Plot
In 1918 Harlem, small-time gambling operator Sugar Ray is nearly killed by a disgruntled customer, but his young errand boy, Vernest Brown, shoots the man dead. Discovering that Vernest is an orphan, Ray takes him in and raises him as his son.
In 1938, the now-affluent Ray and Vernest—known as Quick—run the upscale Club Sugar Ray, with gambling and dancing in the front and a brothel in the back. The club's success threatens the business interests of ruthless white gangster Bugsy Calhoune, who sends corrupt police sergeant Phil Cantone to demand a majority of the weekly earnings. Realizing this will destroy the club, Ray proposes relocating to another city, but Quick is eager to confront Calhoune. Ray chastises him for his reckless immaturity, warning that such defiance will only get him killed. Still, Ray suggests a scheme to strike back before leaving: on the night of a much-anticipated boxing match between their friend, world heavyweight champion Jack Jenkins, and Michael Kirkpatrick, Ray's crew will rob the betting houses—most of them owned by Calhoune—of more than $750,000 in cash. Ray and his associates also wager on Kirkpatrick to win, convincing Calhoune that Jenkins will throw the fight and leading him to stake $500,000 on Kirkpatrick.
After Calhoune has his enforcer Tommy Smalls murdered for embezzling funds, Quick visits Smalls' apartment in search of information but leaves upon discovering his corpse. Smalls' brother Reggie sees Quick leaving and assumes he is the killer. Quick meets Calhoune's Creole mistress, Dominique LaRue, for a romantic dinner, unaware that Calhoune is accompanying her. Calhoune offers him a job managing the Pitty-Pat Club, which Quick declines. Outside, Quick is ambushed by Reggie and his friends; he kills them in self-defense, believing they were sent by Calhoune to assassinate him. Later, Calhoune sends Dominique to seduce Quick. Suspicious, Quick finds a gun hidden in her bed and unloads it. When Dominique, unaware, tries to use the weapon against him, Quick shoots her dead. Ray sends Quick into hiding, while Calhoune retaliates by having the club destroyed.
Ray learns that Calhoune's bagman, Richie Vento, will be collecting the betting cash. His friend Madame Vera arranges for one of her escorts, Sunshine, to seduce Richie and persuade him to let her accompany him on the collection. Richie gathers the money and stores it in his car, placing it beside Sunshine's identical bag. An arranged car crash allows Ray and Quick, disguised as policemen, to step in. They seize the money bag, claiming Sunshine is a heroin dealer and that the bag holds narcotics. Two white officers then arrive, dismiss Ray and Quick, and take Sunshine and the bag into custody. Cantone, who has been overseeing the delivery, follows Ray and Quick to an abandoned bank and confronts them. They reveal they had anticipated his involvement, trap him inside the vault, and promise to have him released in a few days.
Calhoune realizes he has been deceived when Jenkins easily defeats Kirkpatrick. He returns home in a rage after also learning that Ray's crew have destroyed the Pitty-Pat. Richie unknowingly delivers Sunshine's bag to Calhoune, who discovers it is filled with parcels of sugar and deduces that Ray is behind the scheme. Vera, apparently fearful for her safety, visits Calhoune and claims that Ray and Quick are at Ray's house. Calhoune leads his men there, but they trigger hidden explosives that kill them all.
On the outskirts of Harlem, Ray and Quick pay off the white officers for their part in the scheme and divide the stolen money. Knowing they can never return, yet believing there is nowhere like Harlem, Ray lingers on the skyline one last time before departing with Quick and their friends to begin a new life.
