In the summer of 1998, two years removed from his comeback run with the Los Angles Lakers, five-time NBA champion Magic Johnson was looking for a new challenge. Sure, he was already a businessman as he’d formed Magic Johnson Enterprises in 1995, but it honestly seemed as if he missed being in front of a crowd and entertaining people.

Enter The Magic Hour.

For those who may not remember, or were perhaps never even aware of, Magic had his very own syndicated late-night talk show back in the day. But while Johnson has succeeded in the vast majority of things he’s attempted in his professional career, The Magic Hour was not one of them, which is why the show didn’t even make it three months.

While ratings were decent in the beginning, even better than The Late Show with David Letterman for a very short period of time, The Magic Hour was panned by critics and the general public alike as Magic never looked comfortable in his new gig. Perhaps the harshest critic of Magic was famed radio talk show host Howard Stern, who repeatedly bashed Johnson in the show’s opening weeks.

As ratings for The Magic Hour plummeted, Johnson attempted to shake things up and get the show back on track by actually inviting Stern to appear on the show, which led to a train wreck of an interview full of bizarre and awkward moments.

Magic Johnson never looked comfortable hosting ‘The Magic Hour’

In theory, The Magic Hour seemed like a decent idea. Magic was always an entertaining personality. But being an entertaining personality doesn’t always translate into being a good talk show host. Just ask Chevy Chase how that worked out.

In the beginning, comedian Craig Shoemaker was Johnson’s sidekick while legendary percussionist Sheila E, who famously collaborated with Prince for years (the two were even engaged for a short time), served as the show’s bandleader. But Shoemaker didn’t last long as he publicly called the show “an absolute nightmare,” and he was replaced by Steve White, another comedian who was already serving in a lesser role on the show. But that didn’t work out either and he was eventually replaced with former In Living Color cast member Tommy Davidson.

Right from the get-go, Magic never looked comfortable. He was very rigid, often mumbled, and his interviewing skills were extremely poor, which certainly wasn’t a good thing when the format was changed to include more time with the guests. Again, as it was something new and the fact that Johnson was already a celebrity in his own right, ratings were solid at the start. But critics jumped all over it and Stern, never one to shy away from bashing anyone, jumped all over Magic as well.

Howard Stern was highly critical of the show

Shortly after The Magic Hour premiered in June 1998, Stern began making it a daily subject on The Howard Stern Show.

Seemingly every morning, Stern would run through the previous night’s episode and just rip it to shreds. He’d mock Johnson’s interviewing skills, his interactions with Shoemaker, his delivery, his lack of chemistry with all those involved, and anything else he could come up with.

Less than a month after the show first aired, ratings were already tanking and the producers of The Magic Hour, one of which was Magic himself, thought it might be beneficial to have Stern on the show. After all, he was the “King of All Media” and his show was listened to by about 20 million people every day. Good idea, right?

Yeah, not so much.

The interview between Magic and Stern was an absolute train wreck

On July 2, 1998, the highly-anticipated interview with Magic and Stern took place and it didn’t take long for things to get uncomfortable. While Johnson tried his absolute best to be the person in control as it was his show, Stern essentially hijacked The Magic Hour from the start and really interviewed Magic more than Magic interviewed him.

As soon as the pair sat down, Stern made comments about Sheila E.’s attire and told her to rip off her top and then went right into telling Magic how to be a better talk show host, starting with Johnson needing to “stop trying to talk like the White man,” and “talk Ebonics all you want.” And if that wasn’t awkward enough, the sentence “I’m Blacker than you are” came next. Seriously, this is all within the first two minutes of them sitting down.

From there, Stern asked Magic about his life before contracting HIV, awkwardly asking Johnson to describe his “booty parties,” later saying, “at least you had fun getting AIDS.” Yes, that actually happened and things just continued to spiral from there.

Stern’s longtime co-host Robin Quivers made an appearance and mentioned how she wasn’t being paid to be there. Playboy Playmate of the Year Karen McDougal made an appearance and talked about a rash she got while modeling. Stern asked Magic if he and his wife, Cookie, practiced safe sex. You know, the usual talk show things. Things ended with Sheila E. and the band giving about an eight-minute performance and she clearly wasn’t happy whatsoever as Stern constantly threw inappropriate comments her way throughout the show.

Stern’s appearance gave The Magic Hour a brief bump in the ratings but, overall, Johnson came off looking even worse than he had before as he was unable to maintain control and looked extremely uncomfortable despite trying to laugh some things off. Two months later, the show was canceled. If you’ve got the 42 minutes to spare, you can check out the entire episode on YouTube.