Who says you need money to have fun behind the wheel? Some people do, but not Jay Leno. He and comedian Billy Gardell hit the road in Billy's new vintage 1969 Oldsmobile Cutlass convertible. They reminisce about the days when they used to shop at thrift stores, then find themselves at a thrift shop trying on clothes. Jay meets the creators of the Gambler 500, a rally where you "run what you brung." In Jay's case, it's a beat-up 2004 Ford Expedition - the show's old camera car. Jay then hangs out with Donut Media's James Pumphrey who shares his enthusiasm for the MR2, one of the last affordable mid-engine sports car deals of the century. Then, Jay heads to the Los Angeles Slot Car Museum to relive his childhood pastime of racing model cars. Finally, at a car dealership service department, Jay tests regular people on their car knowledge in exchange for cash prizes.