Jeffrey Wright Thelonious 'Monk' Ellison Leslie Uggams Agnes Ellison Erika Alexander Coraline John Ortiz Arthur Sterling K. Brown Clifford Ellison Tracee Ellis Ross Lisa Ellison Issa Rae Sintara Golden Myra Lucretia Taylor Lorraine Raymond Anthony Thomas Maynard Adam Brody Wiley Valdespino John Ales Leo Patrick Fischler Mandel Carmen Cusack Gilda Okieriete Onaodowan Van Go Jenkins Keith David Willy the Wonker Kate Avallone Woman on Patio Dustin Tucker Phillip David De Beck Dr. Bulger Michele Proude Bulger's Nurse Miriam Shor Paula Baderman Greta Quispe Luz Borquez J.C. MacKenzie Carl Brunt Neal Lerner Wilson Harnet Jenn Harris Ailene Hoover Bates Wilder Jon Daniel Sigmarsen Michael Cyril Creighton John Bosco Celeste Oliva Dr. Tiefel Megan Robinson Kenya Dunston Michael Malvesti Plainclothes Cop Samantha Gordon Gaby