Bowen Yang and Matt Rogers are officially back in Olympic mode, and they’re kicking off season two of "Two Guys, Five Rings" by diving headfirst into the 2026 Milan–Cortina Winter Olympics. Calling it “the most expansive Winter Olympics ever,” the duo immediately set the tone for a season that’s bigger, bolder, and filled with their signature blend of sports fandom and pop culture chaos. “Let’s just start there — bigger, better, more,” Rogers said. “In terms of the Olympics, it’s like, let’s go for it.”

The hosts are especially excited about taking the podcast on the road, revealing they’ll be attending the opening ceremony in Milan. “They’re actually making the huge mistake of sending us there,” Yang joked. “They’re gonna let us mix and mingle. They’re gonna let us taste the foods.” From Milan’s buzzing social scene and beloved aperitivo culture — described as “nibbles, sips, and more, like, but not too much more” — to Cortina d’Ampezzo’s dramatic alpine setting, the pair paint a vivid picture of the Games’ multiple host cities. “I love this culture,” Yang added. “We’re gonna have the time of our lives.”

As always, pop culture speculation plays a major role, especially when it comes to the opening ceremony. Reflecting on correctly predicting Lady Gaga’s appearance in Paris, Rogers floated the idea of a repeat moment. “It’s crazy that Gaga was out there for the Parisian Olympics when she is famously an Italian girl from New York,” he said, adding, “You’d think she’d be storming the ball for this one.” Yang went even further, throwing Cher into the mix: “I want Cher dressed as Leonardo da Vinci… There’s no reason to believe she shouldn’t come out as Leonardo da Vinci himself.”

Beyond celebrity wish lists, the episode highlights the sheer scope of the Milan–Cortina Games, with competitions spread across cities including Milan, Cortina, Livigno, Bormio, and Verona. From figure skating and hockey to luge, skeleton, ski jumping, and snowboarding, Rogers summed it up best while marveling at the danger of sliding sports: “When I watch skeleton, when I watch luge… I’m like, how do you even practice this?”

As "Two Guys, Five Rings" returns for its Winter Olympics era, Yang promises what fans love most: “We’re exploring human triumph. We’re talking all the locations, stories—and doing more of what we love to do.”

Check out the first episode of Season Two of "Two Guys, Five Rings" on iHeartRadio.

Steve Andrews