The Four Corners of Nowhere (1995)

Duncan, a philosophical nomad hitchhiking across America, grabs a ride to Ann Arbor, Michigan from Toad - a performance artist and purple leisure slacks enthusiast from the suburbs. Toad has recently left his home town to begin a new life in Ann Arbor where his co-dependent, folk-singing sister Jenny lives with her verbally abusive fiancé, a law student named Calvin. Jenny currently sees a suicidal therapist four times a week and armed with her acoustic guitar, drives away patrons from a local coffee house where she slings cappuccinos with her best friend Squeeze. Squeeze is a closet genius whose easy-going outlook and unconditional support keep her live-in boyfriend Hank from the brink. Hank is a painter who can't paint because he spends his time baking delicious pastries and practicing for the Oprah Winfrey Show. In Ann Arbor, the civilians listen to Julian, a sociopathic dee-jay whose frustration and lingering optimism goad him to find the truth by cutting through blind idealism, pop culture, and politically correct bumper stickers. Once in Ann Arbor, Duncan encounters these and other eccentric characters, and through his simple outlook and curiosity, he changes their lives forever.