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VOICE OVER: Emily Brayton WRITTEN BY: Joe Shetina
It's not over until the talented lady sings! Welcome to MsMojo, and today we're counting down our picks for the most technically difficult female roles to sing and perform, often played by some of the biggest stars of the stage. Our countdown includes roles in musicals “Anything Goes”, “Caroline, or Change”, “Miss Saigon” and more!

Welcome to MsMojo, and today we’re counting down our picks for the most technically difficult female roles to sing and perform, often played by some of the biggest stars of the stage. What do you think is the hardest role on this list? Tell us in the comments.

#30: Fosca

“Passion”
In this lesser-known Stephen Sondheim musical, Fosca is a chronically ill and profoundly sad woman living in her own fantasies. She falls desperately in love with a soldier, Giorgio. Her love for him is so deep and fierce that it threatens to destroy them both. It takes profound power and presence as a performer to sell Fosca’s longing without coming off as ridiculous. When played well, it’s shattering. The role has been taken on by stars like Maria Friedman, Judy Kuhn, and Patti LuPone. Donna Murphy won a Tony for the 1994 production.

#29: The Lady of the Lake

“Spamalot”
Sara Ramirez made it look effortless, but that’s what made their Tony-winning performance as the Lady of the Lake such a miracle. “Spamalot” turns the mythical enchantress of Arthurian legend into a high-maintenance diva. True to form, she gets some of the showiest and most challenging numbers. To the character’s great disappointment, she gets a bit sidelined in the second act. But she still gets one of the most belt-heavy solos in modern musicals on her way out. To sell this role, you have to have truly legendary vocal and comedic chops. Luckily, performers like Ramirez and Hannah Waddingham have been up to the task.

#28: Trina

“Falsettos”
“I’m Breaking Down” is a classic comedy number. But it’s also a trap! The song encompasses everything that’s so hard to get right about Trina. She is one or two exaggerated gestures from being a complete caricature of a woman wronged by a man. A performer who can’t balance motivated comedy with actual humanity could turn a great and complex character into a one-note joke. As any heartbroken fan can tell you, “Falsettos” becomes a lot less funny in its second act. Trina follows suit, meaning the actor also has to sell some more dramatic and poignant moments before the curtain goes down.

#27: Cassie

“A Chorus Line”
The entire ensemble of this dance-based musical is full of broken dreams and being spitting distance from stardom. Cassie is the character closest to being a real star. She’s talented, charismatic, and respected. Yet she’s still at this audition for a chorus part. But even if she can’t be a star in her own right, she lives to dance. Her defiant and passionate solo, “The Music and the Mirror,” is one of the show’s most notable moments. Everyone in the cast has to dance, but this moment requires an actor who can sell the emotion of a scene with her words, voice, and body.

#26: The Witch

“Into the Woods”
If you want murky morality, look no further than any Stephen Sondheim musical. But the lynchpin character of “Into the Woods” is a tall order. Bernadette Peters originated the role on Broadway and set the standard for the character’s tight punchlines and resonant numbers about everything from parenting to vegetables. Masterful technique is a requirement. The score is constantly keeping the performer on her toes with beautiful melodies, shifting tempos, and even a rap about her prized garden. More than that, though, the actor playing the Witch has to be able to oscillate between the character’s villainy and vulnerability.

#25: Audrey

“Little Shop of Horrors”
What musical theater ingénue doesn’t secretly think she can do Audrey? Two things work against anyone trying to make this character their own. One, it’s a delicate balance between making her funny and making her a joke. She’s a clear take on a particular platinum blonde archetype, but she’s also wise and empathetic. The second challenge is that original Off-Broadway actress, Ellen Greene, put such a strong stamp on the role that anyone who takes it on is almost sure to fall short. Her accent and phrasing have almost become synonymous with Audrey. If you’re gonna play her, you need to have an original take.

#24: Daisy & Violet Hilton

“Side Show”
Technically, this is two roles, but if it’s good enough for the Tonys, it’s good enough for us. Alice Ripley and Emily Skinner shared a joint nomination for originating the roles of Daisy and Violet Hilton in “Side Show.” Based on the lives of two real conjoined twins who were featured in vaudeville shows in the 1930s, the actors’ costumes are fused together, requiring them to move as one. This is a challenge that forces performers to completely change the way they’re used to moving on stage. That’s to say nothing of the soaring vocals and harmonies they’re meant to perform.

#23: Amy

“Company”
Other than its lead character, the chronically unmarried Bobby, most of the characters who appear in “Company” are in it for a good time, not a long time. One of the show’s most famous numbers is “Getting Married Today,” a tongue-twisting, oxygen-defying song sung by Amy. It’s her wedding day, and her anxiety about being a married woman reaches a fever pitch. There’s hardly any space to breathe. It’s a good thing Amy’s performer is offstage for most of the show — she probably needs time to prepare. And she probably needs the rest of the show to recover.

