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Roberto Flores was born in the La Colonia area of Eden Gardens, a Mexican founded neighborhood near Solana Beach, California. In the early 1990s, he began performing under the name Lil Rob and the Brown Crowd, and recorded a single titled "Oh What a Night in the 619." Though it did not chart, it was later featured on his 1997 debut album Crazy Life, with the title shortened to "Oh What a Night." In 1994, his chin was shattered when he was shot in the jaw and in the eye later.