For a brief spell during the late '90s, Crooked I was signed to Virgin. The Long Beach MC appeared on Virgin and Virgin-affiliated compilations like the Caught Up soundtrack ("Girl," with Luniz) and C-Style's 19th Street LBC Compilation ("Gangsta Gangsta," "Bounce to This").
Not a free agent for long, Crooked subsequently fell in with Suge Knight and signed to Death Row, appearing on the Too Gangsta for Radio compilation ("Death Rizzo" and "Gangsta Rap," which also featured Treach and Scarface) and the Dysfunktional Family soundtrack (contributing to nearly a third of its tracks). Though at least one Crooked I mixtape surfaced during the MC's time on the label, a pair of albums -- including Say Hi to the Bad Guy, slated for a 2002 release -- did not. Departed from Death Row by early 2004, Crooked went independent, launching his Dynasty Entertainment label, but legal obstacles prevented him from releasing yet another title of his own. Mixtapes, DVDs, and features continued to pile up, with B.O.S.S. (Beginning of Something Serious) -- at long last, his first official album -- prepared for a 2008 release date.