As a character actor, Fessenden has appeared in numerous films, including Martin Scorsese's Bringing Out the Dead (1999), Steve Buscemi's Animal Factory (2000), Brad Anderson's Session 9 (2001) and Vanishing on 7th Street (2010), Jim Jarmusch's Broken Flowers (2005), Neil Jordan's The Brave One (2007), McQuaid's I Sell the Dead (2008), Reichardt's Wendy and Lucy (2008), Mickle's Mulberry Street (2006) and Stake Land (2010), and Joe Swanberg's Silver Bullets (2011). Fessenden stars in and has directed the films Habit (1997), Wendigo (2001), and The Last Winter (2006). Fessenden also starred in the Sundance Film Festival pictures River of Grass (1994) directed by Reichardt, and Margarita Happy Hour (2001) directed by Chaiken.