Three years later, he secured a joint venture with Columbia Records, achieving mainstream recognition for his 2004 singles "Game Over" and "Sunshine", which peaked at numbers 15 and two on the Billboard Hot 100, respectively.

Impressed by his skills, DJ Screw invited Lil' Flip to join the group and bestowed upon him the title of "The Freestyle King".

Reflecting on the partnership, Flip stated: "We felt that they not only respected what we'd already accomplished on our own, but they also saw the big picture of what me as an artist, and Hump and I as Sucka Free's CEOs were all about.

"On 27 August 2002, Lil' Flip released his second album, Undaground Legend, which achieved platinum certification by December of the same year.

In 2003, he appeared on a number of notable tracks, including "Like a Pimp" by David Banner, "Tear It Up" by Yung Wun, and "Ridin' Spinners" by Three 6 Mafia.

Following a restructuring at his label, Columbia Records, he transitioned to Sony Urban Music, which he believed would provide stronger promotional support.

Additionally, he contributed to the 2 Fast 2 Furious soundtrack with the song "Rollin' on 20s", featuring fellow Houston rapper Yung Redd.

Lil' Flip’s planned fifth studio album, Ahead of My Time, was originally slated for release as early as 2007 but faced numerous delays.

Later that year, on 24 December 2009, Lil' Flip released his first fully independent album, Underground Legend 2, through his self-owned label Clover G Records.