Want to win a Tony Award? Well, as with anything else in life, there are no guarantees – but if you play one of the roles featured in today’s Saturday List, your odds will improve considerably. Some characters are like magnets for Tony Awards and today we’re ranking the roles that have won two or more actors this most prestigious of theatre accoldates – just as the current Tony Awards season kicks into high gear. Let’s jump right in!

13. Marge MacDougall from Promises, Promises

Winning Tony Awards for Marian Mercer and Katie Finneran, Marge MacDougall in Promises, Promises is a fantastic supporting role for an actor with fabulous comedic timing and musical talents. At the top of the second act, leading man Chuck Baxter is drinking away his troubles at a bar on Christmas Eve, when he meets Marge, who is also tipsy and, like Chuck, a member of the Lonely Hearts Club. Together, in “A Fact Can Be a Beautiful Thing,” they decide that ‘Christmas (is) not the time to be alone with memories’ and to ‘throw a little joy’ each other’s way. They head off to Chuck’s apartment, which leads to a discovery that ignites the show’s second act. Marge is a character that actors love to play because of her wit, charm, and relatability. Quirky and endearing, she brings humour to the story and gives its heart a more layered perspective.

12. J. Pierrepont Finch from How to Succeed in Business Without Really Trying

While the second Broadway revival offered a host of younger actors like Daniel Radcliffe, Darren Criss and Nick Jonas in the central role of How to Succeed in Business Without Really Trying, it is the two older actors who played the role, Robert Morse and Matthew Broderick, in the first two Main Stem productions that walked away with a Tony Award for the role. The show details Finch’s ambitious journey as he climbs the corporate ladder at the World Wide Wicket Company, starting as a window washer and ending up as chairman of the board. En route, he sings a hilarious paean to himself, “I Believe in You” and leads the company in the show’s thrilling finale, “Brotherhood of Man.” There’s a fair deal for actors to do with the role, with Finch having to weigh up his choices against his moral compass, all the while keeping the audience on his side thanks to his wit and dynamism.

11. The Leading Player from Pippin

The Leading Player from Pippin is a role that has won awards in two different categories – Best Performance by a Leading Actor and Actress in a Musical respectively. Ben Vereen won his trophy when he originated the role, and Patina Miller followed in his footsteps when the show was revived. Complex and charismatic, The Leading Player is more than just the narrator of Pippin; Pippin himself is charmed and manipulated into his choices by this enigmatic and mysterious figure. The role is gifted with one of the great opening numbers in musical theatre, “Magic to Do,” so things start off iconic and build from there. The depth and ambiguity of the role make it a fascinating challenge for actors to portray, and the compelling results are ripe for recognition by critics and awards bodies alike.

10. Celie Harris-Johnson in The Color Purple

LaChanze wowed audiences as Celie in The Color Purple when the show first premiered on Broadway and when it was revived, Cynthia Erivo wowed them again. A host of other actresses have delivered impressive performances in this musical too, including Fantasia Barrino, who also played the role in the recent film adaptation of the show. With the whole show building up to Celie’s incredible climactic number, “I’m Here,” everyone leaves the show reflecting on the many challenges she has faced to get to this point in her life. Celie’s story is profoundly moving. It resonates deeply with us because of its universal themes of love, forgiveness, and the human spirit’s capacity to overcome hardship. Celie’s resilience, vulnerability, and ultimate triumph over adversity challenge actors to explore every emotional state under the sun, from pain and suffering to love and redemption. It’s a marathon.

9. Pseudolus from A Funny Thing Happened on the Way to the Forum

There are a lot of moving parts in A Funny Thing Happened on the Way to the Forum and at the centre of them all, is Pseudolus. From the moment Pseudolus leads the company in the rip-roaringly rambunctious opening number, “Comedy Tonight,” everyone knows they’re in for a good time. This role has won Tony Awards for Zero Mostel, Phil Silvers and Nathan Lane, each of whom brought their own brand of flair to the enslaved Roman whose heart is set on freedom and who will do just about anything to get it. This is a great role for an actor who is blessed with comedic genius, showcasing not only the skills of comic timing and improvisation, but also an ability to execute physical comedy as Pseudolus executes his fast-paced dialogue and the hilarious antics that get him in and out of the series of delightful complications that makes p the plot of this fast-paced show.

8. Carrie Pipperidge from Carousel

For this role’s award winners, it’s revivals all round! Audra McDonald won a Tony Award playing Carrie Pipperidge in the 1990s revival of Carousel, while Lindsay Mendez followed suit in the more recent one. Carrie is a great foil for leading lady Julie Jordan, who ends up in a difficult marriage with Billy Bigelow. While Carrie’s marriage to Enoch Snow (who we hear quite a bit about in “Mr Snow”) seems much happier and her story is played for comedy, Carrie’s entrapment in an upwardly mobile coupling has a few hidden challenges. For one thing, there’s not as much joy “When the Children Are Alseep” when there are nine of them! Even so, Carrie is a loveable and spunky character that allows actors to show off their vocal talents, comedic timing and even some emotional depth, with her genuine sincerity and unwavering loyalty making her someone that audiences adore.

7. Dolly Gallagher Levi from Hello, Dolly!

Two high profile actors, Carol Channing and Bette Midler have won Tony Awards playing Dolly Gallagher Levi, with so many others also having put their own stamp on this beloved matchmaker from New York, who finds love for herself and a number of the show’s other characters before the curtain ends and “Before the Parade Passes By!” (Pearl Baily, Etherl Merman, Betty White, Mary Martin, Bernadette Peters and Betty Buckley are just some of the divine divas who’ve played the role on Broadway or in productions around the USA and even the world!) Dolly’s larger-than-life personality, wit, and charm are all a part of the appeal for both the actors who play the role as well as the critics who review them – and that’s before you even get to the iconic musical numbers and show-stopping moments built around her. Once you’ve fallen on love with Dolly, there’s no saying “So Long, Dearie!”

