Amid the flourishing underground rap scene of Houston, Lil' Flip rose to quick and prosperous fame after his independently released 2000 album The Leprechaun broke through to a national audience, prompting the young rapper's signing to Universal Records soon after. Nicknamed the Freestyle King, Flip as a teen initially won the attention of the immortalized DJ Screw, who ushered the rapper into his loose-knit Screwed Up Click. The affiliation brought instant respect for Flip throughout Texas as well as the greater South, and his Leprechaun album capitalized on that, moving an impressive number of units for an independently released album. The album's slowly mounting yet ultimately broad reach and Flip's youthful appeal attracted Universal Records, who signed the barely 20 year old to a major-label contract in 2002 and released Undaground Legend later in the year. Driven by the lead single, "The Way We Ball," as well as a remix of "I Can Do Dat," a hit previously released on The Leprechaun, the album extended Flip's audience nationally and heralded him as one of the South's most promising young rappers of the early 2000s.