Too $hort was among the first West Coast rap stars, recording three albums on his own before he made his major-label debut in 1988 with the RIAA-certified gold Born to Mack. Anticipating much of the later gangsta phenomenon, he restricted his lyrical themes to explicit tales of sexual prowess and street life, with the occasional social message track to mix things up. Likely the only rapper to have recorded with 2Pac, the Notorious B.I.G., and Jay-Z -- all superstars indebted to his work -- he has remained an inspiration for his vulgar verses and sparse instrumentals, remaining an iconic presence in the hip-hop landscape through the ensuing decades with projects like 2020's E-40 collaboration Ain't Gone Do It/Terms and Conditions.

Born Todd Shaw on April 28, 1966, Too $hort grew up in South Central Los Angeles. Soon after his family moved to Oakland in the early '80s, he began selling tapes out of the back of his car. Signed to the local label 75 Girls, in 1985 he released his first proper album, Don't Stop Rappin'. Two albums followed in the next two years, after which Too $hort formed his own Dangerous Music label with friend Freddy B. He released Born to Mack in 1987, and sold more than 50,000 copies just by riding around the region. New York's Jive Records picked up on the buzz from across the country, and re-released the album one year later. With virtually no radio airplay, Born to Mack went gold and its follow-up, Life Is...Too Short, achieved platinum sales by 1989.

Immense underground success and nationwide distribution primed Too $hort for radio airplay. "The Ghetto," from 1990's $hort Dog's in the House, made number 12 on the Billboard R&B/hip-hop chart and enjoyed a brief stay just outside the Top 40 of the Hot 100. The roll continued with 1992's Shorty the Pimp and 1993's Get in Where You Fit In, both of which went platinum. By the time of 1995's Cocktails, however, Too $hort began to be drowned out by a glut of similar-sounding West Coasters, and though Gettin' It (Album Number Ten) eventually became his sixth platinum album, by late 1996 he decided to retire. Three years later, however, he returned with Can't Stay Away, which debuted in the Top Ten and went gold. Back for the long term, Too $hort released four albums during the next four years, then in 2006 scored one of his biggest hits with the Lil Jon-produced title track for Blow the Whistle. After Get Off the Stage was released in 2007, Too $hort returned to independence. During the 2010s, he issued the albums Still Blowin', No Trespassing, the guest-loaded Hella Disrespectful: Bay Area Mixtape, The Sex Tape Playlist, and The Pimp Tape, on his Dangerous Music label. He rounded out the decade in 2019 with the release of his 21st studio album, The Vault. The next year he returned with fellow Bay Area legend E-40 on the collaborative mixtape Ain't Gone Do It/Terms and Conditions. In addition to the two headliners, the tape included guest spots from Larry June, Freddie Gibbs, G-Eazy, Guapdad 4000, and many others. ~ John Bush & Fred Thomas, Rovi