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One of the first Chicano rappers to carve out a good niche for himself, Lil Rob established himself amid the West Coast rap scene during the late '90s, jumping around from independent label to independent label before finding a steady home at Upstairs Records, where he enjoyed growing success. He debuted on Familia Records in 1997 with Crazy Life, which established him as a hardcore rapper with a Chicano worldview. Similar albums followed in the years to come, and he associated himself closely with the Low Profile Gangsters, a collective of hardcore Chicano rappers tied to the Low Profile label. Rob's career took a turn in 2002 when he made his Upstairs Records debut, The Album. He stuck with the label in the years to come, enjoying a breakthrough of sorts in 2005, when his "Summer Nights" single got a lot of airplay and brought him more national attention than he had ever experienced previously. The full-length Gangster Classics appeared that same year.