Charles Barkley has never held back, whether it’s courtside commentary or cracking jokes live on air. But his charm isn’t just in bold opinions; it’s also in the chaos he brings. Like during the 1992 Olympics, when he elbowed Angola’s Herlander Coimbra and called it a playground scuffle. No punishment followed, and oddly enough, fans still loved him. If that wasn’t enough, he once roasted Shaq’s spelling live for $10,000, and starred in T-Mobile’s “Fave Five” commercials, battling it out for spots on each other’s contact lists. But if he loves something more than his love for pranks, it’s probably his love for food!

All throughout his NBA fame, Barkley was always pulling stunts. There’s the All-Star race where he beat 67-year-old ref Dick Bavetta and ended it with a hug. Justified why he is in the #2 in all-time Technical Fouls. But these don’t bother Chuck much. While covering the Knicks-Pacers series, Barkley lit up the studio talking about New York street food. “Tomorrow, I’m getting the street meat,” he said. Minutes later, producers surprised him with some right on set. Did he hesitate?

Not for a second. “I don’t even care what kind of meat it is, dog, rat, cat,” he said between bites. He once said, “People say I eat a lot. I really don’t. More or less, I just eat all the time.” And his love for Krispy Kreme is not a secret. That’s exactly why Dave Portnoy thinks Barkley deserves the VIP treatment. The Barstool Sports founder is gearing up for his One Bite Pizza Festival this September in New York. With over 30 iconic pizza spots and even a dessert village, it’s a food-lover’s dream. So, who’s Portnoy hoping shows up?

“I’m always like a Charles Barkley fan,” he told TMZ. “He’s a little heavy. I assume he likes pizza. You don’t weigh like that and not like pizza. So if he wants to come, he’s got a free VIP ticket waiting for him.” Now, if something ought to get Chuck’s attention, this would be it! And if Barkley does show up, it might feel like a full-circle moment. Back at Auburn, he and Bo Jackson had their own food hustle going on. Barkley previously shared how they’d order pizza to the dorm, and while the delivery guy was at the door, other players would sneak into the car and swipe extra pies. “We probably stole more pizzas than we paid for,” he laughed.

It became a ritual, one they pulled off more than once. “We’d order like three or four pizzas, but we’d always steal like two or three.” Auburn may have been known for football, but it also had a dorm full of hungry legends with fast hands. Now, decades later, Barkley’s pizza days are finally going legit, with a side of VIP.

Why Charles Barkley might not laugh off Dave Portnoy’s comment about his weight

While Dave Portnoy’s playful “he’s a little heavy” comment was meant to get laughs, it might not land well with Charles Barkley. Behind the jokes and pizza invites is a man who’s been working seriously to shed pounds, not just for looks, but for health. Barkley isn’t just winging it either. He’s dropped 50 pounds recently and partnered with Ro, a telehealth company, to help others follow the same path.

“I know GLP-1s work, I’ve seen it for myself,” Barkley said. His approach hasn’t been just about treatment; it’s been about tackling the access problem that keeps regular folks from getting the care they need. In his words, “The hard part (for me) was getting the medication when I needed it. That’s where Ro comes in.” Barkley made it clear this isn’t a celebrity vanity project. It’s about showing that anyone, celebrity or not, deserves support in taking charge of their health.

What makes Barkley’s latest chapter more powerful is his vulnerability. He knows what it’s like to fall off track and start over. That’s why when he said, “Let’s go to work!” he meant it as a message for anyone who’s been in the same fight. He’s even turned his journey into something fun, starring in Ro commercials that blend his humor with his mission. “Working on these Ro commercials was a blast,” Barkley said. “I got to be myself, joke around a little, and most importantly, talk about something that can really help people.”

So while Dave’s pizza party sounds tempting, Barkley may be thinking long term. He’s not just the “Round Mound” anymore; he’s a man on a mission.