Herrera first began selling Chingo mixtapes around 2001 at local stores, flea markets, and wherever else in Texas he could find an audience. His big break came when he seized the opportunity to appear on Power 106's Pocos Pero Locos show in Los Angeles. The syndicated show got his music played throughout the Southwest on Chicano rap forums. Self-released on his own Big Chile Enterprises label, his first album, 2004's The Tamale Kingpin, was heavily anticipated, but by the release of his second album, the following year's 4 President, Chingo had become a regional star. His record sales did not measure up to breakthrough artists on major labels, but his comedic appeal garnered widespread attention, including features on MTV and Telemundo as well as in several hip-hop publications. Some of the attention, however, came from critics who thought of him as just a Latino version of a black Sambo, a racist caricature of Mexican/Chicano culture. And it didn't help that Herrera's Big Chile imprint was also producing products like Chingo bobblehead dolls and hot sauce. Nonetheless, the local hoopla over Chingo translated into a heated contract bidding war among major labels like Bad Boy, Universal, Capitol, and Atlantic. Asylum/Warner won out, signing Big Chile to an $80 million distribution deal in 2006.
Amidst the rising tension concerning the influx of undocumented Latino and Latina immigrants in the late 2000s, Herrera switched the title of his 2007 Asylum debut from Welcome to the Border to They Can't Deport Us All. His concerted promotional effort (which included erecting a billboard of the album title in Houston) drew out all types of backlash from national conservative pundits and local citizens alike. In addition to receiving several death threats, his father's tamale truck, brandishing the album promotional ad, was vandalized, shot at, illegally towed, and then, finally, stolen. They Can't Deport Us All debuted at 11 on the rap charts, containing features from Baby Bash, Pitbull, Paul Wall, and Mistah F.A.B. ~ Cyril Cordor, Rovi