Shaking the Tree is an ensemble dramedy about four male friends living in Chicago, pushing 30, who help each other through a series of crises. Barry (Arye Gross) is a real estate salesman and a huge White Sox fan who's nervous about his impending wedding to Michelle (Christina Haag). When he presses her about her sexual past, he finds out she once slept with one of his pals. Duke (Steven Wilde, who co-wrote the script with director Duane B. Clark) was forced to give up boxing due to an injury, and is unhappy with his life as a womanizing bartender. Sully (Gale Hansen) comes from a wealthy family. He is also a womanizer, and his gambling problem is spiraling out of control. When he loses ten grand to some shady characters, his family refuses to bail him out. Michael (Doug Savant of Melrose Place) is a college professor with a massively pregnant wife, Kathleen (Courteney Cox), and his fear of becoming a father leads him to consider an affair with a seductive student, Brigette (played by actor Gale Hansen's wife, Brittney Hansen). After Cox became a success on television with Friends, the film was re-released on video with the photo on the box changed to feature the actress prominently, although she plays a supporting role in the film.