Kellie Pickler knew early on that by earning a few extra bucks she'd really be helping her grandparents, who took charge of raising her when she was 11-years-old. So she got a job as a car hop at a Sonic Drive-In serving burgers, hot dogs and fries when she was 17. While the singer learned a lot about customer service, she's yet to show off the roller skating skills she picked up onstage. Pickler was also on her school's varsity cheerleading team, and sheentered in a number of beauty pageants during her teenaged years.