In the Biggest Little City in the World, Reno Nevada, lives a lovable loser, Harold James Clark. 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. Harold looks at a half filled glass and is simply amazed that there is even a glass. This Elvis wannabe finally meets his dream girl, Wanda Livingston. She's just run away from Vegas and her 80's rocker boyfriend, Jake Salamander. Never-mind her lack of waitressing skills, Harold gets her a job at the Wagontrain anyhow, and shows her the ropes. When Jake shows up in Reno Wanda decides to give him another chance. Meanwhile, Harold and Wanda become close real fast. Too close for Wanda. Not close enough for Harold. He's in Love... And ready to pop the question.

The film follows a $20 bill from its ATM birth to its eventual demise. Along the way, the note weaves in and out of the lives of a street person, an aspiring writer, a stripper, two thieves, and many others in surprising and inventive ways.

When Madea catches sixteen-year-old Jennifer and her two younger brothers looting her home, she decides to take matters into her own hands and delivers the young delinquents to the only relative they have: their aunt April. A heavy-drinking nightclub singer who lives off of Raymond, her married boyfriend, April wants nothing to do with the kids. But her attitude begins to change when Sandino, a handsome Columbian immigrant looking for work, moves into April's basement room. Making amends for his own troubled past, Sandino challenges April to open her heart. And April soon realizes she must make the biggest choice of her life: between her old ways with Raymond and the new possibilities of family, faith ... and even true love.