Charles Barkley -
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Charles Barkley

Charles Barkley is one of the most entertaining people in sports media and honestly he was one of the most entertaining people in sports before that too. The guy played 16 seasons in the NBA, won the MVP in 1993, made the All-Star team eleven times, and did it all while being listed at 6'6" in a league full of seven-footers.

He played for the 76ers, the Suns, and the Rockets. In Phoenix he had his best year, winning MVP and dragging the Suns to the Finals in '93 where they lost to Jordan's Bulls. He never got a ring, which he'll be the first to tell you about. But the Hall of Fame? That happened in 2006. The talent and the numbers were never in question.

After retiring, Barkley became a studio analyst on TNT's Inside the NBA and basically became more famous than he was as a player. He says whatever he wants, he's hilarious, and he doesn't care who disagrees with him. It's made the show must-watch television for basketball fans.

On Shark Tank he shows up as a guest and brings a totally different energy than the typical business-world sharks. He's not going to grill you on your EBITDA margins. But he does understand branding, he understands what it takes to stay relevant for decades, and he's been involved in enough business deals to know what a good opportunity looks like.

Career highlights: