Rearview mirror: The coolest, and un-coolest, athletes of the 2000’s

Top: Coolest.  Bottom: Least coolest. (Like I have to tell you) Note Reggie in bottom left holding hands with a referee

Another set of lists as part of our friends at Trumbull Island’s Year/Decade-ending Top 10 list hysteria. Here are the Top 10 coolest athletes of the decade, and the Top 10 least coolest athletes. I’m sure I’m missing some, but I think it’s a pretty good primer. I think you’ll see Nas is generally a good barometer here. Feel free to let me know some other guys I missed.

Top 10 Coolest Athletes

10. Tom Brady – Plenty of haters out there, but he’s the man. Who wouldn’t want his life? I’m a Dolphins fan, and I’m still big on this guy. Won three Super Bowls and married this. To top it all off, he hit the links with Vinnie Chase on Entourage.

9. Chris Webber/Jason Williams – Early ‘00’s Kings were the most fun team in sports. Every kid on the playground wanted to play like White Chocolate. And Webber produced Nas’ ‘Blunt Ashes’ and ‘Surviving the Times.’

8. Arturo Gatti – if you’ve ever been to one of his fights, you know Gatti’s the man. Four time Ring Magazine “Fight of the Year” winner. Rest in peace, champ.

7. Antoine Walker – Here for one reason – infamous answer to question about why he shoots so many threes: “Because they don’t have fours.”

6. Ichiro – Sweet player. But besides that, another super-quotable athlete. He unleashed this gem in August:

Chicks who dig home runs aren’t the ones who appeal to me. I think there’s sexiness in infield hits because they require technique. I’d rather impress the chicks with my technique than with my brute strength. Then, every now and then, just to show I can do that, too, I might flirt a little by hitting one out.

5. Steve Nash – I remember back in ‘05, the Mavs decided to play him to pass. And he scored 48 in one game, and then 39 to eliminate them. Gangsta. Lives in NY in offseason, rides skateboard to the gym. And he’s hilarious.

4. Mike Piazza – Won first game after 9/11. Beasties claimed to be “Clutch like Piazza.” Married a Playboy Playmate – which was actually somehow a step down after previously dating Playmate of the Millennium. Outside sports, he has appeared on “Married … With Children,” among other ventures.

3. Charles Oakley – Said stuff like, “If it ain’t broke, don’t break it.” Used to wear sweet purple suits. Probably still does. Once was beaten to the lane by Bo Outlaw and responded by breaking his nose. Randomly worked out with some kid at U of Buffalo, ended up buying him dinner. Does a cooking show called “Oakley Cafe.” It’s the greatest cooking show in history.

2. Barry Bonds – The greatest hitter ever. The game looked the other way in his heyday, then turned on him, and he didn’t really care. Unapologetically broke Hank Aaron’s record (on the eve of my birthday). Iconic Kanye West song seals the deal.

1. LeBron James – Was The Man at 18. Turned 25 today, scored 48 to celebrate. Friends with Jay-Z, which all of us would like to be. Before all is said and done, could be the G.O.A.T. (Apologies to Mike, but when LeBron starts winning rings, he may not stop)


Top 10 Least Coolest Athletes

10. David Eckstein – Do you really have to sprint to first base after drawing a walk? Really?

9. Derek Jeter – I respect his work ethic, and like Brady, his life is awesome. But he’s just so lame, so safe, so sanitized. I’m sick of hearing about him being “the new DiMaggio.” The next thing he has in common with The Great DiMaggio will be the first thing.

8. Brett Favre – He’s just having fun out there. He’s such a gunslinger. Like a kid in a playground.

7. Lennox Lewis — “Beat” Vitali Klitschko when they stopped their fight for Klitschko’s cut. Vitali was up on every scorecard. Lennox claimed he had no more challenges and bolted, effectively killing the heavyweight division. He now bores us all with banal commentary.

6. Michael Phelps/Tiger Woods – Both traded off their squeaky clean image, then proved to be complete hypocrites. Sick of hearing how much Phelps eats. Hey Phelps, try taking on Kobayashi. As for Tiger, cheated on this. Nas labeled him an Uncle Tom in a great song. He plays golf.

5. Tyler Hansbrough – A master of horrible flops and uncalled travels. Stayed at UNC until he was 23 1/2 to win a national title. I once got in an argument with him about some regulation when he was in high school. I was correct. This actually happened.

4. The Spurs – All of them. Horry gets a slight pass for Nas’ shout-out. The team assumes Duncan’s vibe, and he’s boring as hell and whines like there’s no tomorrow, though I have to admit his sneakers are sensational. Popovich tanked a season to get Duncan and has coasted on that ever since. Ginobili flops more than a Jason Biggs movie. (For that matter, so does Horry) Parker and Eva: horrible. Plus, he’s French.

3. Reggie Miller – Speaking of flopping, Miller looked like a hooked fish on the deck of a boat. A strong wind would blow him over, and he’d get a whistle. Nobody ever tuned into a game saying, “Man, I can’t wait to watch Reggie hurl himself to the ground tonight!”

2. Isiah Thomas – Obviously, he’s not an athlete anymore, but we’ll count him on the grounds that he attempted to ruin one of the most historic franchises in sports history. Imparted for the Knicks horrible and high-priced players like Jerome James and Eddy Curry. Most notably, harassed women. I don’t endorse that. Now coaching Florida International. They’re 4-11.

1. Alex Rodriguez – Is there anyone who likes this guy for anything other than irony? A complete phony, and a fitting choice for the lamest sports figure of the decade.



  1. What's up Jeter hater! Cheater and poster boy for steroid era Bonds cool, but stand up, classy champion Jeter uncool? Why don't you check yoself and provide a link with Jeter's GF Minka Kelly.. Simply appauling! I like the rest of it tho 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *