In 2000, Lil' Flip independently released The Leprechaun catching the attention of DJ Screw, who added the rapper into his loose-knit rap group called the Screwed Up Click. DJ Screw pronounced Lil Flip, "The Freestyle King."
In 2002, Columbia Records offered Flip a contract and Suckafree a distribution deal. 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 Suckafree's CEOs were all about." Lil Flip released his debut studio album Undaground Legend on August 27, 2002. The album was certified Platinum in December 2002. It contained his hit single "The Way We Ball". In 2003 Lil' Flip was also featured in David Banner single "Like A Pimp". Then he also made featured appearance on Yung Wun's charting single "Tear It Up". He also made another appearance on Three 6 Mafia single "Ridin' Spinners" that made the charts. In 2003, he also did a track with Ludacris called "Screwed Up".
In 2004 Lil' Flip released his second major label album U Gotta Feel Me it was his most successful album to date. Lil' Flip's label Columbia restructured Flip ended up at Sony Urban Music which could promote his work better. The first single from the album was "Game Over (Flip)". After that he quickly released his second single, "Sunshine" featuring Lea Sunshine. This album sold 198,000 domestic copies in its first week and was certified double Platinum by August, 2004. Lil' Flip also made an appearance on the "Naughty Girl (Remix)" with Beyoncé in 2004. He was also featured on Chingy's Powerballin' on the remix of Chingy's successful hit single "Balla Baby". In 2004 he also made a remix to his hit single "Game Over (Flip)" which featured Young Buck and Bun B. He also made a guest appearance on Nelly's successful 2004 album "Sweat". He also collaborated with Jim Jones and The Game on the "Certified Gangstas (Remix)" in 2004. In 2005 Lil' Flip & Z-Ro made a collaboration album entitled Kings of the South. Also in 2005 Lil' Flip was featured in Chamillionaire's first single "Turn It Up". He was also featured in the remix of Bun B's single "Draped Up"In 2004 started managing Damienn Jones .
Lil' Flip released his third album I Need Mine in 2007. The album debuted at number 15 on the Billboard 200 with 43,000 copies sold in its first week.
2009–2013 : Major label departure and Ahead of My Time
Lil' Flip left Columbia records and went back to being an independent artist, founding his own label Clover G records. His fourth album Ahead of My Time was originally set to be released as early as 2007, but was pushed back many times and was finally released on July 6, 2010. Lil' Flip released two "album-before-the-album's" in 2009 to help promote the release of Ahead of My Time. The two albums were: Respect Me and Underground Legend 2.
2013–present: The Black Dr. Kevorkian and Mixtapes
Lil' Flip released his fifth album The Black Dr. Kevorkian on October 31, 2013. Selling 10 k its first week. Flip has already released 8 mixtapes this year "White Cup Gang - It'z Just A Texas Thang", "My B-Day 33", "Welcome 2 The Clover" (With Absent), "#Timeless III", "#ScrewLuv", "#Timeless 4", "#Timeless 5" & "#BlackFriday - A Clover G Compilation"
He released his first book Don't Let the Music Industry Fool You, the book was released with a soundtrack album.