On Conan O'Brien, Bill Simmons and ego

Like many of you out there, I watched the final episode of "The Tonight Show With Conan O'Brien" earlier this evening. I thought Conan gave one hell of an exit, particularly in the montage set to the glorious Cheap Trick song "Surrender", his final speech and the final song, "Free Bird", featuring Will Ferrell, Beck, Billy Gibbons of ZZ Top, Ben Harper and the Tonight Show band. You can check that out below:



It was a sad moment for me. I thought SB Nation's Andrew Sharp summarized a lot of it well in this piece; part of the reason many people empathized with Conan was he seemed like such a likeable, modest guy, especially compared to the likes of his predecessor and successor, Jay Leno, whose picture may be found in the dictionary under "Ego". To see a guy like that jerked around and eventually destroyed by a corporate machine isn't a lot of fun.

As mentioned above, the final show was great, though, and it was fun talking about it on Twitter with other writers and sports bloggers. It was interesting to see how much support for Conan there was out there in the tubes of the Internet; of the people I follow, I perhaps saw one or two tweets expressing support for Leno over the past week, and just about everyone else I saw was fervently declaring themselves in favour of Conan. Yet, there was one rather discordant note, and one very relevant to sports; the scathing criticism of Conan ESPN columnist Bill Simmons delivered in this interview with Will Leitch, former Deadspin head honcho and current writer for New York Magazine.

It's not that Simmons is necessarily that far off the mark. Parts of his analysis are right on, such as the bit about not requiring a good lead-in. The vitriol he unleashes, though, such as calling Conan "whiny" and saying his show "sucked" seems a little unnecessary, as does saying that Conan should go back to competing for the "egghead" demographic. On its own, that's not really enough to care about; Simmons is entitled to his opinions, and it's not really that relevant to the sports world what he thinks about late-night television. For me, though, this piece really illustrated the change in Bill Simmons, and why I don't enjoy his writing nearly as much these days.

For those unfamiliar with Simmons, you can catch up on his history at the always-helpful Wikipedia, or you can get the short version right here. Basically, he worked at the Boston Herald for a bit and ran an independent sports website; he then jumped to ESPN, became a writer for The Jimmy Kimmel Show for a couple years, wrote two books (Now I Can Die In Peace, a 2005 book about the Red Sox's 2004 World Series victory, and last year's The Book of Basketball), took up podcasting in addition to his columns and helped put together ESPN's excellent 30 for 30 documentary series.

When he first started, Simmons was particularly noteworthy for writing from a fan's perspective. He became one of the first bloggers to achieve real mainstream success, and inspired many others in the process. Over time, that changed, though, and now he's largely disassociated himself from the blogosphere, as Andy Hutchins points out in this post. Why and how has Simmons changed, and how does this relate to late-night television?

I think the change in Simmons is perhaps most prominently displayed in his books (both of which are excellent). Now I Can Die In Peace was a deeply personal story about Simmons' history with the Red Sox and their litany of soul-crushing defeats. It was something readers, writers and sports fans could empathize with. By contrast, The Book Of Basketball was a much more ambitious and egotistical project; it was basically Simmons' attempt to categorize all aspects of the NBA's history and rank its players and teams. There were still plenty of personal anecdotes and fan moments, but it was much more declarative. Instead of telling us about why he loved particular players or teams, Simmons told us why player X was definitively better than player Y. That's where I think he went wrong.

As long-time readers of this site will know, my mission statement is to go beyond the black and white analysis that pervades our sporting culture and into the shades of grey. I'm more interested in hearing subtle, nuanced takes on a story from both sides than over-the-top diatribes against one side. I don't think Simmons was ever really in that camp, as even his earlier days saw everything through the light of intense fandom. The key distinction was that he used to see his thoughts as AN opinion, rather than THE opinion, though. Then he got famous, people started relying on his opinion, and he lost track of all perspective and became egotistical. His columns and podcasts aren't discussions of issues in sports these days, they're revelations of Bill Almighty's opinions on sports. That same kind of attitude came through in his discussion of the late-night situation, but perhaps even more explicitly; the whole article read as Bill's decrees on what happened and what should come from it.

That's not to say that no one should ever express opinions on sports. One of the things I love about the blogosphere is the democratization it provides; everyone now has an outlet to express their opinions, and many of those people never would have been able to crack the ivory towers occupied by the mainstream sports media. There's nothing necessarily wrong with strong opinions either, or listing and ranking players. I think the key problem is when people go from thinking their opinion is a point of view to thinking it's the only reasonable point of view.

In my mind, that's what we've seen with Simmons. That's why he doesn't actively read many blogs these days, or engage with much of the sports blogging community; he has no need for their feedback. Sure, he'll run occasional e-mails from readers in a mailbag, but he rarely prints those that are overly critical of him. That's why his Twitter account reads like far more of a collection of his one-liners than an actual way for him to interact with anyone. In a lot of ways, he's the Jay Leno of the sports world; he doesn't care what anyone thinks of him and he isn't particularly worried about providing things that will engage his fans, as he still can draw viewers and he still has friends in high places.

I'm not out to vilify Simmons, though. I enjoyed both his books and I still read his columns regularly, even if I don't like them anywhere as much as I used to. What I'm more concerned with is what happens if other bloggers fall into the Simmons trap and starts to think,in the famous words of Ron Burgundy, that they're kind of a big deal. It's an easy way to follow, and once you start down that dark path, forever will it dominate your destiny. However, it's important to remember that a large part of the success of the blogosphere has come from bloggers being open to comments, dialogue, feedback and other opinions in a way that traditional media outlets never were for decades. If we keep that in mind, hopefully the future of sports blogs will be much more like the fun, self-deprecating Conan than the egotistical Leno or Simmons.