Dito Montiel Director, Writer Robert Downey Jr. Dito Actor Shia LaBeouf Young Dito Actor Chazz Palminteri Monty Actor Dianne Wiest Flori Actor Channing Tatum Young Antonio Actor Melonie Diaz Young Laurie Actor Martin Compston Mike O'Shea Actor Eric Roberts Antonio Actor Rosario Dawson Laurie Actor Adam Scarimbolo Giuseppe Actor Laila Liliana Garro Diane Honeyman Actor Peter Tambakis Young Nerf Actor Scott Michael Campbell Nerf Actor Anthony DeSando Frank Actor Eleonore Hendricks Jenny Actor George Di Cenzo Uncle George Actor Jermel Wilson Yup Yup Actor Trudie Styler Producer Travis Swords Producer Charlie Corwin Producer Clara Markowicz Producer Sting Executive Producer Bobby Sager Executive Producer Peter Sahagen Executive Producer Amanda Mackey Executive Producer, Casting Eric Gautier Cinematographer Christopher Tellefsen Film Editing Jake Pushinsky Film Editing Jonathan Elias Original Music Jody Asnes Production Design Cherish M. Hale Set Decoration Sandra Hernandez Costume Design Melissa Chusid Casting