Chi-Raq

as Chicago police officer

as Private Wilbur

as Miss Helen Worthy

as Mr. Doctor Aesop

as Chief Riptide

as Rasheeda

as Police Officer

as Barbara

as Candy

as Jah

as Chicago Cop

as Mayor McCloud

as Pindar

as Morris

as General King Kong

as Joe the Supervisor

as Blue Monday

as Marcy

as Fifi

as National Guard Singer / Dancer

as Grey

as Spinna

as Sugar Pie

as Tee-Tee

as Dania

as Tereus

as Althea

as Commissioner Blades

as Chifon

as Bacchos

as Olympia

as Besomighty

as Irene

as National Guard

as Fr. Mike Corridan

as J Dog Englewood

as National Guardsman

as Hecuba

as Ajani

as Divine

as Sergeant Toney

as Police officer

as Indigo

as Channel 7 News Reporter

as Cafe Waiter

as Michelle

as Demetrius 'Chi-Raq' Dupree

as Secretary to Mayor McCloud

as Cairo

as Dancer

as Red, White, and Blue Insurance Salesman

as Pretty Pink

as Dolmedes

as Private Alto

as Big Mike

as Ole Duke

as Lorde

as Lysistrata

as Apollo

as Lucy

as Big Thelma

as Electra Johnson

as T-Money

as Oedipus

as Sean 'Cyclops' Andrews

as Armonty

as Tiny Tony

as Kenya