Milwaukee Chamber Theatre’s ‘Topdog/Underdog’ a Contemporary Classic

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Photo by Michael Brosilow

Topdog/Underdog - Milwaukee Rep

Milwaukee Repertory Theater presents 'Topdog/Underdog' at Broadway Theatre Center’s Studio Theatre through May 11, 2025. Pictured (left to right): Anthony Fleming III and Dimonte Henning.

Dreams and visions carve themselves into the shadows of the American consciousness in Milwaukee Chamber Theatre’s production of Topdog/Underdog. The deep thematic complexity of playwright Suzan-Lori Parks’ contemporary classic resonates through the studio theatre as Anthony Fleming III and Dimonte Henning restlessly shuffle around the stage in the roles of a couple of brothers named Lincoln and Booth.

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Photo by Michael Brosilow

Anthony Fleming III in Topdog/Underdog - Milwaukee Rep

Milwaukee Repertory Theater presents 'Topdog/Underdog' at the Broadway Theatre Center’s Studio Theatre through May 11, 2025. Pictured: Anthony Fleming III.

The inner complexities of Parks’ script find an impressive array of articulation throughout the production. It’s just two guys talking about work and hustle needed to scratch a life out of poverty. Risk and reward rumble through the squalor of urban poverty between two brothers. Fleming and Henning conjure distinctly dangerous moods, motions and emotions as they hover around the edge of disaster. Fleming has a deeply resonant presence onstage that wields a heavy gravity through the tensions he engages in with Henning. Henning carries a scrappy energy about him that pairs well with the somber intensity of Fleming’s energy as Lincoln—a man with a legitimate job of getting shot in a Lincoln costume by tourists in an arcade.

The challenge for any two-person drama is to modulate well around the edges of the drama while holding an audience’s attention in the central conflict. Parks’ script makes this particularly difficult as it’s a bit of a marathon. Two and a half hours of restless desperation would be difficult for anyone to manage, but Henning and Fleming manage the intimidate fluctuations of dramatic energy needed to maintain a healthy heartbeat at the center of the drama. From silent moments of guarded tension to explosive moments of erupting emotion, Henning and Fleming manage a very tight rapport that can be positively breathtaking in places.

Milwaukee Chamber Theatre’s production of Topdog/Underdog runs through May 11 at the Broadway Theatre Center’s Studio Theatre. For ticket reservations and more, visit Milwaukee Chamber Theatre online.