Why Are You Ranking: August Wilson’s Best Ex-Con, Could-Be-Criminals or Soon to Be Convicted Characters Listed From His ‘Twentieth Century Cycle’ of Plays

The bard of The Hill District in Pittsburgh presents characters with past jail terms or those who may face the penitentiary.

A symbol of captivity

Upon hearing the name August Wilson, the responses usually reflect that of the definition of his first name. Illustrious. Esteemed. Respected. The late poet and playwright born Frederick August Kittel Jr. spent decades carving out an immense sculpture of black America. His powerful writing style and relentless attention to bearing witness to the truth allowed him to delve into the psyche of African Americans. One key characteristic found in almost all of his Twentieth Century Cycle is the appearance of at least one character that either is a suspected criminal, an ex-convicted felon, or is assumed headed to prison. As of this writing, blacks make up about 12 percent of the general population of America and at the same time 40 percent of the prison populace. Mr. Wilson, in his plays, seeks to find the meaning at the root of this disparity. Through his work, he’s been able to show the humanity of men of color who have been affected by the justice system. He has also displayed them as angry, vicious monsters. But the underlying theme to all of his plays is the idea of what it's like to be free in a world that expects you to either go to a cage, stay in a cage, or go back to one. Every line of monologue that is spouted by a man who has or will (presumably) experience the cold hand of justice brings his consciousness to the fore. So, prepare to dance the juba and make sure that you remember your ancestors (Aunt Ester) for Why Are You Ranking: August Wilson’s Best Drawn Ex-con, Could-be-criminals or Soon to be Convicted Characters from his ‘Twentieth Century Cycle’ of Plays. ***(Spoilers Abound)***

Housing Units

The place where prisoners call home

9. King Hedley II (King Hedley II [1999])

After a seven-year prison term, King Hedley II heads back into “the world” and seeks to reestablish himself. He bears a scar on his face from the scuffle that landed him behind bars, despite his protests saying that he killed the man who issued the defacement in self-defense. Now, King must deal with prospects of finding a way in life by hustling stolen refrigerators to finance a video store. He also must contend with a wonderfully independent wife, Tonya, who professes to abort King’s child. He opposes based on the belief that there will be a King Hedley III. It doesn’t matter though. In the end, King receives a bullet and after all of his time scheming and planning he dies never knowing if Tonya delivered the baby or not.

Sentence: Community service

A Different Kind of Fences

May these fences have gates that close

8. Troy Maxson (Fences [1985])

Disgruntled, befuddled, and confused, yet still engaging, witty, and strong, Troy Maxson from the play Fences is convicted of killing a man accidentally while engaged in a robbery. When he returns to life outside “the wall,” he is at times humorous and other times thoroughly bitter about his lot in life. Positioned to be a star negro baseball player like Jackie Robinson, Maxson never gets that break. He never names names but he believes that players like Josh Gibson could’ve gotten a better shot at Major League Baseball than Robinson. His ethics mixed, now honest at being a garbage man but who cheats on his wife, he somehow instills in his high school aged son the value of always making sure that someone is doing right by the young man in this life.

Sentence: Community service

The Barbs Are Unforgiving

Razor wire is proper for prisons

7. Harold Loomis (Joe Turner’s Come and Gone [1984])

Technically, Loomis is not a convict. He is kidnapped and forced to work on a chain gang. But the metaphor is too insightful to gloss over this character. Hunched over a kitchen table just like in Romare Bearden’s painting, Mill Hand’s Lunch Bucket (1978), Loomis has his song stolen from him. Out from underneath him for seven years, he is compelled to complete back-breaking, mind-numbing, soul-crushing labor for a man who illegally rounds up black men to fulfill his tasks. The significance of the song contains the notion that a man, every man and woman ought to have something to strive for, to live for in this world. Loomis finds some kind of song as he rips open his shirt, exposes his chest, and proceeds to slice it, saying, “I’m standing, now!” This shows a release from the doldrums that had him bound. Did he have to be a cutter to find his song, though?