#22: Maria

“The Sound of Music”
Considering the legendary status of the actresses who played her, Maria is a deceptively difficult role. Mary Martin on Broadway and Julie Andrews on film make it look easy. But it takes a lot of effort to play the novice nun in Rodgers and Hammerstein’s “The Sound of Music.” That’s true even before you consider how hard it is to sing the role. Maria requires a performer to have a clarity of pitch and tone that’s not easily earned or kept. It also tasks her with playing the character’s inherent goodness without coming off as too corny or naïve.

#21: Ti Moune

“Once on This Island”
Adapted as a retelling of “The Little Mermaid” and set in the Antilles, “Once on This Island” tells the story of Ti Moune, a peasant girl of local myth. She becomes enamored with a rich man and gets caught up in the complicated racial and class dynamics at play on the island. Oh, and there’s also a bet between four powerful gods. When playing Ti Moune, a performer has to carry herself with ethereal grace, yet still be believable as a fragile and wide-eyed young woman. The musical puts her through the wringer, and it takes an actor who can tap into an inner strength to really pull it off.

#20: Angelica Schuyler

“Hamilton”
The Schuyler Sisters are a wonderful trio, and while Alexander’s wife Eliza has emotionally taxing and difficult songs like “Burn”, her sister has some as well and requires excellent rapping abilities on top. This is no easy task, and isn’t all that’s demanded from Angelica, as she also has some pretty high notes to hit in her songs. Conveying the jealousy and longing of Angelica alongside the deep love she feels for her sister is also a tricky prospect. This role requires a lot of talent for the performance to be considered satisfactory.

#19: Veronica Sawyer

“Heathers: The Musical”
This protagonist just can’t catch a break; she gets bullied, her boyfriend turns out to be a murderer, and she has the most vocally challenging role in the show! While Heather Chandler has some difficult notes and riffs to hit in her songs, Veronica has to do it on a much higher scale, with a large number of pop rock songs, hard riffs and impossible belts. Portraying the inner struggles of a high school girl who has to deal with accidentally aiding in the murder of her peers makes this role difficult to act as well, but if done well it really is something beautiful.

#18: Tracy Turnblad

“Hairspray”
You can’t stop this crazy talented chick from dancing and singing to her heart’s content, and the woman who plays her has to be ready for it. Tracy has to carry a lot of the show with her acting, singing, and dancing, so a triple threat is required. She’s on stage for the majority of the show and has to be dancing and singing with a big smile on her face for most of it. Maintaining a bubbly attitude while working hard physically and vocally is tremendously difficult, but that’s what makes Tracy so fun and rewarding.

#17: Glinda

“Wicked”
For many actresses, this role will be the toughest challenge they’ve yet to face. With some impressingly high notes to hit, and having to juggle between her head voice and her mix range, Glinda requires strong vocal ability for anyone wishing to take on the role of the Good Witch of the South. The actress also needs to balance the character’s “dumb blonde”, popular-girl personality with the surprising depth of Glinda that the audience is gradually introduced to. In addition, the chemistry between Glinda and the other lead, Elphaba, is what the whole show centres around, and thus needs to be strong. Speaking of, we may see more of our green friend in a little bit...

#16: Mrs. Lovett

“Sweeney Todd: The Demon Barber of Fleet Street”
She may have the worst pies in London, but she’s also got some of the trickiest songs! As in many shows written by Stephen Sondheim, the songs for Mrs. Lovett are tough in large part due to the fast and constantly changing tempos. The actress who takes on the role has to be a master of controlling her breath to be able to sing these songs as they’re meant to be sung. What makes the role even more challenging is that Mrs. Lovett as a character is a demon to figure out. She needs to be seen as caring, in love, and murderous. Not exactly a walk in the park.

#15: Velma Kelly

“Chicago”
This is a really killer role. Being able to do this kind of intense jazz dancing throughout the show requires real talent, and to do it while singing at the same time? Unfortunately, Velma has to do it alone. This femme fatale also has to make an audience love her, despite the fact that she’s, well, you know, a murderer. This triple threat performer may not be the star like Roxie, but she’s got a lot of work to do. When done well, this role is a real showstopper, as numbers like “Cell Block Tango” can attest to.

#14: Norma Desmond

“Sunset Boulevard”
Not only does Norma Desmond have to perform some of Andrew Lloyd Webber’s greatest songs, the actress has her work cut out for her in trying to portray a delusional former starlet. The character is stuck in a fantasy, reliving her glory days in some heartfelt songs, both conveying a sense of greatness and madness to the audience. Norma needs a magnetic stage presence that’s incredibly compelling and also slightly frightening, and did we mention the songs? The range required for these is typical of Webber’s work, but just because it’s expected doesn’t mean it’s easy.

#13: Kim

“Miss Saigon”
This role is an absolute beast. It demands a lot of emotion, power, and presence from a relatively young actress. Moreover, Kim sings pretty much every other song, and these songs are tough to boot. This dynamic performance would be hard for anyone, but forcing a young actress to tackle the themes of love, abandonment, heartbreak, and sacrifice in a very real way is a challenge. Kim may be fictional, but her experience was very real for many in Vietnam, and capturing those intense emotions and turning it into a performance is very difficult.

