The following are characters who have worked with Omar Little. Omar and his associates make their living robbing drug dealers. For the first three seasons, he mainly targets the Barksdale Organization. Later, he goes after Stanfield Organization, culminating with a robbery of the entire New Day Co-Op. Omar himself never goes after any citizens or non-drug related people along with the rest of his crew who follow him. The others who work with Omar are often Baltimore Stick-Up artists whose motive for siding with Omar is the money associated with robbing stash houses. As Omar is gay, many other members of his crew are also of an LGBT+ background (Omar's boyfriends in addition to Kimmy and Tosha amongst others) while other members are of a heterosexual background and side with Omar due to his feared reputation amongst Baltimore drug dealers.
- Omar Little is a legendary Baltimore stick-up thief who leads others interested in stealing money from known drug dealers. A homosexual, Omar is unanimously disliked and feared by several drug dealers throughout the city as he is often seen ripping off various dealers and their drug stashes. Omar remains on good terms with the Baltimore police however due to his moral code which involves not killing any citizens or tax payers that do not get involved in the drug trade.
- Butchie is a mostly blind bar owner who acts as an advisor and bank for Omar.
- Brandon was Omar's boyfriend in the first season.
- Dante was Omar's boyfriend in the second and third season.
- Renaldo was Omar's boyfriend in the fourth season.
Other members of the crew
- Bailey was a member of Omar's crew in the first season.
- Kimmy is a member of Omar's crew in the second, third and fourth seasons and is Tosha's partner.
- Tosha is a member of Omar's crew in the second and third seasons and is Kimmy's partner.