Charles Barkley tried to roast Stephen A. Smith’s outfit on Monday night, but ended up exposing his own strange fashion habit instead. The Manningcast appearance turned into an uncomfortable reveal about the NBA legend’s personal choices.
Charles Barkley Roasts Stephen A. Smith and Reveals His Strange Habit
Charles Barkley Roasts Stephen A. Smith and Reveals His Strange Habit (Image Via Instagram/@br_openice)
Smith sat in Jerry Jones’ suite at AT&T Stadium wearing a bright pink suit. The ESPN personality’s bold fashion statement caught attention as Dallas lost 27-17 to Arizona. Barkley wasted no time attacking Smith’s wardrobe during his Manningcast guest spot.
“I’ll tell you what… I’m not feeling that pink suit. It’s a bit late in the season to be wearing pink,” Barkley said while laughing. Eli Manning had just pointed out that Smith appeared to leave the stadium early in the fourth quarter.
Barkley’s criticism backfired spectacularly when Peyton Manning brought up research about the former player’s personal habits. The Manning brothers decided to address Barkley’s decade-long boycott of underwear during the broadcast.
“Chuck, is it true that you burned all of your underwear almost 20 years ago and haven’t worn any since?” Peyton asked directly. The question forced Barkley toconfirm the bizarre story on live television.
“I burned all my underwear about 30 years ago. … So I’m always going commando for the rest of my life” 😭
We did not have this on our ManningCast bingo card 😅 @OmahaProd pic.twitter.com/1dtiBTTYxw
— SportsCenter (@SportsCenter) November 4, 2025
“Yeah, I realized underwear is not a necessity. It was a big fire, I’m always going commando, for the rest of my life,” Barkleyadmitted. He previously told Jimmy Fallon in 2018 that he’s “been 10 years without underwear” and feels good about the decision.
Eli Manning Gifts Charles Barkley Custom Underwear to End His Commando Ways
The brothers commemorated Barkley’s first appearance on the Manningcast from 2021 with a special gift. Eli produced custom underwear featuring the faces of the Manning brothers printed on them. The gesture aimed to end Barkley’s underwear-free lifestyle.
“I promise you, I’ll put them somewhere prominent in the house,” Barkley said when asked if he’d accept the gift. He stopped short of actually committing to wear them, maintaining his stubborn stance on going commando.
The 11-time NBA All-Star apparently burned his entire underwear collection years ago to create more storage space. His confession about the bonfire raised more eyebrows than Smith’s pink suit ever could.
Many noticed the irony in Smith’s fashion critiques, saying Chuck always roasts others while Barkley’s own unusual style makes him a surprising fashion critic despite his confidence.
Smith earns a massive $140 million contract as one of sports media’s biggest stars. His outfit choices generate discussion whether Barkley approves or not. The pink suit perfectly matched Smith’s bold on-air personality.