Jeffrey Wright Thelonious 'Monk' Ellison John Ortiz Arthur Erika Alexander Coraline Leslie Uggams Agnes Ellison Sterling K. Brown Clifford Ellison Skyler Wright Brittany John Ales Leo Patrick Fischler Mandel Carmen Cusack Gilda Issa Rae Sintara Golden Becki Dennis Clinic Receptionist Tracee Ellis Ross Lisa Ellison Myra Lucretia Taylor Lorraine Kate Avallone Woman on Patio Dustin Tucker Phillip Michael Jibrin Jelani Michele Proude Bulger's Nurse David De Beck Dr. Bulger Okieriete Onaodowan Van Go Jenkins Keith David Willy the Wonker Miriam Shor Paula Baderman Raymond Anthony Thomas Maynard Greta Quispe Luz Borquez J.C. MacKenzie Carl Brunt Adam Brody Wiley Valdespino 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 Alexander Pobutsky Kenny Michael Malvesti Plainclothes Cop Samantha Gordon Gaby (uncredited) Keith David Jeffrey Wright Thelonious 'Monk' Ellison John Ortiz Arthur Erika Alexander Coraline Leslie Uggams Agnes Ellison Sterling K. Brown Clifford Ellison Skyler Wright Brittany John Ales Leo Patrick Fischler Mandel Carmen Cusack Gilda Issa Rae Sintara Golden Becki Dennis Clinic Receptionist Tracee Ellis Ross Lisa Ellison Myra Lucretia Taylor Lorraine Kate Avallone Woman on Patio Dustin Tucker Phillip Michael Jibrin Jelani Michele Proude Bulger's Nurse David De Beck Dr. Bulger Okieriete Onaodowan Van Go Jenkins Keith David Willy the Wonker Miriam Shor Paula Baderman Raymond Anthony Thomas Maynard Greta Quispe Luz Borquez J.C. MacKenzie Carl Brunt Adam Brody Wiley Valdespino 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 Alexander Pobutsky Kenny Michael Malvesti Plainclothes Cop Samantha Gordon Gaby (uncredited) Keith David