The Shocking Underdog Victory
Sometimes, a play comes along that seems to defy all expectations. In 2013, the race for Best Play included heavy hitters like Nora Ephron's final play, "Lucky Guy," starring Tom Hanks. Yet the award went to Christopher Durang's Chekhov-inspired comedy,
"Vanya and Sonia and Masha and Spike." While a critical favorite, its victory was seen as a surprise against more commercially prominent competitors. The play, starring Sigourney Weaver and David Hyde Pierce, was a witty, heartfelt piece about sibling absurdity that captured the voters' imaginations. It proved that a well-crafted comedy, even one filled with absurdism and references to ancient Greek drama, could triumph over star power and more traditional dramatic fare, leaving an indelible mark on the season.
When the Zeitgeist Demands a Different Winner
Awards often reflect the cultural moment, and no race demonstrated this more clearly than the 2019 contest. Jez Butterworth's "The Ferryman" was a massive, critically acclaimed production—a sprawling Irish drama with a huge cast and magnificent staging. It was the safe bet. Its competition was Heidi Schreck's "What the Constitution Means to Me," a deeply personal, semi-autobiographical piece that felt more like a town hall than a traditional play. "Constitution" explored themes of women's rights, domestic abuse, and the very fabric of American law in a way that felt incredibly urgent. While "The Ferryman" ultimately took home the Tony, the debate surrounding the two plays was fierce. Many critics argued that "Constitution," with its raw, direct engagement with the political climate, was the more vital and important work of the year, even if it didn't fit the classic mold of a Best Play winner.
The Play That Was Too Controversial
There are times when a play is so groundbreaking and challenging that it rattles the establishment. Edward Albee's "Who's Afraid of Virginia Woolf?" is now considered a masterpiece of the American stage. In 1963, it did win the Tony Award for Best Play. However, its journey was fraught with controversy. The play's searing portrayal of marital strife, along with its profanity and sexual themes, was shocking to some audiences and critics at the time. The play had been recommended for the 1963 Pulitzer Prize for Drama, but the advisory board overruled the jury, citing its themes as not being "wholesome." No prize for drama was awarded that year in protest. The Tony win, in this context, was a major validation, but the Pulitzer snub shows how close the play came to being officially dismissed by the cultural gatekeepers of its era.
The Record-Breaking Snub
Sometimes, the story isn't an upset win but an astonishing loss. Jeremy O. Harris's "Slave Play" arrived on Broadway as a cultural phenomenon. It was provocative, incisive, and sparked intense conversation. The play earned a record-breaking 12 Tony nominations, the most ever for a non-musical play. It was widely projected to win Best Play. Instead, it walked away with zero awards. The top prize went to "The Inheritance," a sweeping epic about gay life in the 21st century. The complete shut-out of "Slave Play" was one of the biggest surprises of the night, leaving many to wonder if its confrontational style and challenging themes were ultimately too much for Tony voters. It became a historic example of a show that dominated the conversation but couldn't translate that buzz into hardware.