6. Albin from La Cage aux Folles

George Hearn and Douglas Hodge both won Tony Awards for playing Albin, also known as Zaza, the star performer at a drag nightclub in Saint-Tropez. Life for Albin and his spouse, Georges, is thrown into chaos when Georges’s son announces his engagement to the daughter of the conservative deputy general of the Tradition, Family, and Morality Party. Albin’s journey involves embracing his true self while confronting societal prejudices and expectations. The role lets actors showcase their dramatic range and vocal talents, through several poignant scenes and powerful musical numbers, including “I Am What I Am,” “The Best of Times” and “A Little More Mascara.” The character’s combination of humour and humanity make it a standout role in musical theatre, earning accolades and recognition for actors who have delivered nuanced performances in the role.

5. Desiree Armfeldt from A Little Night Music

Desiree Armfeldt probably sings a little less than the average character on this list, but when everything you do on stage leads up to the incomparable “Send in the Clowns,” it goes without saying that it takes a masterful actor to play the part. As Desiree navigates the intricacies of love, desire and regret with poise and wit, with the end goal of winning back her lost love, Frederik Egerman, she has to be both captivating and vulnerable. Glynis Johns and Catherine Zeta-Jones both delivered the necessary complexity, sophistication and depth of emotion required by this role to nab the Tony Award – and Judi Dench did the same across the pond, winning the Oliver Award in a 1990s revival of the show. Desiree may be living “The Glamorous Life” as an actress in turn-of-the-century Sweden, but she might not have had the skill to play the role herself “Now,” “Soon,” or Later!”

4. Anna Leonowens from The King and I

Anna Leonowens in The King and I is a role that both actors and audiences are drawn to because of her strength and intelligence. She’s a pioneering woman who is ahead of her time, negotiating cultural differences and challenging social norms while maintaining her integrity and dignity. The character’s journey involves not only her interactions with the King of Siam, but also her own personal growth and transformation as she learns from and teaches those around her. Anna’s iconic songs, such as “Hello, Young Lovers” and “Shall We Dance,” provide actors like Gertrude Lawrence, Donna Murphy and Kelli O’Hara, all of whom won Tony Awards for their performances, with powerful moments to showcase their vocal and acting abilities. The role’s blend of wit, warmth, and resilience makes Anna both challenging and rewarding to portray.

3. Emile from South Pacific

Emile de Becque is a French plantation owner living on a South Pacific island during World War II. The character embodies a blend of strength, vulnerability, integrity and a whole lot of romantic appeal. His tender love for Nellie Forbush comes into conflict with the prejudices she holds about his past, specifically about his relationship with a Polynesian woman and their two children. Sadly as compelling and emotionally resonant a story today as it was in the 1940s, South Pacific leaves a lasting impact on audiences. Emile’s iconic songs, such as “Some Enchanted Evening” and “This Nearly Was Mine,” provide actors like Tony Award winners Ezio Pinza and Paulo Szot with powerful moments to showcase their vocal prowess and emotional depth. Portraying Emile requires a balance of sensitivity and strength and an actor can really layer their work as he steers his way through complex relationships and moral dilemmas.

2. The Emcee from Cabaret

The Emcee in Cabaret is a role that actors are drawn to because of its electrifying energy, dark allure, and complex character dynamics. The Emcee serves as the master of ceremonies at the Kit Kat Klub in Berlin during the rise of the Nazi regime, embodying the hedonism, decadence and moral decay of pre-war Germany. Actors who portray the Emcee need to bring to life a multifaceted character that blurs the lines between entertainer, provocateur and commentator on society. Unforgettable songs like “Willkommen,” “If You Could See Her” and (in the revivals) “I Don’t Care Much” balance a good deal of razzle dazzle alongside a chilling reminder of the looming political and social upheaval to come. Joel Grey won a Tony Award for Best Performance by a Featured Actor in a Musical ; in a theatrical twist of events, Alan Cumming would take home the Tony in the Leading Actor category.

1. Rose from Gypsy

Here she is, boys! Here she is, world! Here’s Rose! Rose in Gypsy is a possibly the greatest character in all of musical theatre, with layers of complexity that actors relish portraying. She undergoes a profound transformation throughout the story, evolving from a determined stage mother to a woman grappling with her ambitions, regrets and sense of identity. Angela Lansbury, Tyne Daly and Patti LuPone all won Tony Awards as they explored the character’s wide range of emotions, her fierce determination and relentless drive as well as her vulnerability and heartache. Additionally, Rose’s iconic musical numbers, such as “Some People,” “Everything’s Coming Up Roses” and “Rose’s Turn,” first introduced on stage by Ethel Merman, give Rose a dynamic character arc and an emotional depth second to none.

Final Thoughts

As the 77th Tony Awards draw near, two additional roles stand a chance of joining these characters in as multiple Tony Award winners. Both are from Cabaret: Sally Bowles, played by Gayle Rankin, and Herr Schultz, played by Steven Skybell. Moreover, the Emcee could rise up in the ranks if Eddie Redmayne takes home the prize for his work in the role. I’m rooting for Kelli O’Hara, Daniel Radcliffe and Jonathan Groff in those categories though. Whoever you’re rooting for, let’s keep celebrating the incredible talent and artistry showcased on Broadway stages as well as those closer to home. Whether it’s the dazzling performances of leading actors or the show-stopping turns of supporting players you love, each of the award-winning roles we’ve ranked today represents a shining moment in the history of musical theatre. Here’s to the magic of musicals and all of the unforgettable performances yet to come!