Cannavale made his professional stage debut in a 1998 production of The Most Fabulous Story Ever Told at the Williamstown Theatre Festival in Massachusetts, a prestigious launchpad for many shows and stars that go on to Broadway. Paul Rudnick's play reimagines the biblical creation story, following Adam, Steve (Cannavale's role), and their lesbian friends from the Garden of Eden and through the centuries.

Talk about making your Off-Broadway debut with a bang. Cannavale's came with The Public Theater's 2003 production of Fucking A, a Scarlet Letter-inspired drama by Pulitzer Prize winner Suzan-Lori Parks. Cannavale played the nameless Mayor, who deserves his own A for adultery.

In 2005, Cannavale returned off Broadway in a Drama Desk Award-nominated revival of David Rabe's 1984 ensemble play Hurlyburly, about Hollywood players searching for meaning in their lives. Among a cast that also included Ethan Hawke, Wallace Shawn, Parker Posey, and more, Cannavale was singled out with praise for his performance.

"Cannavale delivers the play’s closest approximation of pathos in his funny, volatile perf," a Variety review reads. "Cannavale makes bewildered Phil, despite his brutality, the only character whose anguish is palpable and transparent."

Cannavale finally put his stamp on Broadway in 2007, starring as the mysterious Dennis in Theresa Rebeck's Mauritius. The play follows two sisters with a valuable stamp collection and the three men, including Dennis, who covet it. Cannavale brought "captivating vitality and charm" to his performance, per The New York Times, and earned his first Tony Award nomination in 2008.

Cannavale followed up his Broadway debut with another Tony-nominated performance, starring as Jackie, a fresh-from-prison dealer as troubled with drugs as with love, in Stephen Adly Guirgis's high-octane drama. He won the Drama Desk Award and, collectively with the five-person cast, the Lunt-Fontanne Award for Ensemble Excellence at the Theatre World Awards.

Cannavale played Broadway's Gerald Schoenfeld Theatre twice in quick succession: first in The Motherfucker with the Hat in 2011, and then in David Mamet's Pulitzer Prize-winning classic Glengarry Glen Ross in 2012. As ruthless, top-selling real estate agent Richard Roma, he starred alongside Al Pacino, David Harbour, and his future Here We Are co-star Jeremy Shamos.

Earlier in 2012, Cannavale made his only musical Broadway appearance with the one-night benefit concert Barack on Broadway, a fundraiser for Obama's reelection campaign.

Mining similar themes as in Hurlyburly, Cannavale starred in a 2013 revival of Clifford Odets' The Big Knife on Broadway, a play inspired by Odets's own disillusionment with the Hollywood system after working there for six years. The starry cast also included Rachel Brosnahan, Richard Kind, Marin Ireland, and Chip Zien.

Nassim Soleimanpour's solo play about censorship and oppression, written while barred from leaving his native Iran, is perhaps one of the most unique theatre pieces an actor can take on. There's no set, director, or rehearsals, and the actor — a different one at each performance — has never seen the script before. Cannavale was among the lineup of its 2016 Off-Broadway run at the Westside Theatre.

In the Broadway adaptation of the same-named (mostly) nonfiction book, Cannavale starred as essayist John D'Agata, who plays fast and loose with facts in the name of a good story. Going toe-to-toe with Cherry Jones (as a magazine editor) and Daniel Radcliffe (as a fact-checker), Cannavale was "ferociously talented," per Variety's critic.

One of the buzziest events of the 2023-24 theatre season wasn't on Broadway. It was the Off-Broadway world premiere of Here We Are, the final, unfinished musical Stephen Sondheim was working on before his 2021 death. Adapted from Luis Buñuel's films The Discreet Charm of the Bourgeoisie and The Exterminating Angel, the show featured Cannavale as Leo Brink, one half of a posh couple whose home is the starting point for an eclectic ensemble's surreal adventures.

The star-studded "dream cast," as New York Theatre Guide's critic described it, also included Tracie Bennett, Denis O'Hare, Steven Pasquale, Amber Gray, Jeremy Shamos, Rachel Bay Jones, Francois Battiste, Micaela Diamond, Jin Ha, and David Hyde Pierce.

Bobby Cannavale's theatre career proves he knows a thing or two about good art, and he puts that knowledge on display in Yasmina Reza's Tony Award-winning play. When Marc's friend, Serge (Neil Patrick Harris), buys a plain white painting for a small fortune, Marc's criticisms ignite a debate that jeopardize the longtime friendship between Marc, Serge, and Yvan (James Corden).

You'll have to make your own appraisal of the play, but this trio's talent is of guaranteed value.

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