Comedian Shane Gillis was one of the biggest stars and biggest media winners of the week. He hosted this week’s ESPY Awards and was the most-discussed part of the entire show. He was funny, edgy, pushed the envelope, and took some chances. Shane Gillis is your buddy in the group chat who knows how to take it a little too far, but his likability and delivery are so good that you can’t help but appreciate him.
He did what comedians have done for years, until many were scared off by the cultural overshift to the left in 2020 and 2021. That moment in history scared off many in the entertainment industry. Too many played it a little safer.
But credit to ESPN for letting Gillis tell his jokes, maybe offend some people in the process, but also be the star of the show. This was a huge win for ESPN, which had gone way overboard in recent years as a brand and with many of its top personalities embracing the left-wing politics of the moment. ESPN needed to find a way to sell its male-dominated audience (which leans right) on the idea that it is willing to return to the middle and stop catering to those who aren’t even the target demographic of its content.
ESPN got exactly what it needed here.
Look at these headlines:
FOX News: Shane Gillis stirs controversy with Trump, Bill Belichick jokes during edgy ESPY Awards monologue
Entertainment Weekly: The View hosts react to Shane Gillis’ polarizing ESPY Awards opening monologue: ‘That’s a mistake’
New York Post: Shane Gillis’ fiery ESPYs monologue completely divided the internet
NBC News: Simone Biles wins two ESPY awards as Shane Gillis’ tough monologue grabs attention
Even NBC tried to make it about one of the athletes, but knew they needed Gillis in their headline to stand out.
ESPN was founded on this Wild West, risk-taking, edgy branding nearly 50 years ago (“Those Guys Have All the Fun: Inside the World of ESPN” is well worth your summer reading.). They not only lost that in recent years as they grew into the Worldwide Leader, but they became the antithesis of how they built the brand to begin with. That opened up lanes for Barstool, Outkick, and others to thrive.
Wednesday night was a step in the right direction.
And for radio hosts, program directors, corporate leaders, and frankly, any content creators in 2025, this is what will help you stand out and win.
That doesn’t mean doing something stupid that risks your FCC license. But don’t always play it safe because it’s easy. Take calculated risks. That’s what ESPN did. Sure, The View’s Joy Behar and Whoopi Goldberg were unimpressed and offended on their Thursday program.
But who cares? Liberal women in their 70s and 80s are not the target demographic for the ESPYs. Let them be upset, and let them bring more attention to the product and event you’re trying to promote (of course, The View airs on ABC, which, like ESPN, is a subsidiary of Disney).
And this is one of the many feathers in ESPN’s cap as they try to win over and win back young male sports fans to their original content.
There are so many content options in 2025, that it’s more critical than ever to know your audience and understand how to retain them and win them over. Their choices are too many to take them for granted.
And at least for one night, ESPN did precisely that. And every person with a microphone, every manager and leader, can learn a valuable lesson or receive a timely reminder on this.
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Pete Mundo is a weekly columnist for Barrett Media, and the Vice President of News/Talk for Cumulus Media, while also hosting “Mundo in the Morning” and programming KCMO Talk Radio in Kansas City. Previously, he was a fill-in host nationally on FOX News Radio and CBS Sports Radio, while anchoring for WFAN, WCBS News Radio 880, and Bloomberg Radio. He’s also the owner of the Big 12-focused digital media outlet Heartland College Sports. To interact, find him on X @PeteMundo.
