experience and tastes trigger possibly insurmountable insecurities and doubts in him.
2. ARGO (2012)
When it comes to climaxes with tension almost too thick to see through, Argo has possibly the most suspenseful one since Se7en. The movie is a slow-burning fuse, taking the time to get to know not just Affleck’s CIA operative but also the six diplomats trapped in Tehran that he goes to save, making the situation the seven find themselves in while trying to escape Iran increasingly terrifying. It’s the best movie Affleck has shepherded, taking responsibility for Argo’s writing, directing, and producing — while still managing to also star as the lead character.
1. DOGMA (1999)
When it comes to comedies about religion, there are plenty of sharply satirical or judgmentally mean-spirited ones, but Dogma stands alone as one of the most provocative and intelligent comedies of the last 30 years, spiritually inclined or otherwise. An all-star cast of famous faces plays an assortment of fascinatingly interesting characters in Kevin Smith’s contemplation of what religion means for modern society. As Loki and Bartleby, two fallen angels using a Catholic loophole to try and get back in Heaven, Damon and Affleck are better together here than they’ve ever been. Moreover, Smith’s script forms one of the sharpest comedies of the ‘90s, finding time to debate the importance of ideas over beliefs in between jokes about Skee-Ball and McDonald’s.
Stay tuned this weekend for my review of Affleck’s latest, Batman v. Superman: Dawn of Justice.