MC Hammer

Stanley Kirk Burrell grew up in Oakland, California, and as an 11-year-old found his way into the Oakland A's stadium parking lot, where he caught the eye of team owner Charlie Finley. Finley hired him as a clubhouse assistant, and the nickname came from Reggie Jackson, who said the kid looked like Hank Aaron. He was "Hammer" before he ever wrote a rap.

In February 1990, "Please Hammer Don't Hurt 'Em" dropped and rewrote the rules. The album spent 21 weeks at No. 1, became the first hip-hop album certified diamond — more than 18 million units sold — and made "U Can't Touch This," built on a sample of Rick James's "Super Freak," a worldwide phenomenon. The single peaked at No. 8 on the Billboard Hot 100 and won Grammys for Best Rap Solo Performance and Best R&B Song — the latter a shared credit with Rick James himself — two of the three Hammer collected that year. Hammer's look — the billowing parachute pants, the relentless full-sprint choreography — became the silhouette of the moment. Mattel made action figures; there were lunchboxes; "Hammerman," a Saturday-morning cartoon he hosted and voiced, hit the air in 1991. His follow-up that year, "Too Legit to Quit," sold over five million copies, its title track climbing to No. 5 on the Hot 100.

But Hammer lived as large as he performed — the enormous entourage, the payroll, the mansion — and by 1996 he filed for bankruptcy, more than $13 million in debt. He became an ordained preacher in the late 1990s and later moved into tech investing. His 1990 moment was perfectly timed: alongside Vanilla Ice's "Ice Ice Baby," it was the year pop-rap conquered the charts — and nobody conquered them harder, or in bigger pants, than Hammer.