Shaw was born in South Los Angeles, California, and raised in East Oakland, California during his teenage years. In the early 1980s, Short produced custom raps (called "special requests") for people with his high school friend, Freddy B. In 1983, Too Short released his first album, Don't Stop Rappin', on the local label 75 Girls. This and his next three releases featured raw, simple drum beats using a LinnDrum drum machine in the early 1980s, switching to mostly the TR-808 and TR-909 by the mid-to-late 1980s. In 1986, Too Short and Freddie B. founded the Dangerous Music record label to distribute his music regionally. Dangerous Music later changed names to Short Records, and then Up All Nite Records. With his 1988 release, Life Is...Too Short, he began infusing replayed established funk riffs (rather than samples) with his beats.
Subsequent work including Get in Where You Fit In (1993), and Cocktails (1995), dealt with similar issues. He retired from full-time solo rap with the 1996 release of Gettin' It. He later married Erica Escarcega in 2000. Now they reside in their Taos, New Mexico home with their four children.
Subsequent work was primarily collaborative, including work with Diddy, The Notorious B.I.G., Scarface, UGK, Jay-Z, and Snoop Dogg. One of his noticeable collaborations during this period was on the track "The World Is Filled..." on the classic Notorious B.I.G. album Life After Death; he comes in on the third verse after Diddy & Biggie. Being featured on the album introduced him to a wider audience as well, due to his typical style contrasing greatly with the Mafioso theme of the album. He also appeared on TWDY's hit single "Player's Holiday" from their 1999 debut album Derty Werk as well as the Priority Records compilation Nuthin but a Gangsta Party. After these appearances, he began working on his eleventh album, Can't Stay Away. The album included guest appearances by 8Ball & MJG, Jay-Z, Jermaine Dupri, Sean Combs, E-40, Daz Dillinger, Lil' Jon, Soopafly, Scarface and B-Legit. Too Short relocated to Atlanta in 1994, but he really didn't begin working with a more diverse variety of southern artists until 2000 including Lil Jon. Once 1999's Can't Stay Away was released, Too Short fully came out of retirement and released a number of new albums within the next few years, most of them taking on a crunk or Dirty South type sound, as he had become involved in the Southern Rap scene. However, he didn't totally give up on his trademark funk grooves or sexually explicit style. New albums released 2000-2003 were You Nasty (2000), Chase the Cat (2001), What's My Favorite Word? (2002), and Married to the Game (2003). These albums all charted fairly well, as they all were in the top 71 of the Billboard Hot 200, but they didn't do quite as well as Too Short's earlier 1990s releases as none of them reached the top 10.
In 2004, his earlier 1990 single "The Ghetto" appeared on popular videogame Grand Theft Auto: San Andreas, playing on West Coast hip hop radio station Radio Los Santos.
For his next album, 2006's Blow the Whistle, Too Short now took advantage of the new hyphy rap music that was emerging out of his original home base in Oakland, CA. This saw somewhat of a resurgence for Too Short as it peaked at #14 on the Billboard Hot 200, much better than each of his previous three releases. . However, his subsequent releases, such as 2007's Get Off the Stage, have not been as successful.
On October 7, 2008 Too Short was honored by VH1 at the fifth annual "Hip-Hop Honors" along with Cypress Hill, De La Soul, Slick Rick and Naughty By Nature.
In 2009, Too Short recorded for Daz Dillinger, Lil' Jon, Soopafly, Scarface and B-Legit.