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) for which he won best actor at the Slamdance Film Festival; Reichardt's Wendy and Lucy (2008), Mickle's Mulberry Street (2006) and Stake Land (2010), Joe Swanberg's All the Light in the Sky (2011), and Ted Geoghegan's We Are Still Here.