Major Hit: "Ridin'" (2006)

Other Hit: "Turn It Up" f/ Lil Flip (2005)

In terms of Texas rap getting exposed nationally, Chamillionaire was a little late to the party. But he actually wound up having more success than many of his counterparts from the Lone Star State. "Ridin'" topped the Hot 100, won a Grammy for Best Rap Performance by a Duo or Group, and was nominated (but didn't win) for Best Rap Song. The song also won Best Rap Video at the MTV Video Music Awards, and its ringtone was downloaded over 3 million times.

But if you think he might be a one-hit wonder, think again. Before "Ridin'" rode up the charts, Chamillionaire had been bubbling on the underground for years, and already had another chart hit under his belt with Lil Flip ("Turn It Up"). He would go on to another successful underground run with his Mixtape Messiah series.