Athletes as Artists: The Cultural Overlap Between Sports and Entertainment Icons

Twenty years ago, a great athlete had a jersey number and maybe a shoe deal. Today the best ones have a shoe deal, a clothing line, a Spotify page, and a seat at the Met Gala. The line between “athlete” and “entertainer” has been fading for a while, and looking at how it happened shows just how far the overlap is.

From the locker room to the runway

Fashion is one of the clearest places to see athletes in culture. For example, Serena Williams launched her own label, S by Serena, and presented it at New York Fashion Week in September 2019, stepping fully into a role as a designer rather than just a face for someone else’s brand.

The Met Gala has also become the yearly proof of how normal this crossover has become. For its 2025 edition, themed around Black style in menswear, LeBron James and Formula 1 driver Lewis Hamilton were named honorary chairs alongside Colman Domingo and Pharrell Williams. The guest list also included Simone Biles, Sha’Carri Richardson, and Angel Reese.

A room once reserved for actors and musicians now reliably includes some of the biggest names in sports.

From the court to the studio

Music has its own long history of athletes crossing over, and it didn’t start recently. Shaquille O’Neal’s 1993 debut album, “Shaq Diesel,” went platinum, with two of its singles certified gold by the RIAA. At that time, a star center putting out a rap record was still a novelty rather than an expected side hustle.

That side hustle is now a full career for some current players. Portland guard Damian Lillard records and performs under the name Dame D.O.L.L.A., releasing multiple albums including “Confirmed” and “Big D.O.L.L.A.” while still playing in the NBA.

And this isn’t a hobby spruced up for headlines, but an actual second act happening in parallel with his day job. As athletes build these second careers, the digital entertainment market gives them even more ways to reach audiences beyond the game.

From the arena to the boardroom

None of this crossover happens without the money to support it, and the brand deals behind today’s athletes are built on a different scale than they used to be. LeBron James signed a lifetime endorsement deal with Nike in December 2015, a deal his own business partner has since described as worth roughly a billion dollars over his lifetime. A contract like this turns an athlete into a long-term brand asset rather than a seasonal sponsorship, which is what lets someone like James move as easily into film and business ventures as he does onto the court.

From the sideline to the sportsbook

Sports betting has become part of this same commercial world, following a similar arc. The turning point was 2018, when the U.S. Supreme Court struck down the federal law that had blocked most states from legalizing sports betting, opening the door for states to write their own rules.

Leagues that once kept betting at arm’s length moved quickly once that changed. In 2021, the NFL named DraftKings, Caesars, and FanDuel as its official sports betting partners in a set of deals reportedly worth just under a billion dollars combined.

Athletes themselves followed. Hockey legend Wayne Gretzky signed on as a brand ambassador for BetMGM, later appearing alongside Tom Brady in a Super Bowl commercial for the brand. As a result, sports events and athletes have gotten better financing, and fans found ways to be more involved in the matches with options like live betting at Sportbet or long-term parlays.

The NBA’s 2023 collective bargaining agreement went further, allowing active players to endorse sportsbooks and fantasy sports companies and hold small passive investments in betting companies tied to the league. Kevin Durant and Trae Young were among the first to use that new rule, investing in Underdog Fantasy alongside Mavericks owner Mark Cuban.

One ecosystem now

Fashion lines, rap albums, billion-dollar shoe deals, and sportsbook ambassadorships all look like separate stories, but they’re really the same one told a few different ways. Modern athletes build a media presence that looks a lot like a musician’s or an actor’s, right alongside the actual competing, and the entire industry around sports, from apparel to betting, has restructured itself to keep up with that shift.