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Sublime ‘How I Learned What I Learned’ delves into life lessons that shaped August Wilson the writer and his works

At a brisk 90 minutes, “How I learned What I Learned” is decidedly August Wilson’s shortest play by a solid hour. It’s also his most overtly personal.

Across the 100 years and 10 dramas that encompass Wilson’s Century Cycle (one play for each decade in the 20th century), the playwright mined his own memories in creating deeply memorable characters primarily living (and sometimes dying) in Pittsburgh’s Pill Hill Neighborhood.

“How I Learned” was published in 2003, and marked a departure for the two-time Tony and Pulitzer winner. The stories Wilson relays here aren’t woven into the structure of a traditional drama and aren’t restricted to a single decade. Running through May 5, the one-man show and co-production between Congo Square Theatre (a company Wilson supported mightily) and Broadway in Chicago stars Harry Lennix (“Blacklist,” “Chi-Raq,” “Man of Steel” ) as Wilson, relaying a series of vivid anecdotes that span the playwright’s life from his childhood to his years as an emerging writer navigating the world of Pittsburgh and beyond.

Directed by Ken Matt-Martin, “How I Learned” is essential viewing for Wilson fans. It also stands on its own as a compelling tale of a Black artist grappling with often formidable trials and tribulations of everyday life in these United States. As Lennix unspools a series of stories that range from violent to celebratory, Wilson becomes the central character in his own story and it’s a story worth hearing.

‘How I Learned What I Learned’

Wilson’s script starts with a self-evident truth. His ancestors, Lennix-as-Wilson notes shortly after the lights come up, have been in this country since the mid-17th century. Until 1863, he adds, they never had a problem finding a job.

He also explains why he’s wearing a T-shirt emblazoned with the pronouncement “I Am Supposed to Be White.” He bought it online from a man named Clarence Thomas, he notes. The shirt is a jumping off point for a rudimentary lesson in the way racism was baked into the official Webster dictionary definitions of “black” and “white.” The former’s meanings: “wicked, dishonorable, connected with the devil, menacing, sullen, hostile, unqualified, and affected by an undesirable condition” — are projected on the massive typewriter set designer Sydney Lynne Thomas has framing the stage.

Those early moments set the tone for a monologue penned by a true raconteur. Throughout, “How I Learned” balances wry truths on a knife edge between tragedy and comedy.

As a youth, Wilson knew his family wasn’t welcome in Pill Hill, also known, he explains as “an amalgam of the unwanted.” If the brick through their new home’s window didn’t make it clear, the church did. When the Monsignor of young Wilson’s Catholic parish announced Blacks would be welcome and anyone who didn’t like that could leave, all but three parishioners departed. The weekly collection plate went from roughly $2,000 to just over $100. The Monsignor was fired.

When his mother won a new washing machine from a local radio station, the prize was downgraded to a coupon for the Goodwill shop after the organizers realized she was Black. She refused to collect, saving for a year to buy her own new machine, and leaving Wilson with words to live by: “Something is not always better than nothing.”

That lesson plays out through Wilson’s numerous, demeaning pre-playwright jobs. Hired to shelve toys at a local store, he walks out the first day, after the owner threatens to shoot him if he’s caught stealing. He quickly finds work cutting grass but leaves that job when his employer tells his to step aside after a client yells that they don’t want a Black man on their lawn.

“How I Learned” doesn’t move in chronological order, but that doesn’t matter. Listening to Lennix is like being at a dinner party with Wilson — the playwright enthralling everyone gathered with tales that capture significant aspects of his life, and (literally) speak to the magnificent dramas he penned for the stage.

Throughout, Wilson takes moments that are enraging and uses them to highlight his own fortitude, intelligence and keen sense of humor. Approached at a gathering by a white man who insists he didn’t see color, Wilson pointedly asks why the white man had decided to explain that to the only Black man in the room.

Lennix wears Wilson’s persona — and signature newsboy cap — with ease and grace. As he weaves together anecdotes from the playwright’s eventful life, the audience gets a direct look at the power within the man behind the pen.