Russell Crowe Jackson Healy Ryan Gosling Holland March Angourie Rice Holly March Matt Bomer John Boy Margaret Qualley Amelia Kuttner Yaya DaCosta Tally Keith David Older Guy Kim Basinger Judith Kuttner Beau Knapp Blueface Lois Smith Mrs. Glenn Jack Kilmer Chet Murielle Telio Misty Mountains Gil Gerard Bergen Paulsen Daisy Tahan Jessica Lance Valentine Butler Kid on Bike Ty Simpkins Bobby Hannibal Buress Bumble Yvonne Zima Red Thompson Gary Weeks Officer McMillan Lexi Johnson Pocahontas Matthew Warzel Bartender at Sid's Chloe Hurst Exotic Girl at Sid's Steve Wilder Perry the Lawyer Karrueche Tran Tally-in-Porn Dominic Bagarozzi Paulsen-in-Porn Joanne Spracklen Healy's Ex Wife Tammi Arender Reporter Rebecca Dalton Rusk Fred's Widow Terence Rosemore Bourbon Bartender Greg Lindsay Stand Up Comic Joshua Hoover Dork Sala Baker Bodyguard (uncredited) Michael Beasley Bartender at Car Show Rachele Brooke Smith Party Girl Kimberly Battista Spoon Girl (uncredited) Patti Schellhaas LA Traffic Jam Driver (uncredited) Robert Downey Jr. Sid Shattuck (uncredited)