Russell Crowe Jackson Healy Ryan Gosling Holland March Angourie Rice Holly March Margaret Qualley Amelia Kuttner Kim Basinger Judith Kuttner Yaya DaCosta Tally Matt Bomer John Boy Keith David Older Guy 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 Maddie Compton Janet Garrett Carpenter Buddy Sala Baker Bodyguard (uncredited) Carson Meyer Bartender at Mexican Restaurant Michael Beasley Bartender at Car Show Gary Wolf Flight Deck Bartender