Traditionally associated with The Black Wall Street Records despite the fact that most the artists on the record label were affiliated with the Bloods, Malone signed with the record label, but later signed with Cash Money Records in 2011, turning down offers from many labels like Def Jam Records, Interscope Records, J Records and Atlantic Records. Glasses Malone was found by the same record executive that found The Game. Along with his signing, he was also given his own imprint, Blu Division. G. Malone debuted with mixtapes The Crack Mixtape (2003) and White Lightnin...Sticks (2005). White Lightnin...Sticks sold 50,000 copies and included the popular street single "Two Hunned".
Glasses Malone appeared in the music video for Tha Dogg Pound's single "Cali Iz Active' and also makes a cameo appearance in the Tech N9ne video "Like Yeah". He also appeared on the soundtrack to Madden 2007 with a song called "Right Now" which was produced by Scott Storch. On August 4, 2006 Glasses Malone appeared on MTV's You Hear It First.
Malone's first album, Beach Cruiser, was originally scheduled to come out on February 20, 2007. However, due to a change in record labels, Malone signed a new deal with Cash Money Records and Hoo-Bangin' Records and his album release scheduled tentatively for April 2008. Two singles from the album debuted in 2008: "Certified" featuring Akon and "Haterz" featuring Birdman and Lil Wayne. His album will now be release on Aug. 29th 2011. although it was leaked on the internet on Aug. 24.
In late 2009, Malone accompanied Tech N9ne and hip-hop supergroup Slaughterhouse on the K.O.D Tour. Malone was featured on former Cash Money R&B singer TQ's 7th studio album Kind of Blue in 2010.