Cast Bud Cort - John Doe Jersey Barret Hackney - Stygian Triplet Jared Pfennigwerth - Stygian Triplet Kitao Sakurai - Stygian Triplet George Carlin - Cardinal Ignatius Glick Betty Aberlin - Nun Matt Damon - Loki Ben Affleck - Bartleby Dan Etheridge - St. Stephen's Priest Linda Fiorentino - Bethany Sloane Derek Milosavljevic - Kissing Man Lesley Braden - Kissing Woman Brian O'Halloran - Grant Hicks Janeane Garofalo - Liz Bryan Johnson - Protestor #1/Steve-Dave Pulasti Walter Flanagan - Protestor #2/Walt Grover, the Fanboy Jason Lee - Azrael Nancy Bach - Mrs. Reynolds Alan Rickman - Metatron Armando Rodriguez - Waiter Jason Mewes - Jay Kevin Smith - Silent Bob Jeff Anderson - Gun Salesman Scott Mosier - Smooching Seaman Monica Hampton - Seaman Smoocher Chris Rock - Rufus Salma Hayek - Serendipity Dwight Ewell - Kane, Gang Leader Benjamin J. Cain Jr. - Gangster #1 Richard Baderinwa - Gangster #2 Javon Johnson - Gangster #3 Derrick Sanders - Gangster #4 Mark Joy - Whitland Linda Levine - Miss Price, Woman in Boardroom Ethan Suplee - Noman the Golgothan (voice) Guinevere Turner - Bus Station Attendant Jonathan Gordon - Blanket Boy on Train Matthew Maher - Bartender Nancy Mosser - Gov. Elizabeth Dalton Robert Holtzman - Officer McGee Alanis Morissette - God