In the Biggest Little City in the World, Reno Nevada lives a lovable loser, Harold James Clark. He cruises the streets in his make shift 1959 Cadillac convertible. He cut off the hard top himself. He's reaching for the stars while he searches for love and hopes to live his dream of becoming full time manager at the Wagontrain Steakhouse. Harold's assistant manager status already leaves him feeling lucky. After a night at the penny slots, Harold meets his dream girl, Wanda Livingston. And after some heartfelt advice from his Father he begins a relentless pursuit to win her over. In a way that only Harold knows how.