Unlike his albums released under the name Dre Dog, Cocaine Raps had deeper production values. Raven in My Eyes was noted for emphasizing "sequencers and keyboards that buzz and whine" over live instrumentation, as reviewed by Todd S. Inoue of the news magazine Metroactive. That year, he founded his own record label, Dogday Records. Nickatina explained in an interview with Strivin' magazine that his name change was "for the better" and that he raps because he feels that he is talented enough to do so but not for the sake of popularity.
Soon afterwards, his following three albums, Tears of a Clown (1999), Daiquiri Factory: Cocaine Raps, Vol. 2, The Unreleased [Sold Exclusively at shows and appreances] and These R the Tales (the latter three in 2000) made him more well-known in the West Coast underground rap scene.Mosi Reeves of the San Francisco Bay Guardian noted Nickatina's popularity at a CD release party for another underground Bay Area rapper/producer, Smoov-E; Reeves called Nickatina "a quick-witted rapper who spits as hard as Kurupt does".
A combo CD/movie project, Conversation With A Devil, followed in 2003. Lindsay Welnick, a music critic for SF Weekly, regarded the film as a knockoff of the classic gangster movie Scarface. Nate Denver for the SF Bay Guardian praised the album, though. Another album, The Gift followed in 2005, when the newspaper SF Weekly named Nickatina the "Best Local Hip Hop Legend" of that year. In 2005, Nickatina also won the first annual Bay Area Raps Awards for Best Underground Artist. In 2008, he released A Tale Of Two Andres with Mac Dre. Although they released only two songs together, they were close friends and the album was a tribute to his memory.