Fifteen-year-old Clay (Robert Ri'chard) is very close to his father Frank (Louis Gossett, Jr.), a well-to-do real estate agent who has fought cancer for six years. On his deathbed, he gives his son two assignments that will help him better understand his grandparents. In order to fulfill this mission, Clay puts on a pair of wingtip shoes given to Frank by a fortune teller. The boy is magically transported back to 1962 when his father was a bright teenager. His eyes are opened to Frank's world — his friendships, his close relationship with his sister, and his estrangement from his strict and domineering father. After several time-tripping journeys into the past, Clay is able to set in motion a reconciliation with his extended family and to fully appreciate his father's legacy of love.

Vic Sarin directs this emotionally affecting drama about the importance of walking in another person's shoes in order to understand him. The story also celebrates the healing dynamics of grief and the high and holy calling of fatherhood.