Broadway’s Surefire Paths to a Tony Award: Iconic Roles That Keep on Giving

Each Broadway season, familiar names surface among the Tony Award nominations. These aren’t just famous performers, but legendary roles that, time after time, serve as stepping stones to Broadway’s most prestigious accolade. Whether it’s Herbie in Gypsy, Shelley Levene in Glengarry Glen Ross, or Norma Desmond and Joe Gillis in Sunset Blvd., some characters seem almost guaranteed to earn a nod from the Tony nominating committee. Yet, securing that nod means much more than stepping into a known character; actors must craft their own compelling interpretation.

Danny Burstein, nominated for his role as Herbie in this season’s revival of Gypsy, entered rehearsals with a keen awareness of the legacy behind him. Having personally worked with previous Herbies—Jack Klugman, Jonathan Hadary, John Dossett, and Boyd Gaines, all former Tony nominees—Burstein carried their influence while developing his portrayal. Rather than fearing comparison, Burstein embraced this lineage, crafting a Herbie who stands more assertively against the powerful Mama Rose, portrayed by fellow nominee Audra McDonald.

Indeed, Gypsy illustrates just how frequently classic roles can translate into Tony gold. Every Broadway incarnation of the show has earned Tony nominations for the three central roles: Mama Rose, Herbie, and Louise. McDonald’s nomination follows in the footsteps of Broadway greats Ethel Merman, Angela Lansbury, Tyne Daly, Bernadette Peters, and Patti LuPone, highlighting just how reliably rewarding some roles can be.

But this phenomenon extends far beyond Gypsy. Consider the enduring appeal of Edward Albee’s Who’s Afraid of Virginia Woolf?—Arthur Hill, Bill Irwin, and Tracy Letts each secured Tonys for portraying George. Likewise, performers playing the Emcee, Sally Bowles, and others in Cabaret regularly earn nods. Stephen Sondheim’s Sweeney Todd has reliably delivered nominations for every actor playing its iconic leads, demonstrating the allure and prestige these roles carry.

Yet, it’s not simply the iconic nature of these parts that ensures Tony attention. This season’s revival of Glengarry Glen Ross illustrates that point clearly. Bob Odenkirk secured his nomination for Shelley Levene, a role previously celebrated through Tony nominations for Robert Prosky and Alan Alda. However, his co-star Kieran Culkin, portraying Richard Roma—an equally award-rich role historically—was overlooked, emphasizing that prestige alone isn’t enough; the actor must also deliver something uniquely compelling.

Odenkirk’s success stems from his intentional divergence from earlier portrayals, most notably Jack Lemmon’s iconic film performance. Rather than playing Shelley as entirely defeated, Odenkirk presents a man clinging fiercely to hope, adding fresh urgency and distinctiveness to a well-trodden role.

Similarly, the acclaimed revival of Sunset Blvd. provides a noteworthy case. Tom Francis, nominated alongside Nicole Scherzinger, tackled the role of Joe Gillis without ever referencing previous performances by William Holden or Alan Campbell. His fresh, unburdened perspective allowed him to infuse originality into his portrayal, earning critical acclaim and a Tony nod.

Actors often approach these legendary roles mindful of their predecessors yet determined to craft interpretations that resonate personally and authentically. Iconic characters offer rich canvases, yet it remains the actor’s job to deliver performances that feel both fresh and deeply genuine.

So, while stepping into these classic roles might increase an actor’s chance of Tony recognition, it also presents the daunting task of living up to—and transcending—the performances that came before. The actors who succeed manage to balance homage with originality, proving yet again that Broadway’s most timeless roles continue to offer fertile ground for artistic triumph and Tony gold.

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