Michael Jordan and Charles Barkley were two of the best players for much of the 1980s and ’90s. Only teammates on the original Dream Team in 1992, the two were rivals in the NBA. Despite this, they remained friends during their playing days, though their relationship deteriorated in the subsequent years.

A prime example of their friendship can be seen in a joint interview they did on Oprah Winfrey’s talk show in October 2005. The Hall of Famers spent much of the chat trash-talking and making jokes at each other’s expense.

Michael Jordan and Charles Barkley’s friendship

Jordan and Barkley were friends when they made the leap from college basketball to the NBA in the mid-’80s, and they really grew close while spending a lot of time with each other while on the Dream Team.

They were so close to each other that when the players competed in the 1993 NBA Finals when Jordan’s Bulls played Barkley’s Suns, they were still hanging out. In fact, the duo played 48 holes of golf the night before Game 4 of that championship series. Jordan even bought his friendly rival a $20,000 diamond earring.

The guys’ interview on Oprah Winfrey’s show

Winfrey surprised Jordan by telling him she had someone coming out to model one of his outfits, and the “model” was none other than Barkley. The two then spent more than 20 minutes with each other for the interview on the popular talk show.

During the chat, they said they are like brothers, with Jordan just three days older than his contemporary. The two told stories about each other, like Barkley recalling when Jordan “slapped his hand” when he was going to give money to a homeless man. According to Barkley, Jordan’s belief was if the man can ask for money on the street, he can ask a customer for their order at McDonald’s.

Winfrey also relayed quotes from other celebrities — including Will Smith, Magic Johnson, and Larry Bird — about how incredible Jordan is on the court. Winfrey even complimented Jordan and Barkley on their camaraderie, telling them that they “are funny together” and she’d like to see a reality show featuring them. 

Michael Jordan and Charles Barkley trash talk each other

In addition to sharing stories and being complimentary of each other, there was plenty of playful trash-talk to be had on the show. Barkley called Jordan cheap, saying he only spends money on his clothes, then called the Jordan outfit he was wearing “cheap stuff.” 

There was a lot of ribbing of Barkley’s golf game, which is famously bad. They said Jordan refuses to play with Barkley anymore because he’s so bad. When Winfrey said they had video of Barkley taking a shot, Jordan said “No, please. Oh my God.” Jordan continued about Barkley’s golf game, saying “if he makes contact, it’s a good shot.”

The playful jokes even extended to a discussion of Jordan’s then-newfound hobby of riding motorcycles. Barkley talked about not liking motorcycles because of the danger associated with them. He said you won’t be able to get him on a motorcycle, to which Jordan retorted that’s because “the seat’s not big enough” to hold the man who used to be known as “The Round Mound of Rebound.”

When the conversation turned to Jordan wearing a helmet, Barkley said the five-time NBA MVP doesn’t need to wear a helmet because his head is so big. Jordan, the six-time NBA champ, also said that Barkley doesn’t “understand what it takes to be a winner.”