In a 2011 interview, journalist Jim Miller told NPR: “ESPN doesn’t like stars, actually. I think that they like the idea that the brand is bigger than any one individual.” Miller would know—he co-authored a mammoth oral history of ESPN that came out that year. Up to that point, the network had allowed big personalities like Keith Olbermann, Dan Patrick, and Craig Kilborn to depart for greener pastures. The ESPN brand—and the sports themselves—always trumped the individual talent.
The following year, however, signaled a paradigm shift. In 2012, Stephen A. Smith joined ESPN’s First Take opposite Skip Bayless, and the modern era of the Entertaining Sports Media Personality officially began. Over a decade later, one might argue that ESPN personalities like Stephen A. and recent $85 million signee Pat McAfee actually are bigger than the brand, and are compensated like the athletes they cover.
In the age of the Entertaining Sports Media Personality, the self-proclaimed Worldwide Leader in Sports is just one of many places where fans can consume up-to-the-minute sports commentary, from podcasts to YouTube to social media. And, as in the world of hip-hop media, the voices are coming from everywhere: newspaper vets like Stephen A. and Skip, ex-jocks like Shannon Sharpe, and even rappers like Cam’ron and Mase. The key ingredient? The ability to develop and engage an audience with entertaining opinions about sports.
Note the word “entertaining” in the previous sentence. In putting together this list of personalities, we didn’t focus solely on sports knowledge, although there are insightful pundits throughout; nor did we emphasize access to athletes, even if many on this list are well connected to the superstars they talk about. Instead, we used the subjective yardstick of entertainment value: Who consistently captures the most audience? Whose opinions provoke the most reaction? Who has the most topical range and connects with the widest audience?
With those criteria in mind, we ranked the 25 Most Entertaining Sports Media Personalities Right Now, ranging from young newcomers to longtime industry pillars. The list is based primarily on 2023 performance, but longevity and résumé were also considered. This is our ranking—feel free to embrace debate and argue otherwise.
HONORABLE MENTIONS: Chad “Ochocinco” Johnson, Candace Parker, Matt Barnes & Stephen Jackson, Marshawn Lynch, Manning Brothers, Jeff Teague