So, if his writing was always shitty, and fame and access actually improved his skill-set, then why don’t you like Simmons as much as you used to? What changed?
You did. You are not 19 anymore. You matured, read other, better writers, and eventually discovered the difference between an analogy and a reference, between affectation and personality, between pointless maundering and having something to say. You grew to prefer coherence over in-group signaling. You figured out that writing that claps you on the back and congratulates you for being careless and white and male and steeped in mainstream pop culture is the precise opposite of subversive. You lost your taste for Bill Simmons, whose writing is bad. You grew up. Good for you! Growing up is cool.
Yeah, pretty much. For my case the sentence should read, "You are not 36 anymore." When I discovered Bill Simmons, it must've been 2000 or so, I was charmed. It didn't take too much reading in his ESPN archive to catch on to (and, I suppose, be flattered that I caught on to) his inside jokes, the private language and set of pop-culture references.
What took a little longer to figure out: Simmons and his group of college buds, who featured in his columns, reminded me of my group of college buds. That had a powerful nostalgic pull on me. At the time, I was in a doldrums related to being the parent of small kids, a life stage that can make one feel boring and prematurely old. I was missing my male circle from college days. We too had our private vocabulary, our favorite movies and pop songs and other clever references. I thought this dense groupthink made us distinctive and rare.
It does NOT make us distinctive or rare, I've come to understand, after yet a little more time. Five million frat bros can't be wrong, from a mass marketing perspective, but they can't all be special. That has been a little painful to accept, along with other intimations that my college experience was not as magical as I once felt it was.
Parallel to that sad acceptance, I've found it harder to slog through Simmons's prose. To his credit, Grantland publishes some writers I really admire (Charlie Pierce, Bryan Curtis, and Brian Phillips are the principal names) who make Simmons's own writing look pedestrian by comparison.
(It also publishes some folks who read like obsequious Simmons acolytes. That's understandable; he certainly hit on a winning formula, for anyone able to follow it. Deadspin itself could be said to take the Simmons M.O. and improve it.)
As this piece hints, Simmons has turned out to be pretty good as a publisher, producer, and all-round businessperson. At ESPN he leveraged his pageviews into the 30 for 30 videos and Grantland, and both those things have had some good moments. I hope Bill surfaces somewhere that understands him and gives him latitude to sponsor more good young writers and filmmakers. He has an aptitude for that. But his writing... I'm over it.