WATCH: Kenny Rogers Schools Michael Jordan in 1988 Pickup Basketball Game

by Matthew Wilson

Many consider Michael Jordan to be one of the greatest, if not the greatest NBA player. But he’s got nothing on late country singer Kenny Rogers.

The two make an unlikely pairing, much less than on a basketball court. An educated bet would put its money on Jordan ten times-out-of-ten. But they don’t call Kenny Rogers the Gambler for nothing. The country singer more than held his own against the NBA All-Star in this throwback to the 1980s.

Rogers and Jordan isn’t even the strangest match-up. “Space Jam” fans know Jordan once played basketball with the likes of Bugs Bunny and Daffy Duck. The game took place in 1988 for charity as part of the Kenny Rogers Classic Weekend. The three-day festival raised money for charities. It featured musical performances, tennis, golf, fishing, and of course a basketball game for the history books.

During the game, Rogers hit Jordan with a pump fake that shook Jordan. He then made it rain with a jump shot like the best of them could do. And for a moment, Rogers celebrated his small victory. Very few people can say they sank a jump shot on an NBA great. But Jordan didn’t let the country star and his team celebrate for long. Perhaps seeking revenge, he showed them and the crowd why he got paid the big bucks for basketball.

Kenny Rogers Was Also a TV Star

Despite his sick basketball skills, Kenny Rogers will always be known for his music. When he passed earlier this year, the country star left behind over six decades of songs. Rogers was a staple in the industry. But he also had many different interests that he explored over his life including acting.

Yes, Rogers also moonlighted as a TV actor. He played in made for TV movies like “Wild Horses” or “Coward of the County” and made guest spots in other shows. But his biggest accomplishment, TV-wise, was his string of movies based upon his “The Gambler” song.

While Kenny Rogers and Michael Jordan may make for an odd pairing. At least, he didn’t team up with Big Bird.