Andra Day as Billie Holiday

Trevante Rhodes as Jimmy Fletcher

Garrett Hedlund as Harry Anslinger

Leslie Jordan as Reginald Lord Devine

Miss Lawrence as Miss Freddy

Adriane Lenox as Mrs. Fletcher

Natasha Lyonne as Tallulah Bankhead

Rob Morgan as Louis McKay

Da'Vine Joy Randolph as Roslyn

Evan Ross as Agent Williams

Tyler James Williams as Lester 'Prez' Young

Tone Bell as John Levy

Blake DeLong as Agent Carter

Dana Gourrier as Sadie

Melvin Gregg as Joe Guy

Erik LaRay Harvey as James Monroe

Ray Shell as Carl The Drummer

Dusan Dukic as Joe Glaser

Koumba Ball as Lucille

Kate MacLellan as Working Class Woman

Kwasi Songui as Working Class Man

Letitia Brookes as Velva

Warren 'Slim' Williams as Bobby Tucker

Orville Thompson as Auditioning Sax Player

Jeff Corbett as Congressman JP Thomas

Damian Joseph Quinn as Roy Cohn

Robert Alan Beuth as Congressman J. Rankin

Randy Davison as Senator J. McCarthy

Kevin Hanchard as Louis Armstrong

Jono Townsend as Guitar Player

Morgan Moore as Bass Player

Arlen John Bonnar as Priest

Furly Mac as Elevator Attendant

Andrew Zadel as Agent McDermott

Tristan D. Lalla as Mr. Jordon Green

Alex Bisping as Bailiff #1

Don Anderson as Judge Ganey

Amanda Strawn as Gloria

Charleine Charles as Shirley

Sylvia Stewart as Stink-Eye Inmate

Daphné Archer as Jail Dishwasher

Anita Lee as Fighting Woman

Tony Chao as Fighting Man

Linda Sauvé as Receptionist

Alain Goulem as Ed Fishman

Ramona Clyke as Miss Mona

Laurent Beaudin as Ed Fishman's Assistant

Alika Autran as Martha Anslinger

Kim Feeney as Lady In Audience

Diana Carmen Ratycz as Carnegie Fan

Richard Jutras as Uptown Restaurant Maître d'

Jonathan Higgins as Defense Lawyer Erlich

Marc Essertaize as Bailiff #2

Nealla Gordon as Courthouse Reporter

Len Blavatnik as Club Owner

Christopher Ricardo Price as Drug Dealer

Taryn Brown as Billie (10 years old)

Zuri Hawkins as Little Girl in Brothel

Elizabeth Eveillard as Prostitute 1923

Clauter Alexandre as Husband

Penande Estime as Hanging Woman

Elikya Tupula as Young Daughter

Nefertari Zanyah Brewster-Griffith as Older Daughter

Joe Cobden as George Jessel

Ronda Louis-Jeune as Jimmy's Girlfriend

Maxime Paradis as Producer

Sarah Levesque as Nurse

Donald Fullilove as Additional Voices (voice)