Timothy Olyphant vs. Nicky Katt
Battle of the Small-Time Sleazebags

There are so few true screen bad-asses around anymore. Not only that, but as soon as they die, the mythos surrounding archetypal screen tough guys is punctured like a balloon. Wait, we're supposed to believe that Bing Crosby beat his children, and John Wayne was gay? How can that be?

Now that the Hollywood studio system has ceased manufacturing stars' images, seemingly out of whole cloth, it's getting harder to know exactly how we're supposed to regard lesser luminaries of Nicky Katt's or Timothy Olyphant's magnitude. What does it mean to for one these actors to play "edgy" "loose cannons" when (a) their very generation is defined (or not defined) by that slippery concept of "edginess," and (b) exactly how loose their alleged cannons are is debatable. I mean, it's not like anyone's declaring either Olyphant or Katt the new Clint Eastwood -- or even the new Christopher Walken. They just seem to show up in various Gen-X offerings as glowering yet ultimately ineffectual bad-asses. And they're not even all that bad!

Take Timothy Olyphant's showiest role to date, as drug dealer Todd Gaines in Go. [Attention: Spoilers follow.] Sarah Polley's Ronna is so intimidated by him that she...goes straight to his apartment and negotiates a deal to purchase ecstasy in a quantity great enough to sell it. When the deal turns out to be a sting operation and she is forced to flush all the drugs down the toilet, she returns with over-the-counter allergy medication and tries to return it to him and get her money back; he makes a big production of saying that he can't very well fill out a return slip, and that this isn't how drug dealing works, blah blah blah, and is so incensed by her challenge to his drug-conferred authority that he...agrees to do her the favour of taking it back. When he discovers the ruse, he tracks her down to a rave and chases her around the parking lot brandishing a gun until Ronna is run down by a car and thrown into a gully. Seeing her lying there -- and with his firearm still at the ready -- he...assumes that she's already dead and books. Later, he runs into Ronna's friend Claire (Katie Holmes) at a coffee shop. She sinks into his booth and thanks him for "buying [her] breakfast." He fixes her with a penetrating glare and...buys her breakfast. Then they go back to his place and make out on the stairs. Okay, seriously? This guy is about as menacing as Pikachu. This is the villain from whom the poor grocery baggers spend the film fleeing? William Fichtner, as Burke, is ten times as sinister -- and he's playing a cop! Timothy Olyphant does what he can with his haggard skin, sunken eyes, vampiric canines, and intense hair, but he completely fails to fulfill the promise of creepiness that his apperance suggests.

Nicky Katt has much the same problem. Like (future Boiler Room co-star) Giovanni Ribisi, Katt got his first taste of major exposure by guest-starring on Friends; he played a bully who commandeered the Central Perk couch and engaged in a short, very lame fight with Chandler and Ross. He's scarcely stopped working a minute since then, starring in several high-profile movies (like Batman & Robin, A Time to Kill, and One True Thing) and getting cast on a new pilot (David E. Kelley's Boston Public). But he kept returning to the Friends-tested role of minor thug, in movies like The Limey and (in a slight departure) Boiler Room.

And it is in this role that the winner of this match-up has been determined. I was all set to give Nicky Katt my props for playing the tightly-wound if ultimately impotent misogynistic stockbroker Gregg -- a role in which he was even more watchable than as pitiful "enforcer" Stacy in The Limey. But then I saw this still from Boiler Room. And I realized something about the actor I'd previously thought was funny, attractive, and cool:

Nicky Katt is Judd Winick from The Real World San Francisco.

Advantage: Fortunately for Timothy Olyphant, I have an irrational hatred for Judd. Therefore, I cannot award this title to Nicky Katt.