In Love and War: Jiréh Breon Holder’s Too Heavy for Your Pocket Weighs the Price of Freedom

Ayanna Bria Bakari as Evelyn Brandon (top) and Jalen Gilbert as Bowzie Brandon
Photo: Kenny Nakai (TimeLine Theatre Company)

It’s funny how the more things change, the more they say the same. Friday, May 17, marked 65 years to the day of the Brown v. the Board of Education ruling—a bittersweet anniversary, as civil and human rights continue to be rolled back across America and deep inequities for black and brown people persist with no foreseeable end in sight.

It was also a particularly poignant date to watch a performance of Jiréh Breon Holder’s civil rights drama, Too Heavy for Your Pocket, now in production at Chicago’s Timeline Theatre, directed by Ron OJ Parson. Part love quadrangle, part coming-of-age story and part history lesson, the ensemble drama focuses on two deeply interconnected young couples in civil rights era Tennessee reckoning with the limitations of race, gender, class, love and ultimately, freedom.

Jalen Gilbert as Bowzie Brandon
Photo: Lara Goetsch (TimeLine Theatre Company)

It’s 1961 in Nashville, and local young marrieds Sally Mae and Tony Carter (Jennifer Latimore and Cage Sebastian Pierre) and Bowzie and Evelyn Brandon (Jalen Gilbert and Ayanna Bria Bakari) share an enviable bond. Despite financial challenges, emotional immaturity and the looming shadow of segregation, the camaraderie and respective romances of these superbly-acted characters evoke the best of black culture—namely, our profound love for each other and ability to laugh, even in the worst of times.


But when Bowzie abandons his scholarship at nearby Fisk University—and to some extent, Evelyn—to become a Freedom Rider, his departure triggers a devastating series of revelations. In his absence, the remaining three members of this quartet are, in a word, lost—as is Bowzie, himself.

Playwright Holder was reportedly inspired to write Too Heavy for Your Pocket in response to somewhat glossy historical narratives such as The Help, which recalled the battle for civil rights without centering those most deeply affected. Embarking on his own historical research, an anecdote from his grandmother inspired the Morehouse and Yale graduate to write the story of a man who sacrifices everything for the fight for freedom, and how it affects those closest to him. The story closely echoed that of director Parson’s own cousin, Jerry Moore, who left college to board one of those history-making buses. Parson dedicated the production to him, writing, “I knew his spirit would guide me through this journey.”

TimeLine Theatre Company/YouTube

But to simply call Too Heavy for Your Pocket a civil rights drama would be reductive. While the era provides the context, each of these characters is fighting for freedom in their own way, betraying and damaging each other in the process. Of note is Gilbert’s treatment of his female characters. The relationship between Sally Mae and Evelyn speaks to the best and worst within us, and Holder doesn’t shy away from exploring how black men’s liberation often comes at the expense of the black women who love them.


“A Negro woman will follow Satan to grave,” Evelyn rages at one point, “as long as he’s dressed like a black man.”

As Sally Mae, who frequently serves as the quartet’s moral compass, Jennifer Latimore gives a deeply nuanced and gripping performance, in many ways echoing the deep turmoil behind the polite smiles and careful manners of blacks during segregation (and many might argue, beyond). Evelyn (Ayanna Bria Bakari) and Tony (Cage Sebastian Pierre) wear their anguish closer to the surface, while Bowzie’s quiet yet destructive frustration is excellently conveyed by Jalen Gilbert. Together, they comprise an incredibly powerful quartet; the emotional output almost overwhelming in its impact.

Clockwise from left: Ayanna Bria Bakari (Evelyn Brandon), Jalen Gilbert (Bowzie Brandon), Cage Sebastian Pierre (Tony Carter), and Jennifer Latimore (Sally Mae Carter)
Photo: Kenny Nakai (TimeLine Theatre Company)

Breath is a recurrent motif in Too Heavy for Your Pocket, and audiences may occasionally need to catch theirs, as the often painfully relatable growing pains of these characters come in quick succession. For this writer, also impossible to ignore was the correlation between these characters’ struggle for breath and the words “I can’t breathe,” spoken by police chokehold victim Eric Garner and subsequently adopted by those leading our current struggle for civil rights. As Bowzie dreams of a world in which his unborn children can live free of abuse and police harassment because of his immense sacrifice, it was a painful reminder that, in the words of Nina Simone’s 1961 hit “Work Song,” we still have so very far to go.


Too Heavy for Your Pocket is in production through June 29 at the TimeLine Theatre in Chicago. You can purchase tickets here.

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Maiysha Kai

Maiysha Kai is Managing Editor of The Glow Up and your average Grammy-nominated goddess next door. Minneapolis born, Chicago bred, New York built. Nuance is her superpower.