NBA legend Michael Jordan has battled numerous opponents throughout his brilliant career. Elite basketball superstars, monsters from space, and even celebrities, Jordan has battled them all! Back in 1987, the six-time NBA champion made a highly publicized feature on a popular show where he squared up against Charlie Sheen. Along with his father, Charlie Sheen battled the then 24-year-old MJ with the whole world watching.

Jordan and the Sheens took part in a friendly basketball competition in a crowded gym. This was a part of the War of the Stars TV show which featured celebrities squaring off against one another. With various handicaps, Jordan still dominated. However, his overconfidence cost him as he embarrassed himself against the Sheens.

Michael Jordan was once defeated by actor Charlie Sheen and his father

Needless to say, Michael Jordan hates losing. The former MVP has been to six NBA Finals and won them all! Additionally, he has six Final MVP awards to his name. Jordan is built for the big moments.

However, he faltered when he faced Charlie Sheen and the actor’s father in a friendly matchup. They played three games which involved a free throw competition, a game of HORSE, and a 2v1 matchup. To make it easier for the Sheens, the producers of the show had implemented handicaps in the game.

For the first game, Jordan had to shoot free throws with his eyes closed. Prior to starting the exhibition, the Chicago Bulls legend seemed pretty confident and asserted that he shot free throws with his eyes closed all the time.

Little did he know, he was in for a surprise. Both teams had to shoot 20 free throws and Jordan made 11 of them. Interestingly, the Sheen team beat Jordan in this matchup as they got 12 free throws!

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Charlie Sheen’s brilliant free throws sent the crowd into a frenzy with the commentators also on their feet. The commentator exclaimed, “There’s number 6, he’s already tied Michael’s score! Perfect! Wow, that’s seven in a row.”

Although Jordan lost the first match, he made up for it in the second. With the third matchup starting, everyone expected Jordan to win, however, he was in for another surprise.

The Sheens humbled MJ in front of the crowd

The final matchup between His Airness and the Sheens was a 2v1 battle to 10 points. The catch was, Jordan had only one shot at the basket and the Sheens started their score at 5.

Despite being one of the best players in the world, the handicaps and the Sheens made Jordan sweat it out. He took the game to the wire and eventually lost, which left the basketball world bamboozled.

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