Darian Dauchan, a solo performance artist from New York, knows how to make a strong first impression.

In fact, his entire play “Entertainer’s Eulogy,” now running at TheatreWorks as part of Playhouse on the Square’s Solo Works series, is about impressions.

In "Entertainer's Eulogy" at TheatreWorks, New York writer and actor Darian Dauchan portrays a minstrel performer, a soul singer and a boxer to show the evolution of the black entertainer in America.

Darian Dauchan

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But the first one is a doozy: He enters in a top hat and a wide grin and performs a soft shoe dance for pennies.

There’s no doubt that African-American entertainers in the 20th Century have faced obstacles that white performers could never imagine, from racism to exploitation. There’s also no doubt that some problems are brought upon the performers themselves, like drug addictions and anger issues. Dauchan’s examination of three such entertainers variously shows the pitfalls and pratfalls that have destroyed so many rising black stars.

First, Dauchan introduces Roscoe Lee Thorton, a minstrel dancer who gets plucked off the street by a producer to be in a blackface vaudeville act. Roscoe’s smiling, aim-to-please on-stage persona is no different off-stage. He doesn’t realize he’s being exploited, or that he is becoming a parody of himself.

Next is Lonnie Davis, a soul singer in the 1960s whose antics get him pushed out of a church choir and into a record deal. With the charismatic personality of an Al Green or a Johnnie Taylor, he writhes on the floor singing “I’ll Make Sweet Love to You!” But his taste for women and drugs is as potent as his talent.

Finally, Dauchan appears as Theo “The Chef” Johnson, an upstart middleweight boxer with the bravado of Muhammad Ali and the temper of Mike Tyson. He can knock out a man in one round, but out of the ring, he becomes unstable in the face of high expectations.

Dauchan tells each character’s story in chapters, one at a time. He’s a tall, expressive actor with the rapid-fire delivery of a slam poet. His play never loses energy, and scene changes are helped along with video projections by Desha Dauchan. The short films reveal the characters as they appear in the media: the boxer is selling Wheaties cereal, the minstrel is playing the fool in a silent film, and the soul singer is acting cool in an interview.

The audience aches for these tragic personalities, wishing they could see themselves as we see them. In one of the play’s most heartbreaking moments, Roscoe hold up a blackface doll that has been made of him. He’s happy to have a toy with his name on it, but he also observes: “It doesn’t look anything like me… I can’t quite explain it, but it hurts.”