Luke Wilson Bill Actor Carla Gugino Shelli Actor Imogen Poots Kelly Ann Actor Rafe Spall Reg Whitehead Actor Keisha Castle-Hughes Donna Mancini Actor Peter Cambor Milo Actor Machine Gun Kelly Wes Actor Ron White Phil Actor Luis Guzmán Gooch Guest Star Jacqueline Byers Natalie Shin Guest Star Finesse Mitchell Harvey Guest Star Branscombe Richmond Puna Guest Star Tanc Sade Christopher House Guest Star Ping Wu Ron Guest Star Ryan Beil Dale Guest Star The Head and the Heart Guest Star Winnie Holzman Executive Producer J.J. Abrams Executive Producer Bryan Burk Executive Producer Len Goldstein Executive Producer Cameron Crowe Writer, Director