The Best Sports Conversationalists

For most sports fans, the games themselves are just a jumping-off point. Sure, there’s the excitement of a Hail Mary or a well-developed attack, but there’s also lots and lots of (often impotent) build-up.

The thing that keeps us engaged over the long-term are the conversations, the arguments, the discussions, that often only use sports as a jumping-off point. Like an emotionally-stunted alcoholic’s book club, an in-depth conversation about sports is often only surfacely about the events themselves.

As such, there’s a large amount of overlap between sports fanaticism, and the arts and politics… novelists obsessed with baseball, presidents attached to basketball teams, Ashton Kutcher standing on football sidelines… the examples are legion.

So, who would be the most interesting people to have in-depth conversations with about the major pro sports? I’m talking about the best conversations, not the conversations that would most blow you away. Obviously, I would love to sit down and watch a basketball game with Michael Jordan. But that would be a simpering fawnfest, not an interesting conversation. So, while athletic experience is nice, it doesn’t really get you many points, unless you’re interesting/intelligent about other subjects as well.

Here’s the current rankings (in order of my like of/knowledge about the sports):


3.) O.J. Simpson – Watching a football game in the visitors room of a prison with O.J.? Guessing it’d be something you’d remember.

2.) Trey Parker and Matt Stone – While they’d be good anyway, hearing these Broncos’ fans take on the Tebow Era jumps it up another level.

1.) John McCain – By far the most interesting politician in recent memory, football would be the perfect canvas to figure out if he’s a political hack, or the guy David Foster Wallace wrote about.

If They Were Still Alive: Hunter S. Thompson

Coming In Last: Chris Berman/Matthew Berry (tie)


3.) Charles Barkley – The rare former athlete who has both a brain and a sense of humor. Warning: a night with Charles Barkley will cost you a minimum of $5,000 in gambling losses.

2.) Jack Nicholson – I know that I’m passing up a more intellectual discussion (Woody Allen) or a more socially conscious conversation (Spike Lee) for stories about doing coke with Wilt Chamberlain and sharing girls with Magic Johnson. I’m good with my decision.

1.) Barack Obama – Regardless of what you think of him politically, he seems like the type of guy that would be interesting as hell to watch a game with.

If They Were Still Alive: David Halberstam

Coming In Last: Tyra Banks


3.) Michael Lewis – Could hold his own in several sports, but the rhythm and length of a baseball game seems most conducive to what I’m guessing would be, at times, a complicated conversation.

2.) Bill James – I would argue there’s a significant downside to baseball’s stats era, but the man started a revolution from out of nowhere (i.e. Kansas). Plus, he knows a bunch about celebrity murders.

1.) Bill Murray – A homer pick, sure, but if you would pass up an opportunity to watch a Cubs game with Bill Murray and an Old Style, we have no common ground.

If They Were Still Alive: J.D. Salinger

Coming In Last: Billy Crystal

European Soccer

3.) Morrissey – Watching a football game with an asexual, vegan music icon? Guessing it’d be something you’d remember.

2.) Ricky Gervais – Best case scenario: it’s like an episode of his podcast, but with Boddington’s. Worst case scenario: it’s like an episode of Extras.

1.) Nick Hornby – Duh.

If They Were Still Alive: Pablo Escobar

Coming In Last: Madonna


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Filed under David Simon Cowell, Sports Has AIDS

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