Jeffrey Wright as Thelonious 'Monk' Ellison

John Ortiz as Arthur

Erika Alexander as Coraline

Leslie Uggams as Agnes Ellison

Sterling K. Brown as Clifford Ellison

Skyler Wright as Brittany

John Ales as Leo

Patrick Fischler as Mandel

Carmen Cusack as Gilda

Joseph Marrella as Matthew Wilson

Stephen Burrell as Jordan Phillips

Issa Rae as Sintara Golden

Nicole Kempskie as Sintara's Moderator

Becki Dennis as Clinic Receptionist

Tracee Ellis Ross as Lisa Ellison

Myra Lucretia Taylor as Lorraine

Ryan Richard Doyle as Ned

Kate Avallone as Woman on Patio

Dustin Tucker as Phillip

Michael Jibrin as Jelani

Michele Proude as Bulger's Nurse

David De Beck as Dr. Bulger

Okieriete Onaodowan as Van Go Jenkins

Keith David as Willy the Wonker

Miriam Shor as Paula Baderman

Raymond Anthony Thomas as Maynard

Greta Quispe as Luz Borquez

J.C. MacKenzie as Carl Brunt

Elle Sciore as Layne

Adam Brody as Wiley Valdespino

Justin Andrew Phillips as Arthur's Intern

Neal Lerner as Wilson Harnet

Jenn Harris as Ailene Hoover

Bates Wilder as Jon Daniel Sigmarsen

Jason Armani Martinez as Nursing Home Orderly

Michael Cyril Creighton as John Bosco

Celeste Oliva as Dr. Tiefel

Megan Robinson as Kenya Dunston

Christopher Barrow as Burt

Alexander Pobutsky as Kenny

Tokunbo Joshua Olumide as Alvin

Chhoyang Cheshatsang as Wiley's Assistant

Michael Malvesti as Plainclothes Cop

Samantha Gordon as Gaby (uncredited)

Jason Armani Martinez as Nursing Home Orderly

Anu Bamidele as Teen (uncredited)

Russell J. Gannon as Man At Book Fair (uncredited)

Heidi Garza as Coffee Customer (uncredited)

Josh Habib as Lunch Patron (uncredited)

Ian Dylan Hunt as Book-signing Guest / Awards Dinner Guest (uncredited)

Nahna James as Book Convention Attendee (uncredited)

Emily Kokidko as Student (uncredited)

Erin McAnespie as College Student (uncredited)

Adrian M. Mompoint as Jeff (uncredited)

Kevin Pitcairn as Boston Restaurant Patron (uncredited)

Anne Reardon as Waitress (uncredited)

Cheryl Lee Thorup as Personal Assistant (uncredited)