30. PEARL HARBOR (2001)

In the wake of Titanic, numerous movie studios tried to boil its success down to “Real-Life Disaster + Doomed Romance = Massive Hit,” and all flopped. Probably the most public of those failures was this love triangle between Affleck, Kate Beckinsale, and Josh Hartnett that hoped extensive CGI would negate Pearl Harbor’s overall insensitivity.

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29. TO THE WONDER (2013)

Director Terrence Malick (The Thin Red Line, The Tree of Life) is known for laborious pictures that reward stamina with stimulating thoughts, but To the Wonder has nothing to actually say, leaving Affleck to do his best with an angry script draped in wondrous cinematography it doesn’t deserve.

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28. SMOKIN’ ACES (2007)

Like The Boondock Saints and Donnie Darko before it, Smokin’ Aces really isn’t that good of a movie, but hides that fact through such striking filmmaking that it’s gained a rather defensive cult following. To say anything about Affleck’s character would be to give away an excellent trick of the film’s, but he does wonders with his role. A key scene involving a meeting with two bail bondsmen is shocking in all the best ways.

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27. JAY AND SILENT BOB
STRIKE BACK (2001)

At once a great movie and a mediocre one (depending on your knowledge of earlier Kevin Smith movies), Jay and Silent Bob Strike Back was Ben Affleck’s Dr. Strangelove, giving him the opportunity to not only reprise his Chasing Amy character but also play a sharply self-deprecating version of himself on the fake set of Good Will Hunting 2: Hunting Season.

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26. FORCES OF NATURE (1999)

As far as romantic comedies go, Forces of Nature is fine. As far as late-‘90s romantic comedies go, it’s better than average. Affleck and Bullock deserve most of the credit, though the script does take a smartly unexpected turn that deserves its own merit for not going where you’d expect.

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25. DADDY AND THEM (2001)

Whether you like Daddy and Them or not — and some really don’t — you have to admire its uncompromising tastes. At once a sharp slice of Southern culture, a dark comedy, and a memorable portrayal of rural family, it’s the removed cousin of The Royal Tenenbaums and Nebraska in many ways. Affleck and Jamie Lee Curtis steal every scene of theirs as a bickering married couple.

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24. THE SUM OF
ALL FEARS (2002)

The Sum of All Fears, like a bunch of Ben Affleck movies around this period, was unfairly judged when it first came out. While it may lack the suspense of The Hunt for Red October or the complexity of Clear and Present Danger, it’s considerably better than the downright dumb Patriot Games. Affleck’s not as memorable as previous Jack Ryan portrayers, but he holds his own as the George Lazenby of the series.

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23. ARMAGEDDON (1998)

Even the worst directors can make good movies, and while Armageddon is by no means amazing, it’s successfully entertaining in all the medium-aiming ways it intends to be. Affleck and Bruce Willis lead a wonderful ensemble cast in one of the bigger save-the-world movies that crashed into theatres near the end of the millennium.

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22. DAREDEVIL (2003)

Yes, the Netflix series is better. And sure, the 2003 movie is a more mainstream take than many Marvel fans wanted. But the acting in Daredevil is fantastic and a lot better than you probably remember. Affleck has true chemistry with Jennifer Garner (what with them falling in love during filming), and Colin Farrell and Michael Clarke Duncan ham their roles up just enough while remaining menacingly crazy villains.

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21. GOING ALL THE WAY (1997)

While Mark Pellington, taking his first step into features after a portfolio of music videos, has some trouble reigning himself in here, Going All the Way remains a powerful story of two very dissimilar young men who become friends after being discharged from the Korean War. Affleck is good, but overshadowed by the outstanding Jeremy Davies (who would go on to reinvent his character into Daniel Faraday on Lost).

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ON THE NEXT PAGE: Gone Girl, Jersey Girl, and Dazed and Confused…