5. Michael Waltrip
Races without a win: 138
Not only is Waltrip winless in four years, he's also shameless. Beside pimping himself to any sponsor with a PayPal account, Waltrip bought his spot in 2006's Coca-Cola 600 and used a jet fuel additive in the 2007 Daytona qualifying. We're not sure how Waltrip can shed more dignity this year, but if it'll help him bypass weight restrictions, he'll find a way.

4. Bobby Labonte
Races without a win: 155
OK, this is the year that Petty Enterprises and former Cup champion Bobby Labonte make their big respective comebacks. Along with the U.S. steel industry, disco, the state of Wyoming, and everything else the American public left for dead 30 years ago.

3. Robby Gordon
Races without a win: 162
Never much of a threat to win outside a road course, Gordon once took solace in being the most hated and reckless driver in NASCAR. Now that Kurt Busch has lapped him there, too, Robby's been reduced to carjacking Canadian Busch races. Come on, Robby, put a helmet on somebody!

2. Dave Blaney
Races without a win: 279
Imagine waiting tables at Bennigan's for 11 years and never once selling a patron on the Brownie Bottom Pie. Now you're livin' la vida Blaney who, unlike everyone else on this list, hasn't won a single Cup race his entire career. But he hasn't gone nearly as long without a win as one of racing's biggest names...

1. Kyle Petty
Races without a win: 398
Avoids Victory Lane like it was Compton after dark. Since winning at Dover in 1995, he's only finished in the top five twice, and has led only 87 laps in the last four presidential elections. Is it too late for Richard Petty to have Kyle aborted?