Sentence: Fine of $1

The Wire is Real

There's no easy escape (as it should be)

6. Clarence “Booster” Becker (Jitney [1982])

In the play, Jitney, Booster has just returned from a twenty year prison stint for murder. The facts surrounding the case seem completely plausible. He kills a white woman who accuses him of a rape that he didn’t commit. He is sentenced to death row but his case is commuted, ultimately. After he is released from prison, he attempts to foster a better relationship with his father, Jim Becker. Because of his record, Becker is filled with anger and resentment towards a son that he senses ruined his whole life out of senseless vengeance. The two never reconcile as Becker dies on the job, leaving Booster to be the heir apparent to the jitney station.

Sentence: Two years of probation

The More Barbs the Better

A deterrent to say the least

 5. Sterling (Two Trains Running [1990])

The one thing that is constant with a string of characters that have just returned from the penitentiary in an August Wilson play is that there exists some redemptive quality in the individual. In Two Trains Running, Sterling is just discharged from prison for committing a bank robbery. He has within him a sense of what is right and wrong after being rehabilitated. All he wants is an opportunity. He finds it at Memphis Lee’s restaurant. What Wilson is showing in this instance is the fact that a man can change from whatever ogre he once was and fashion himself to be a model citizen.

Sentence: Two years of probation

The Dreaded Cells

Where the inmates inhabit

4. Sterling Johnson (Radio Golf [2005])

Not to be confused with Sterling from TTR, Sterling Johnson is a reformed inmate who served time for robbing a bank. Again, don’t confuse the two Sterlings or the two plays. In Johnson, a man of pragmatism exists. Though this may be a detriment, the fact that he is a self-made contractor for the people of Pittsburgh puts him in a category of a productive being. While it has been decades since his release from jail, Johnson still has to prove himself to be a man of character and promise. Wilson imbues in him a thought of how you can grasp that brass ring in America and hold it, even if you fell off of the carousel once.

Sentence: Five years of probation

This is Lockdown

You know that it's real when the cell door slams shut

3. Floyd “Schoolboy” Barton (Seven Guitars [1996])

In Seven Guitars Floyd “Schoolboy” Barton commits a much less heinous crime but a crime nonetheless: vagrancy. Throughout the play, stories are recounted regarding the life of this mythic figure. Toward the end, Schoolboy gets into a struggle with another character, Hedley. With a quick blow to the throat from a machete, Schoolboy expires. The scenes which follow do not make clear any arrests or anything, only suspicion by a character named Canewell. One can only suspect that Hedley will be found out and also spend time in the penitentiary for his crime.

Sentence for Schoolboy: Death

Sentence for Hedley: Life

The Infamous Cell

This where the reality sets in the most

2. Caesar Wilkes (Gem of the Ocean [2003])

Here, one would only have to suspect that Caesar kills Alfred “Solly Two Kings” Jackson by shooting him down like a dog in the street. In the aftermath, there is no talk about whether Caesar will face justice. But that is the essence of the Cycle. The wondering which takes place regarding what happens to these characters sketched so richly, after horrendous crimes like this occur is what is profound. 

Sentence: Life without parole

American Tales

The most moral country in the world also has the highest incarceration rate

1. Levee (Ma Rainey’s Black Bottom [1984])

All of the bluster and rage and anger that this character expresses could fill two plays. Mr. Wilson just chose one instead. But the trumpeter known as Levee, in Ma Rainey’s band exhibits the frustrations and misplaced hate over young black men in America. He tells a tale about how white men chastised and mocked a man of the clergy. This leads Levee to deliver a furious diatribe against the “white God” that other blacks are so enamored with, for what reason he knows not. Especially, he describes how his mother was raped by a pack of white men and that he bears the physical and psychic scars of the incident. While containing all of this pent of fury, he gets into a squabble with trombonist, Cutler. In the heated discussion which becomes a melee, Levee stabs Toledo, the piano player. The lights go dark and the curtains close. One can only assume that Levee will be tried for murder for his acts and destroy his entire future.

Sentence: Three life sentences to be served consecutively

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Why Are You Ranking: August Wilson’s Best Ex-Con, Could-Be-Criminals or Soon to Be Convicted Characters Listed From His ‘Twentieth Century Cycle’ of Plays
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