Born Antoine Roundtree, Skee-Lo emerged from the Los Angeles hip-hop scene in the mid-1990s with a playful, self-deprecating style that offered a refreshing counterpoint to the harder-edged West Coast gangsta rap dominating the era. Raised in the Los Angeles / Riverside area of Southern California, he developed a distinctly relatable everyman persona — rapping about being short, wishing for more, and dreaming of a better life — that turned him into one of the most instantly likable voices of '90s hip-hop.

His breakthrough came with his debut studio album I Wish (1995), which went gold in the U.S. on the strength of its signature title track. "I Wish" — anchored by a sample of Bernard "Pretty" Purdie's "I Wonder Why" and Skee-Lo's now-iconic opening line "I wish I was a little bit taller" — peaked at No. 13 on the Billboard Hot 100, was certified gold as a single, and earned him a Grammy nomination for Best Rap Solo Performance at the 1996 Grammy Awards. The album also produced the follow-up single "Top of the Stairs" and cemented his status as one of the most distinctive new voices in mid-'90s rap.