By age 17, Todd Shaw already knew the secret to success in the rap game. Too $hort’s first album, released on cassette in 1983, was called Don’t Stop Rappin’—and despite a brief (staged!) flirtation with retirement in the early 90s, the Bay Area legend has certainly has lived up to that motto. It’s 2012 now, and Too $hort’s 19th album, No Trespassing, is due out in a week.

$hort’s formula—and indeed, many of his dirty rhymes and thick-ass beats—have hardly changed since the days when Felix Mitchell was the king of Oakland. Too $hort will turn 46 this year, but you still wouldn’t want to listen to his music around your mother—or, for that matter, underage kids. In a recent video produced by XXL, $hort offered “fatherly advice” to young boys looking to “turn girls out.” It was not a good look, and after the video led to a firestorm of controversy and the suspension of staffers who posted the clip, $hort offered up a rare but apparently heartfelt apology.

Short Dawg’s foul mouth and nasty sense of humor are legendary. But believe it or not, they are tempered by a community-mindedness that one might not expect from the man who loved the songs “Blowjob Betty” and “Invasion of the Flat Booty Bitches” so much he recorded them both twice. But one of his first songs, “Girl (That’s Yo Life)” is a cautionary tale about crack cocaine, which was tearing Oakland apart at the time.

His latest video, “What The Fuck,” features Occupy protesters, who have been tearing up the Town in their own way. This delicate balance between dirty raps and actually giving a damn has helped Short achieve longevity that few rappers will ever enjoy. What better time, then, to have Too $hort Break Down The 25 Most Essential Songs in his massive catalogue? So click through and read up, because life is too short.

As told to Willy Staley (@bushwickwill)

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