The 50 Coolest Football Players in NFL History

Sports media loves nothing more than debating the NFL’s greatest players, but to hell with that noise, we’re here to talk about what really counts: the NFL’s coolest players ever. These are the players who you would love to grab a beer with – or something stronger – or who set the standard in style, grace or just plain old badassery. After all, there are a lot of different kinds of cool, and in the wild history of the NFL, just about all of those kinds of cool were well represented, especially by these, the 50 coolest football players in NFL history.

50. Bob St. Clair

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The 6’9” St. Clair is one of the most underrated of all NFL greats, as he kicked ass during the ‘50s with the 49ers. Now that we got the bio out of the way, let’s get to what really counts: Bob St. Clair ate raw meat. I don’t mean just once, I mean his whole life he ate raw meat like a goddamn savage. And then after he retired, he decided to really live the dream and opened his own bar. Cold beer and raw steaks. This was indeed the greatest generation.

49. Ronnie Lott

Ronnie Lott was a total badass. I mean, how else do you explain a guy who had his broken finger fucking amputated so he wouldn’t have to miss a game? Insane, yes, but a cool sort of insane.

48. Andre Rison

Andre Rison was so cool that he managed to not only snag one of the members of TLC, he drove her so wild that she burned down his goddamn house. Sure, that probably sucked, but on a deeper, spiritual level, that is baller as hell.

47. Thomas Henderson

He’s better known as “Hollywood” Henderson, and if you’re walking around with that kind of nickname, you better be able to back that shit up. And Hollywood Henderson tried his damn best as he managed to walk the line between badass football player and badass party god better than just about anyone. It all came crashing down eventually, but it’s always cooler to burn out than to just fade away.

46. Randy Moss

Look, Randy Moss is kind of a jackass, but let’s not front, he’s also pretty damn cool. I mean when a reporter asks you how you pay your fines and you instantly respond with “Straight cash, homey,” you are winning the game.

45. Chuck Bednarik

Chuck Bednarik was cool because he was the last NFL player to go two ways back in the day. No, I don’t mean he was giving handjobs to teammates while fingerblasting the cheerleaders at the same time – although, let’s be honest, that would be cool as hell in its own Roman orgy type way – I mean he was the last dude to play both offense and defense, kicking ass the whole game without ever taking a break. Now that’s a goddamn man.

44. Deion Sanders

“Neon” Deion was a lot like Randy Moss in that he was kind of a jackass, but you can’t deny the immense amount of swag he brought to the game. I mean, come on, the dude would high-step down the field on touchdown returns. This was a dude who was cool and he knew it.

43. Donald Gibb

Donald Gibb was barely in the NFL – he hung around the Chargers for a while – but who cares? He was Ogre in Revenge of the Nerds and was Jean-Claude Van Damme’s bro in Bloodsport. All other arguments are invalid.

42. Brian Bosworth

The Boz was ridiculous as hell. No one is arguing that, but back in the day, he was actually cool for a minute. He was the poster boy for Barry Switzer’s Oklahoma teams of the late 80s that became some of the most infamous ever, and he rode off to the NFL in a haze of drug suspensions and wild accusations. He warred with the NCAA, pissed off half the country and became a symbol of renegade cool in the midst of the Reagan era. So what if he was exposed as wildly overrated once he hit the NFL? Maybe the Boz was just too cool for the NFL.

41. Dick Lane

Look, anytime you’re better known as Dick “Night Train” Lane, you are doing good things. That is one of the all-time great, cool names. But Night Train actually earned that shit as one of the best NFL defensive backs ever, and off the field he romanced famous jazz singer Dinah Washington. You don’t do that unless you have some serious game.