It's a good example of coming up with a unique voice too. Before Simmons, a sports column written from the perspective of a fan was a real anomaly. Then, everyone writing about sports was always trying to be an insider. Simmons deliberately stayed away from the locker room and palling around with players and that's a big reason why his take is so fresh.
Plus, I love that he talks about race in a frank, honest way. Like talking about the complications of the NBA being a league of mostly black players marketing itself to a mostly white audience and a mostly white media. Where else do you hear this discussed in the sports media? Most announcers and journalists pretend to be color blind but then ya listen close and wind up noticing how frequently they talk about guys who "hustle" (i.e. white), guys who are "natural athletes" (i.e. black), etc. Anyway...
A good Simmons starting point: the Sports Guy Glossary which highlights his best stuff. Sample: How to Spot the Guys Who Wield Just A Bit Too Much Power:
The bouncer at any snooty bar ... the deli counter guy who only gives samples to people he deems worthy ... ice skating judges (especially the French ones) ... softball umpires ... the guy at Best Buy who checks receipts before you can leave the store ... sixth-grade gym teachers ... bank tellers ... bartenders in crowded pickup joints ... condo association presidents ... sports radio hosts who hang up on callers when they don't agree ... everyone who works at a video store ... stewardesses on long airplane flights ... movie theater ushers ... the maitre'd at any restaurant in Vegas or Manhattan ... and the hotel worker in charge of the volleyball games at any resort.
Also, his B.S. Report podcast has recently been featuring interesting interviews with funny people (Patton Oswalt, Jeff Ross, Matt Stone, Neal Brennan, etc.) It's worth checking the archives even if ya don't care about the sports stuff.