Jason Reitman Director, Screenwriter, Producer Kate Winslet Adele Actor Josh Brolin Frank Actor Gattlin Griffith Henry Actor Tobey Maguire Adult Henry, Narrator Actor Clark Gregg Gerald Actor Tom Lipinski Young Frank Actor Maika Monroe Mandy Actor J.K. Simmons Mr. Jervis Actor James Van Der Beek Officer Treadwell Actor Brooke Smith Evelyn Actor Dylan Minnette Henry at 16 Actor Brighid Fleming Eleanor Actor Alexie Gilmore Marjorie Actor Lucas Hedges Richard Actor Micah Fowler Barry Actor Lianne Halfon Producer Russell Smith Producer Helen Estabrook Producer Steven Rales Executive Producer Mark Roybal Executive Producer Michael Beugg Executive Producer Jeffrey Clifford Executive Producer Eric Steelberg Cinematographer Dana E. Glauberman Film Editing Rolfe Kent Original Music Steve Saklad Production Design Mark Taylor Art Director Tracey Doyle Set Decoration Danny Glicker Costume Design Suzanne Smith Casting Jessica Kelly Casting