64 men enter. One man leaves.
A few words on the criteria: I'm only taking into account performances from the past ten years (1997 and onward). Film and television performances count. Match-ups will be judged on the following merits: (1) number of performances I've enjoyed (sheer quantity); (2) whose singular best performance is the greatest (quality); (3) if I had an Oscar ballot, how many nominations would the actor have received since '97 (fake Oscars); (4) if both actors have co-starred in a film, who gave the better performance (spotlights stolen); and (5) since watching boys fight is something you can see at the closest downtown bar, this time around we're judging by who would prevail in the most time-tested of competitive activities: The Walkoff (Motherf*cking Walkoff).
Jeff Bridges vs. Ed Harris
Quantity: Okay, can we get Jeff Bridges in a good movie again? His last three credits are Surf's Up, Stick It, and Tideland. Can't fault him for a Gilliam collaboration, even if it did fail, but can the Coens call him up again or what? Even if Harris isn't stealing the show, he's been solid in supporting roles as of late (A History of Violence; Gone Baby Gone). Advantage: Harris
Quality: Bridges in The Door In The Floor and Harris in Pollock are both film-defining performances. Bridges gives the better one. Advantage: Bridges
Fake Oscar Nods: Bridges: 2 (The Big Lebowski; The Door In The Floor); Harris: 2 (The Truman Show; Pollock). Push
Spotlights Stolen: They were both in Masked and Anonymous, but I never saw it. Push
Motherf*cking Walkoff: They're very similar in terms of their propensity for working it. Both kind of old-man attractive but aloof about it. All things being equal, we'll once again give it to the Lebowski Strut. Advantage: Bridges
Winner: Jeff Bridges 2-1
Matt Damon vs. Jeffrey Wright
Quantity: Damon remains untouchable on the quantity scale, and I haven't even seen The Bourne Ultimatum yet. Jeffrey Wright has nothing to be ashamed of here. Advantage: Damon
Quality: Damon's strong collection of very good performances still doesn't produce something as great as Wright in Angels In America. Advantage: Wright
Fake Oscar Nods: Damon: 1 (The Departed); Wright: 0
Spotlights Stolen: They gave the two best performances in Syriana, with Wright's conflicted lawyer bested by Damon's oil...analyst? Sopkesmodel? What exactly did his character do for a living? No matter... Advantage: Damon
Motherf*cking Walkoff: Damon's the Sexiest Man Alive, sure, but he's still never gone drag. Advantage: Wright
Winner: Matt Damon 3-2
Billy Crudup vs. Brad Pitt
Quantity: The fact that I've yet to see The Assassination of Jesse James may or may not be my loss (I've heard enough divergent opinions to be utterly unsure as to how I'll respond to it), but it's certainly Pitt's loss here as it means he gets edged out by the star of World Traveler and Trust The Man. Ouch. Advantage: Crudup
Quality: Tyler Durden from Fight Club versus F*ckhead from Jesus' Son. If it were a fistfight, it would be such a hilarious mismatch that I'd pay full price to see it. As an acting battle, it's not quite that one-sided, but Crudup is still the clear winner. Advantage: Crudup
Fake Oscar Nods: Crudup: 3 (Jesus' Son; Almost Famous; Stage Beauty); Pitt: 1 (Fight Club.
Spotlights Stolen: Both played adult survivors of juvie abuse in Sleepers. Crudup managed to sell "strung-out vengeance" pretty well, but Pitt got more screen time and was slightly more impressive. Advantage: Pitt
Motherf*cking Walkoff: Difficult. You know Billy's my guy, but I suppose I'll have to bow down to popular opinion on some things. (No need to mention that I'm doing so only after the outcome is secured. I'm well aware). Advantage: Pitt
Winner: Billy Crudup 3-2
EDIT: Shame on me for failing to mention that the above face-off was a battle between the man originally slated to play Russell Hammond in Almost Famous and the man who eventually did play him, to much acclaim. Further proof that the right man prevailed here.
Hugh Jackman vs. Clive Owen
Quantity: It's kind of fascinating the way these two men's careers parallel each other. Both were packaged as action heroes in potential franchises (Owen with King Arthur and Sin City, Jackman in the X-Men movies), both worked for legendary directors like Woody Allen (Jackman in Scoop) and Robert Altman (Owen in Gosford Park), and both ended up on '06 "Best of" lists by working with two of the best directors of their generation (Jackman in The Fountain, Owen in Children of Men). It's no surprise that the ledger is balanced. Advantage: Push
Quality: The one thing that Owen has that Jackman doesn't is a performance like Owen's in Closer. He came into his own as an actor, in a big way, with The Fountain, but by that time Owen had already been there for a few years. And he'd done it (marginally) better. Advantage: Owen
Fake Oscar Nods: Jackman: 1 (The Fountain); Owen: 1 (Closer). Push
Spotlights Stolen: They've never shared the screen. Un-fucking-forunately.
Motherf*cking Walkoff: Oh my God, this is difficult. Usually, the walkoff goes to the most James Bond-like (Owen) or the better looking one (Jackman...by a nose). Of course, Jackman has the secret fancy-footed Peter Allen gay hoofer weapon going for him. Advantage: Jackman
Winner: 1-1 HOLY CRAP IT'S A TIE! Tough call, kids. Vote wisely and once.