‘Awards Chatter’ Podcast — Bill Simmons (‘Music Box’)

Bill Simmons, this week’s guest on The Hollywood Reporter’s Awards Chatter podcast, is a sportswriter turned media mogul.

Nicknamed “The Sports Guy,” he made his name at ESPN, where he worked from 2001 through 2015 and was behind not only a hugely popular column, but also The B.S. Report podcast, the 30 for 30 documentary series and the sports and pop culture blog Grantland. As The New York Times put it, he “pioneered an intensely personal style of sports writing that draws on frequent references to movies, television sitcoms, music, video games, even his friends and wife (the Sports Gal of course), always with a side dish of mortar-thick sports history and analysis.” Meanwhile, the New York Times Magazine called him “the most prominent sportswriter in America,” Slate described him as “the most influential sportswriter of his generation” and Rolling Stone said of him, “No sportswriter has ever had as much success.”

After leaving ESPN, Simmons founded the sports and pop culture website The Ringer, of which he is CEO, and he established a multiplatform relationship with HBO, for which he executive produced the most-watched sports documentary in the cable network’s history, 2018’s Andre the Giant, and, more recently, executive produced the acclaimed documentary series Music Box, a collection of six documentaries about the music industry which is now in serious contention for a best documentary or nonfiction series Emmy nomination.

Over the course of this episode, the 52-year-old reflected on the roots of his love for sports and pop culture, and how, at the dawn of the Internet, he escaped the restrictions of traditional media by starting a blog before there even was such a term; what led him to ESPN and, once there, to spearhead some of the aforementioned initiatives beyond his column; what was really behind his departure from the Worldwide Leader in Sports, and how his second act has allowed him to revisit and try to improve upon some of the things that he had started during his first, including another podcast in The Bill Simmons Podcast, now coming up on its 1,000th episode and the most-downloaded sports podcast of all time; another sports and pop culture hub in The Ringer; and another docuseries in Music Box.