Recurring
Method Man as Rodney, a pimp (seasons 1–2).
Don Harvey as Danny Flanagan, a NYPD patrolman and Alston's partner (seasons 1–2).
Michael Kostroff as Rizzi, a desk sergeant in Alston and Flanagan's precinct (seasons 1–2).
Mustafa Shakir as Mike "Big Mike", a physically imposing man of few words who becomes Vincent's muscle and fiercely devoted friend.
Thaddeus Street as Frankie "Black Frankie", a Vietnam veteran hired by Vincent for security at the parlors.
Genevieve Hudson-Price as Jocelyn Wasserman, Harvey's wife and film assistant.
Anwan Glover as Leon, who runs a diner the characters frequent. His disgust at the treatment of the women by their pimps eventually boils over.
Ralph Macchio as Officer Haddix, a jaded vice cop patrolling Times Square in the corrupt police force of 1970s New York.
Zoe Kazan as Andrea Martino, Vincent's estranged wife.
James Ciccone as Carmine Patriccia, a mob underboss who works out of a Mulberry Street social club in Little Italy and is one rung above Rudy Pipilo.
Will Chase as Jack, a divorced man in his 40s who has a brief relationship with Eileen, unaware she is a sex worker (season 1).
Garry Pastore as Matthew Ianniello, the Genovese Family capo who ran the Times Square porn industry during the 1970s and 1980s.
Carolyn Mignini as Joan Merrell, Eileen's disappointed mother who lives in the suburbs of Queens.
Finn Robbins (season 1), Mikey Moughan (season 2), and Dion Costelloe (season 3) as Adam, Eileen's son who lives with her mother.
E.J. Carroll as "Fat" Mooney, manager of a sex shop owned by Frankie (seasons 1, 3).
Gino Vento as Carlos, driver and bodyguard for mobster Rudy Pipilo (seasons 1–2).
Aaron Dean Eisenberg as Todd Lang, a classically trained, unsuccessful actor who begins working in porn films and quickly finds a home. He befriends Paul Hendrickson and enters a personal/business relationship with him.
Kim Director as Leila Brodie / Shay, a sex worker who works for Rodney and struggles with heroin addiction.
Andrea-Rachel Parker as Bernice, a sensitive and naive young woman. During season 1 Darlene travels home to North Carolina and returns with Bernice. She is "traded" from Larry to Rodney, after Larry deems her too young and not street-ready. She then works at the parlor. In season 2, she becomes the parlor's bartender.
Pernell Walker as Ruby / Thunder Thighs, a thoughtful and opinionated plus-sized African American sex worker (seasons 1, 3).
Tariq Trotter as Reggie Love, a pimp (season 1).
Matthew James Ballinger as Richie "Gentle Richie", a pimp (season 1).
Kat Cunning as Christina Fuego, Frankie's wife (seasons 2–3).
Alysia Reiner as Kiki Rains, a shrewd and successful talent agent who manages Lori (seasons 2–3).
Roberta Colindrez as Irene, who manages a peep show owned by Vincent and the Mob. She helps Shay get sober and initiates a relationship with her (seasons 2–3).
Armand Assante as Mr. Martino, Vincent and Frankie's father (seasons 2–3).
Michael Stahl-David as Kenneth, a boyfriend of Paul's and business partner in his new club (season 2).
Sebastian Arcelus as Dave, a labor activist and associate of Dorothy's (season 2).
Esteban Carmona as Julito, a pimp (season 2).
Jim Parrack as Russell, a film editor who becomes Eileen's boyfriend (season 2).
Taylor Selé as Renton Lowry, a pleasant young man with a Caribbean accent who befriends Darlene and helps her get a job and escape the sex trade (season 2).
Ryan Farrell as Greg Taylor, a Los Angeles talent agent who becomes Lori's personal and professional partner (seasons 2–3).
Michael Gandolfini as Joey Dwyer, Bobby's son (seasons 2–3).
Domenick Lombardozzi as Jack Maple, a highly regarded transit police officer who assists Alston in cleaning up Times Square (season 3).
Kelcy Griffin as Jennifer Preston, a smart young African American cop who attracts the attention of Alston (season 3).
Corey Stoll as Hank Jaffe, a wealthy businessman who dates Eileen (season 3).
Calvin Leon Smith as Reg, a sweet-natured gay African American man who befriends Melissa and looks out for her in the apartment they share (season 3).
Sonia Mena as Xiomara, an assertive Hispanic sex worker who quits Bobby's parlor business and encourages the other women to do the same (season 3).
David Morse as Matthew Rouse, Melissa's long estranged father (season 3).
Paloma Guzman as Pilar, a graffiti artist who initiates a relationship with Abby (season 3).
Ben Livingston as Dr. Steiner, a psychiatrist who owns a sleazy property in Times Square (season 3).
