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Jon Hamm as Bob Callahan Annabelle Wallis as Rebecca Crosby Courtney Brown as Nurse (uncredited) Donald K. Overstreet as Bar Patron (uncredited) Jake Johnson as Randy 'Chilli' Cilliano Maxwell Ross as Teen Jerry Legend Williams as Young Kevin Brian Dennehy as Mr. Cilliano Vince Pisani as Wedding Planner Loren Lott as Sable's Girlfriend Carrie Brownstein as Therapist (uncredited) Ed Helms as Hogan 'Hoagie' Malloy Steve Berg as Louis Jeremy Renner as Jerry Pierce Isla Fisher as Anna Malloy Melissa LeEllen as Mall Patron (uncredited) Joey Thurmond as Wedding Guest (uncredited) Hannibal Buress as Kevin Sable Leslie Bibb as Susan Rollins Th'Yana Star as Young Cheryl Thomas Middleditch as Dave Indiana Sifuentes as Mexican Jerry Kate Kneeland as Wedding Caterer Brayden Benson as Young Jerry Kevin Tyler Moody as Teen Randy Tyler Crumley as Young Randy Lil Rel Howery as Reggie Jock McKissic as Marvin Al Mitchell as AA Member Kurt Yue as Doctor Yuen Leslie Sides as Freedom Atlantic Employee (uncredited) Rashida Jones as Cheryl Deakins Jaren Lewison as Teen Hoagie Braxton Alexander as Young Bob Sebastian Maniscalco as Pastor Trayce Malachi as Young Boy in Mall Tatum Price as First Class Passenger (uncredited) Braxton Bjerken as Young Hoagie Elijah Marcano as Teen Bob Nora Dunn as Linda Malloy Jim Esposito as Martin - Neighbor

Richard Brener Executive Producer Christopher H. Warner Unit Production Manager Rich Delia Casting Todd Garner Producer Jane Oshita Stunts Walter Hamada Executive Producer Rob McKittrick Screenplay Jeff Tomsic Director Germaine Franco Original Music Composer Mark Miscione Stunts Tara Feldstein Bennett Casting Director