Bill Simmons is known for his hot takes and historical references on sports like basketball and football, but he’s also had his pulse on pop culture.
The Ringer, the media company he founded that was sold to Spotify in Feb. 2022, has always covered a mix of sports and culture. Same for Grantland, the ESPN-backed website Simmons founded in 2011 which closed in 2015.
And so on Simmons podcast, “The Bill Simmons Show,” he tends to sprinkle pop culture topics, and on the Wednesday, Feb. 28 episode of the show, Simmons brought on pop culture writer Chuck Klosterman and asked him what he thought about the rise of Taylor Swift.
Simmons asked particularly whether he thought that Taylor Swift is the most famous person in the world since Michael Jackson.
“She’s more famous than Michael Jackson,” Klosterman responded.
He said he’s talked about this at length with many people, but instead compared Swift to The Beatles.
“Could the Beatles have sold out six nights at Shea Stadium the way she sold on all those nights at SoFi [Stadium?],” Klosterman posited.
He said that perhaps The Beatles could’ve matched Swift during their time, though prices for concerts were significantly cheaper in the 1960s when they were famous. But Klosterman said that one of the separators of Swift even from The Beatles is her ability to encapsulate the hearts of all ages.
“The key seems to be that she has almost completely saturated both the U.S. market, the consumers, the teenagers, but also like their moms and their parents,” Klosterman said.
Simmons, who didn’t definitively say whether he thinks Swift has surpassed Jackson or The Beatles, said that he thinks one of the separators of Swift has been her longevity.
“It’s so hard to stay as relevant as she stayed,” Simmons said. “My daughter is 18 and a half and there was just making music her entire life so that and she’s more famous now than at any other point in my daughter’s life.”
He then argued that many of Swift’s notable actions, whether with her music or outside of it, have never really put her in a bad light.
“I don’t know whether this was intentional or semi intentional or how it played out — but there’s been a couple points in her life when she did things that just resonated with people,” Simmons said.
He cited how Swift took ownership of her music by redoing her old albums, as well as her controversies with Kanye West, which have all come around to only grow her brand.
Simmons also said that some of Swift’s moves that have been out of the ordinary, like dating Travis Kelce, have seemed to work.
“Every time she’s zagged, it’s been the right move, even like this Travis Kelce relationship,” Simmons said. “I don’t know if it was intentional, semi-intentional, not intentional, but her dating a famous NFL star was like just a fantastic career move … She seems like a f—ing genius at how to have a career.”
Swift’s success has also been a topic of conversation of the right. Many have put out conspiracy theories that her success with the NFL could help boost the campaign of President Joe Biden. Politics aside, Simmons said just the fact that Swift could have this type of impact is another major separator between her success and other previous stars.
“Trump is literally afraid of forgetting about the election in some way and that she could swing it,” Simmons said. What other artists or athletes would we have ever said that about over the last 40 years that somebody a celebrity could come in and actually nudge an election?” Simmons said.
It’s unlikely that there will be a specific barometer to measure whether Swift has matched or surpassed the success of other artists — especially considering how social media and inflation have affected the world. But Simmons having this conversation with Klosterman, and making the points that they made, shows that Swift has clearly reached historic levels of popularity.
