One of the early Chicano rappers to make a mark in the West Coast rap scene, Lil Rob gained recognition in the late '90s through various independent labels before finding a stable home at Upstairs Records. His debut album Crazy Life in 1997 established him as a hardcore rapper with a Chicano perspective, leading to subsequent releases and collaborations with the Low Profile Gangsters. In 2002, he made a significant career move with his debut on Upstairs Records, followed by a breakthrough in 2005 with the success of his single "Summer Nights" and the release of Gangster Classics.

Lil Rob's career trajectory saw him rise as a prominent figure in the Chicano rap scene, navigating through different labels and projects before finding success with Upstairs Records. His early work with Familia Records showcased his hardcore rap style and Chicano identity, setting the foundation for his later collaborations and breakthrough moments with hit singles like "Summer Nights." Through his association with the Low Profile Gangsters and his consistent output, Lil Rob solidified his place in the national rap scene, culminating in the release of Gangster Classics in 2005.