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Oh, that Affleck!

by Tyler Wilson
| September 17, 2010 9:00 PM

Former laughing stock Ben Affleck is receiving some of the best reviews of his career for the leading role in this week's crime drama, "The Town." Affleck also co-wrote and directed the film, a follow-up to his stellar directorial debut, "Gone Baby Gone."

While his reputation behind-the-scenes remains perfect (he also won an Oscar for co-writing "Good Will Hunting"), Affleck's onscreen career has been, well, inconsistent at best. For every respectable entry, there seems to be a couple really embarrassing ones.

But even Affleck's once pitiful acting career has rebounded in recent years. Which performances stand out as his best? Here are 16 of his most noteworthy (and notorious) films thrown at each other NCAA tournament style.

Behold the Sweet 16 of Ben Affleck!

Bracket 1

Good Will Hunting (1) vs. Gigli (16)

To be fair, not enough people even saw Affleck's debacle with Jennifer Lopez to rank "Gigli" as one of Hollywood's biggest disasters. I, however, have seen the film, in its entirety, and it's definitely as terrible as you heard. Winner: "Good Will Hunting"

Armageddon (8) vs. Dogma (9)

In a battle between cheesy asteroid blockbuster and controversial religious satire, definitely go for the movie with Affleck wearing giant feathered wings. Winner: "Dogma"

Bracket Final

Good Will Hunting (1) vs. Dogma (9)

Matt Damon had the showier part, but Affleck is compelling as the math prodigy's best bud, Chuckie. Bonus points for Damon and Affleck's participation in "Good Will Hunting 2: Hunting Season," as seen in "Jay and Silent Bob Strike Back." Winner: "Good Will Hunting"

Bracket 2

Boiler Room (5) vs. Daredevil (12)

Affleck's supporting role is the best thing about "Boiler Room," an otherwise okay "Wall Street" wannabe. Affleck may have ignited the box office playing blind superhero Daredevil, but nobody liked the film enough to garner a franchise. Winner: "Boiler Room"

Hollywoodland (4) vs. Pearl Harbor (13)

Aside from the terrific bombing sequence, the nearly 3-hour "Pearl Harbor" is an unbearable amalgamation of bad dialogue and trite storytelling. In contrast, 2006's "Hollywoodland" is Affleck's comeback vehicle, and the actor earned universal praise playing TV Superman, George Reeves. Winner: "Hollywoodland"

Bracket Final

Boiler Room (5) vs. Hollywoodland 4)

Yeah, I'll say it: Affleck deserved an Oscar nomination for his work in "Hollywoodland." "Gigli" is forgiven, bud. Winner: "Hollywoodland"

Bracket 3

Chasing Amy (2) vs. Reindeer Games (15)

Few actors really understand the rhythms of Kevin Smith dialogue. Maybe that's why Affleck keeps working with the writer/director, especially since anchoring Smith's best work, 1997's "Chasing Amy." Even with Charlize Theron, Gary Sinise and director John Frankenheimer ("The Manchurian Candidate"), "Reindeer Games" is as stupid as the title suggests. Winner: "Chasing Amy"

State of Play (7) vs. Extract (10)

Affleck plays second banana to Russell Crowe in the entertaining newspaper saga, "State of Play" and manages to hold his own just fine as a slippery politician. In the little-seen comedy, "Extract," the actor plays drug-pushing best bud to Jason Bateman and lands the biggest laughs in the movie. Tough call. Winner: "Extract"

Bracket Final

Chasing Amy (2) vs. Extract (10)

Both are great performances, so give the edge to the juicier part. No, that wasn't meant to be a clumsy play on words. Winner: "Chasing Amy"

Bracket 4

Shakespeare in Love (3) vs. Phantoms (14)

The Oscar-winning "Shakespeare in Love" is a good movie, but not because of Affleck's supporting work. In the horror flick "Phantoms," however, Affleck rocks a hilarious cowboy hat for close to 90 minutes. Winner: "Phantoms"

Changing Lanes (6) vs. Jersey Girl (11)

Serious acting on both fronts. In "Changing Lanes," Affleck goes toe-to-toe with Samuel L. Jackson (in a movie where he isn't just playing Samuel L. Jackson). In "Jersey Girl," Affleck tries his best to anchor Kevin Smith's sloppy attempt at mature filmmaking, but the script lets him down with a series of melodramatic cliches in the final act. And gasp! Wasn't that Jennifer Lopez again as the pregnant wife? Winner: "Changing Lanes"

Bracket Final

Phantoms (14) vs. Changing Lanes (6)

Hilarious cowboy hats can only get you so far in life. Winner: "Changing Lanes"

Final Four!

Good Will Hunting (1) vs. Hollywoodland (4)

No matter what happened during his streak of duds in the early 2000s, Affleck's acting abilities have vastly improved in the nine-year gap between "Good Will Hunting" and "Hollywoodland." It's evident Affleck connected with the frustrations George Reeves faced after being typecast as the Man of Steel. His own struggles with celebrity add emotional weight to the performance. Winner: "Hollywoodland"

Chasing Amy (2) vs. Changing Lanes (6)

Again, this battle comes down to experience. "Chasing Amy" was an indie breakout with a strong script, and it took Affleck a few years to get comfortable in dramatic roles that demanded more of him. Too bad it took another four years after "Changing Lanes" for him to do it again. Winner: "Changing Lanes"

Finals

Hollywoodland (4) vs. Changing Lanes (6)

"Hollywoodland" for the easy win, although perhaps we shouldn't be encouraging Affleck to be working in front of the camera. Not when something like "Gone Baby Gone" exists, a movie directed with the precision of a distinguished veteran. Sorry, Ben. Your best bet at longevity is to stay behind the camera. Winner: "Gone Baby Gone"