Cynthia
Cynthia is a twenty-five-year-old social worker. She is married to Sonny-man. Cynthia is a middleclass, educated, African-American woman, whose attitude toward Tommy, like that of Bill and Sonnyman, is arrogant and patronizing. She and Sonnyman meet Tommy in a bar, where they recognize her as the image of a down-and-out woman Bill is looking to paint. They take Tommy to Bill’s apartment without explaining why and allow her to believe that she is being set up with Bill as a romantic interest. Thus, although she and Tommy are both African-American women, Cynthia demonstrates a lack of respect for Tommy, allowing her to be used by a man whose attitude toward her is insulting.

When the men leave, Cynthia and Tommy have a discussion that demonstrates Cynthia’s ideas about how African-American women should behave in their relationships with men. She tells Tommy that she is too coarse and unfeminine and that she should allow men to have the upper hand in her relationships with them. Cynthia also criticizes Tommy for wearing a wig, instead of showing her natural hair. But, as Tommy later points out, the reason she wears a wig is that women like Cynthia make her feel ashamed of being her ‘‘natural’’ self. Cynthia also tells Tommy, ‘‘You have to let the black man have his manhood again,’’ to which Tommy responds, ‘‘I didn’t take it from him, how I’m gonna give it back?’’ Cynthia represents Childress’s vision of the attitude of some educated, middle-class African-American women toward African-American women who are less educated and less privileged than they.

Bill Jameson
Bill Jameson is a thirty-three-year-old artist. He lives in an apartment in Harlem. Bill is working on a ‘‘triptych,’’ or series of three paintings, to represent his ‘‘statement’’ on ‘‘black womanhood’’: ‘‘Black girlhood,’’ an image of innocence and sweetness; ‘‘Wine in the Wilderness,’’ his vision of an idealized ‘‘African queen’’; and a third image, not yet painted, which represents his perception of ‘‘what society has done to our women.’’ For this third picture, which he envisions as a down-andout African-American woman who is ‘‘ignorant, unfeminine, coarse, rude . . . vulgar . . . a poor, dumb chick that’s had her behind kicked until it’s numb,’’ and for whom ‘‘there’s no hope.’’

Bill has been looking for a woman to model for this picture, and during a race riot in Harlem, Bill’s friends bring to his apartment a woman they see as an embodiment of this third image. Bill quickly sees in Tommy this down-and-out, ‘‘hopeless chick’’ he had in mind. He convinces her to allow him to paint her only because she believes he is interested in her for romantic reasons. The next morning, however, Tommy discovers Bill’s true intentions and becomes enraged. She realizes that Bill looks down on her for being less educated and less privileged than he and accuses him of looking down upon the ‘‘masses’’ of the African-American community, although he claims to represent the community through his art. Bill is defensive at first, but, when Tommy blurts out that she loves him, he is moved by this revelation to gain new insight into his art and his vision of African-American womanhood. He realizes that he has been misguided in his approach to art and his attitude toward the African-American community, that he has been ‘‘painting in the dark, all head and no heart.’’ Bill finally understands that Tommy herself represents his ideal vision of the African-American woman, his ‘‘Wine in the Wilderness.’’ He convinces her to stay and pose for a painting to represent her in this new light.

Tommorrow Marie
See Tommy

Edmond Lorenzo Matthews
See Oldtimer

Oldtimer
Oldtimer, in his sixties, is described as ‘‘an old roustabout character.’’ He seems to be an alcoholic without much money, who often mooches off of his neighbors, although he is also friends with them. In the midst of the riot, Oldtimer enters Bill’s apartment with a bundle of loot he claims to have picked up from the street after it was dropped by the rioters. His bundle includes a bottle of whiskey, some salami, and a new suit. He is anxious because the police are looking around in the building, and he is afraid of getting arrested for stealing. Bill reluctantly helps him to hide the bundle, and the two share the bottle of whiskey. Oldtimer is a warmhearted, good-humored man who is clearly much less educated than Bill. Bill explains his series of paintings to Oldtimer as they drink.

