* Scott Thompson as Bobcaygeon, the main character and a middle-aged man struggling to find purpose in life.
* Martha Burns as Louise, Bobcaygeon's long-time partner, who is supportive but often frustrated by his indecision.
* Paul Gross as Doug, Bobcaygeon's friend and business partner, who is successful but often condescending.
* Jennifer Irwin as Susan, Bobcaygeon's ex-wife, who is now married to a wealthy businessman.
* Debra McGrath as Betty, Bobcaygeon's mother, who is a strong and independent woman.
* Don McKellar as The Mayor, the eccentric and corrupt mayor of Bobcaygeon.
* Liane Balaban as Elaine, a local woman who catches Bobcaygeon's eye.
The film also features several other actors in smaller roles, including:
* David Fox
* Michael Therriault
* Christine Horne
* Jonathan Sousa
* Dan Redican
This is not an exhaustive list, but it includes the main actors and actresses who appear in the film.