In 1999, Lil' Flip signed his first record deal with independent Houston, Texas label Sucka Free. On July 18, 2000, Lil' Flip released his debut album The Leprechaun, catching the attention of DJ Screw, who led Flip to join his rap group, Screwed Up Click. DJ Screw proclaimed Lil' Flip "The Freestyle King".^[4]

In 2002, Columbia Records offered Flip and Suckafree a joint venture recording contract and distribution deal. Flip stated that: 

"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."

Lil Flip released his second album Undaground Legend on August 27, 2002. The album was certified platinum in December 2002. It contained the single "The Way We Ball". In 2003, Lil' Flip was also featured on the singles "Like a Pimp" by David Banner, "Tear It Up" by Yung Wun, and "Ridin' Spinners" by Three 6 Mafia. That same year, Flip guest appeared on Ludacris' song "Screwed Up" from his album Chicken-N-Beer.

In 2004, Lil' Flip released his third album & first double-disc album U Gotta Feel Me. Lil' Flip's label Columbia restructured and Flip ended up at Sony Urban Music, which he believed could promote his work better. The first single from the album was "Game Over (Flip)", followed by his second single, "Sunshine" featuring Lea Sunshine. This album sold 200,000 copies in its first week, and was certified platinum by the Recording Industry Association of America (RIAA) in 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 titled Kings of the South. Also in 2005, Flip guest featured in Chamillionaire's debut single "Turn It Up", and featured on the remix of Bun B's single "Draped Up".^[4] Lil' Flip was also featured on the 2 Fast 2 Furioussoundtrack, on its track "Rollin' on 20s" (featuring fellow Houston rapper Yung Redd).

In 2007, Lil' Flip left Columbia records and founded his own label, Clover G Records. The label was launched as an imprint of Asylum and Warner Bros.; its first release was his third album and second double-disc album, I Need Mine, which released on March 27, 2007. The album debuted at number 15 on the Billboard 200, with 43,000 copies sold in its first week. Only two singles were released from the album, "What It Do" and "Ghetto Mindstate (Can't Get Away)".

His planned fifth album Ahead of My Time was originally set to be released as early as 2007, but was pushed back many times. Lil' Flip released two "album-before-the-album's" in 2009 to help promote the release of Ahead of My Time.^[5][6] On September 29, 2009, Lil' Flip would release his fifth album titled Respect Me to promote Ahead of My Time, it would be distributed by High Powered Entertainment & E1 Music. On December 24, 2009, Lil' Flip would release his first independent album titled Underground Legend 2 to promote Ahead of My Time, it would be distributed independently by Lil' Flip's self-owned label Clover G Records.^[7]

On July 6, 2010, Lil' Flip would release Ahead of My Time as his second independent album, and debuted his artist Damienn jones "Beauty and the Beast" album, it would be distributed independently by Lil' Flip's self-owned label Clover G Records.

On October 31, 2013, Lil' Flip released his third independent album The Black Dr. Kevorkian, it would also be distributed independently by Lil' Flip's self-owned label Clover G Records & would sell over 10,000 copies its first week.

On March 17, 2015, Lil' Flip released his sixth album titled El Jefe, it was distributed by SoSouth Records.^[8][9] The lead single from the album was titled "Game Over II", which was sequel to his single "Game Over (Flip)".^[10] The second single from the album, was titled "In My Pimp C Voice", which was a dedication song towards deceased artist Pimp C.^[11] The third single from the album, was titled "Bestfriend" the single would feature artist's E.J. Carter & Rev City.^[12][13]

Clover G Records or Clover G La Familia is a record label owned by Houston, Texas rapper Lil' Flip, it was created in 2004.

In 2004 Lil' Flip released his shoe line titled "Clover Footwear" which is branded off his self-owned label Clover G Records.^[14] Lil' Flip also has a fashion clothing line titled "Clover G Clothing" which is also branded off his self-owned label Clover G Records.^[15]

On April 15, 2014, Lil' Flip released his first book titled Don't Let the Music Industry Fool You!, the book was released with a soundtrack album.^[16][17]

• 2000: The Leprechaun
• 2002: Undaground Legend
• 2004: U Gotta Feel Me
• 2007: I Need Mine
• 2009: Respect Me
• 2009: Underground Legend 2
• 2010: Ahead of My Time
• 2013: The Black Dr. Kevorkian
• 2015: El Jefe
• 2016: The Art of Freestyle
• 2018: King^[18]
• 2018: Life^[19]
• 2019: The Art of Freestyle 2^[20]
• 2019: The Music Machine^[21]
• 2020: Feelings^[22]
• 2020: No Feelings^[23]
• 2020: The Leprechaun 2^[24]
• 2022: The Art of Freestyle 3^[25]
• 2022: Fondren Flip^[26]

• 2005: Kings of the South (with Z-Ro)
• 2006: Connected (with Mr. Capone-E)
• 2007: Still Connected (with Mr. Capone-E)
• 2008: All Eyez on Us (with Young Noble)
• 2009: Certified (with Gudda Gudda)
• TBA: Kings of the South II (with Z-Ro)
• 2022: Whip that work (with Rob Run Corleone)

• 2014: Don't Let the Music Industry Fool You