When Tommy is brought into the apartment and introduced to Oldtimer, she surprises everyone by asking his real name. Bill, Cynthia, and Sonnyman realize that they don’t even know their friend’s name. He tells them his name is Edmond Lorenzo Matthews. The fact that they didn’t know his name, although they’ve clearly known him for some time, indicates the lack of respect these middle-class, educated people have for one of their elders. Tommy later criticizes them for not showing him more respect. Oldtimer likes Tommy right away and is flattered when she flirts with him. The next day, Oldtimer comes into the apartment and, without thinking about what he is saying, reveals to Tommy that Bill wants to paint her as an image of ‘‘the worst gal in town.’’ He is immediately sorry for saying it, but Tommy is glad to have been told the truth about what Bill thinks of her.

By the end of the play, Tommy helps Bill to gain more respect for Oldtimer as representative of a different generation of African-American men who were given little opportunity for education or financial gain. Bill points out, ‘‘Now there’s Oldtimer, the guy who was here before there were scholarships and grants and stuff like that, the guy they kept outta the schools, the man the factories wouldn’t hire, the union wouldn’t let him join.’’

Sonny-man
Sonny-man is a twenty-seven-year-old writer. He is married to Cynthia. Sonny-man wears a dashiki, an African-style shirt, in style during the 1960s and 1970s, which represents a celebration of African heritage. During the riot, he and Cynthia meet Tommy at a bar and recognize her as the image of a down-and-out woman Bill envisions for his third painting. They bring Tommy to Bill’s apartment without explaining to her what Bill has in mind.

Like Cynthia and Bill, Sonny-man represents the arrogant and condescending attitude some middle- class, educated people hold for those less privileged than they. Like Bill, Sonny-man sees himself as a creative person working for the good of the African-American community as a whole; he intends to ‘‘write the revolution into a novel nine hundred pages long.’’ But his attitude toward Tommy and Oldtimer betrays the fact that he looks down on the ‘‘masses’’ of the African-American community.

Tommy
Tommy is a thirty-year-old woman who works in a dress factory. She lives in an apartment over a store that has been burned in the riot. She has not been allowed back into her apartment and has lost most of her clothing and the money she was saving. Cynthia and Sonny-man meet her in a bar during the riot and bring her up to Bill’s apartment because they have identified her as the type of woman he wants to paint for the third part of his ‘‘triptych.’’ Tommy thinks they are trying to set her up with Bill as a romantic interest and has no idea how they really see her. She likes Bill right away and continues to believe that he has taken a romantic interest in her. Tommy is very intelligent, articulate, and witty but is much less educated than Bill and his friends. She finally agrees to sit for Bill’s painting if he will buy her something to eat. While eating, she accidentally spills soda on her clothing, and he gives her an African throw-cloth to wear as a makeshift dress. While she is changing, she overhears Bill on the telephone talking to an art dealer about his picture of ‘‘Mother Africa’’—Tommy does not see that he is talking about a painting and thinks that he is talking about how beautiful he thinks she is. When Bill sees Tommy in the African wrap without her wig, he is mesmerized by how beautiful she now looks to him. He and Tommy kiss.

The next morning, Tommy is happily making coffee while Bill takes a bath. Oldtimer comes in and reveals to Tommy that Bill intends to paint her as an image of ‘‘the worst chick in town.’’ Tommy, hurt and angry, criticizes Bill and his friends (not including Oldtimer) for looking down on her and the ‘‘masses’’ of the African-American community, who are not as educated or privileged as they. Through her anger, Tommy comes to appreciate herself for the woman that she is, in spite of their degrading attitude toward her. However, she blurts out that she loves Bill, which moves him to realize that she is right in her criticisms. He realizes that Tommy in fact represents his ideal African-American woman, his ‘‘Wine in the Wilderness.’’ He convinces Tommy to stay and pose for his new painting.