August Wilson’s Two Trains Running takes place in 1969 in the working-class Hill District of Pittsburgh, Pennsylvania. Now on at American Conservatory Theater, it’s part of Wilson’s famous “Pittsburgh Cycle,” his series of ten plays that depict African-American life across different decades. His best-known work, Fences, portrayed the 1950s and premiered on stage in 1985 before becoming a 2016 film starring Denzel Washington and Viola Davis.
James Milord and DeAnna Supplee
Stories about working-class communities often center around a neighborhood gathering place — a barbershop, a beauty salon, a local bar. A place, as the famous Cheers tagline put it, “where everyone knows your name.” In Two Trains Running, that place is a humble diner in the Hill District, and it has its own lively cast of characters.
Michael A. Shepperd, Robert Cornelius, and Brian D. Coats
Memphis Lee (Michael A. Shepperd) is the longtime owner, trying to hold out for a fair price as urban renewal creeps closer. He knows the diner’s days are numbered, but he’s determined not to get shortchanged. Risa (Deanna Supplee, alternating with Diana Coates) is the lone waitress — guarded, attractive, and fiercely independent. She keeps the men, and any suitors, at a careful distance.
J'Laney Allen and Michael A. Shepperd
The regulars are a vivid bunch: Holloway (Michael J. Asberry) is the older, wiser voice of the community, a man who’s seen it all. Wolf (J’Laney Allen) is the slick neighborhood bookie, always chasing the next big score. Hambone (Chuck Benson), mentally challenged — perhaps what we’d now recognize as being on the autism spectrum — repeats his own story of injustice like a daily prayer, while Risa watches out for him. West (Robert Cornelius), the neighborhood mortician and a rare success story, keeps trying to buy Memphis out. And then there’s Sterling (James Ricardo Milford), freshly out of prison — young, restless, full of dreams about changing the world, though his work ethic may not always match his ambition.
J'Laney Allen and James Milord
Chuckie Benson, Michael A. Shepperd, and Diana Coates
The world along with the old neighborhood is changing. For the African-American community in 1969, The Civil Rights Movement is in full swing, and things in the community are shifting. But who is benefitting and who is being left behind? Despite everyone’s bravado about future plans of prosperity, there is fear in their hearts. There are many heated conversations in the diner about the past versus the future ahead. Were things better before or is a new day dawning? Nothing is definite. The scenes in both acts build on each other as the conversations get deeper. As tensions rise, reality checks come hard and fast, shifting the dynamic inside the diner. Wilson’s dialogue captures the uncertainty of the time with a rigorous, poetic honesty and humor.
Brian D. Coats, Michael A. Shepperd, James Milord, and Chuckie Benson
The meaning of the title Two Trains Running is left up for interpretation: maybe it’s hope versus despair, or past versus future. Either way, the sense of movement — and uncertainty — runs through the entire play.
Tanya Orellana’s exquisitely detailed set has worn linoleum floors, booths, and counter seating — it’s so authentic you can almost smell the coffee burning in the pot and hear the bacon sizzling in the kitchen. The diner feels real enough to step into, a reminder of a time when every neighborhood had its own “greasy spoon.”
Michael A. Shepperd and Robert Cornelius
With backstories to help us flesh them out, every character feels familiar — not because they’re clichés, but because they’re fully realized people trying to survive, to dream, and to belong. The acting across the board is strong; worth mentioning is Shepperd a force as Memphis, whether leading a debate about race and justice or just holding his own in the background; he’s bound and determined to come out on top, no matter what lies ahead. Milford’s captivating Sterling brings a fiery unpredictable idealism and youthful energy to the room — is he foolish, brave, or both? Maybe he’s just there as comic relief. His character keeps everyone guessing.
James Milord, Brian D. Coats, and J'Laney Allen
The two-and-a-half-hour runtime is daunting, yet director Lili-Anne Brown keeps the story moving in The Acting Company’s production. Yes, Wilson’s writing gives every character their own point of view, but Brown makes sure we hear each voice clearly.
The questions Wilson poses in Two Trains Running have no simple answers. Hope is fragile. Change is inevitable. But no matter what, you find yourself rooting for every last person in that diner — even knowing that a happy ending isn’t guaranteed.
photos by Lore Photography
Two Trains Running
American Conservatory Theatre
The Acting Company, in partnership with Play On Shakespeare
A.C.T.’s Toni Rembe Theater, 415 Geary St.
2 hours and 30 minutes with one intermission
ends on May 4, 2025
for tickets, call 415.749.2228 or visit A.C.T.
playing in rep with Shakespeare’s The Comedy of Errors, which ends on May 3