#12: Grizabella the Glamour Cat

“Cats”
The roles on this list are all difficult in their own, unique ways, but for the vast majority of them, the actresses at least get to play humans. Imagine having to sing some powerful Andrew Lloyd Webber songs, portray a deep nostalgia and longing for acceptance, while also...playing a cat. Grizabella’s song “Memory” is phenomenal and one of the most mainstream musical theatre songs of all time, and so taking on the role has the added pressure of handling this famous and heartfelt ballad.

#11: Christine Daaé

“The Phantom of the Opera”
It should be no surprise to see another Andrew Lloyd Webber role is on this list. Musically, this is one of the most challenging roles out there. Christine requires a high soprano singer who has at least studied classically and knows opera techniques. Moreover, Christine is on stage for most of the show and is constantly singing, meaning she has very few breaks. Christine’s high note at the end of the titular song is so hard to hit, in fact, that the actresses are said to pre-record the note in case they feel that they cannot hit it during a show, lip-syncing instead. That’s completely understandable; having to hit that even a few times a week could really destroy your voice.

#10: Caroline Thibodeaux

“Caroline, or Change”
Though the mood of this musical is low nearly throughout - following the story of an African American maid to a Jewish family in the 1960s - it never stops singing. And for the actress playing the titular role, that means much of the singing is hers, be it in solo or group numbers. Telling a beautifully honest tale about the working poor through blues, spirituals, and folk music, this actress must keep the audience engaged while keeping the character true to her bent but not broken nature. It is tough, but dang, is it worth it to tell this heartrending story.

#9: Effie White

“Dreamgirls”
This decade-spanning story about love and betrayal in the music industry is certainly going down in history as one of the greats. And with a gorgeous amount of confidence in her dream and in herself, the emotional role of Effie White is one for the ages, but not at all for the faint of voice. With a beautiful mezzo-soprano and insane belting, this role is only for the brave. Especially, as we all know, with the crazy “And I Am Telling You I’m Not Going.”

#8: Elle Woods

“Legally Blonde”
Though you need a killer soprano voice to bring down the house as Vivienne Kensington, it is the lead of this musical romantic comedy that takes this spot. With dancing skills to pay those Harvard bills and crazy vocal abilities, the part of Elle Woods demands a lot of its actress. Plus, with the movie franchise, any pink-clad daughter of Delta Nu has a lot to live up to. But you can also learn a lot from Elle Woods, like how to win a court case with hair care knowledge and of course, how to bend and snap.

#7: Fanny Brice

“Funny Girl”
From Follies girl to vaudevillian star, that is the life of Fanny Brice that this Broadway classic follows. But while Fanny is fun and - obviously - funny, her role is also incredibly taxing. With costume changes galore and a need to almost constantly be on stage, this part could easily wear out a less experienced actress. This, plus the vocal demands are crazy as hell. So, we don’t mean to rain on your parade; just prepare for some intensity when taking on this role, but always have fun.

#6: Reno Sweeney

“Anything Goes”
Tie on your dance shoes tight for this one, ladies. Reno Sweeney will keep your feet flying throughout this stamina-breaking musical. Not only that, but you have to keep on singing too? Yes, there is a lot of energy required to play this outspoken gal. And with such intense demands of the actress, you either have to give it your all or give nothing at all. So, if you’ve got the itch and the talent to play a funny, confident, and sassy nightclub singer, we propose anything goes.

#5: Elphaba

“Wicked”
From her days as belt-crazy role of Maureen Johnson in “Rent,” we all know Idina Menzel has left behind some tough but highly coveted shoes to fill on The Great White Way - and “Wicked”’s Elphaba is certainly no exception. With the ability to make the audience love her while knowing she’ll ultimately become the wickedest villain in Oz, it takes a special type of woman to take on this role. Mix that with some of the most powerful numbers on modern Broadway - both solo and duet - and you’ve got yourself one green-skinned powerhouse of a part.

#4: Diana Goodman

“Next to Normal”
As the plot of this musical unravels, it reveals that, like every family, there is more going on behind closed doors and the unsteady center of this story, Diana Goodman, has it the hardest. Playing a suburban mother who suffers from bipolar disorder, as well as delusions of her dead son, is quite the difficult role. This modern musical touches on subjects that hit close to home for some and make issues of mental illness more accessible to those who have not always understood them. As such, this heavy matriarch role is one that must be played with an understanding hand but emotionally raw voice.

#3: Celie

“The Color Purple”
This powerful musical adaptation of Alice Walker’s novel might have only had a few years on The Great White Way, but that has not stopped it from having international success. And over the course of this melancholy story, Celie grows and changes right before the audience’s eyes. And much of the drama of this musical rests squarely on her shoulders as she loves and learns the ways of the world she lives in. And with jazz, the blues, and other folk and soul sounds riddled throughout this classic tale, it takes a strong woman to carry that weight.

#2: Eva Peron

“Evita”
This Broadway classic follows the true rags to riches story of Eva Peron as she steps into the limelight of 1940s Argentina. And the moment she takes the stage, it’s clear she’s a presence to be reckoned with. Much like Celie, the audience watches this incredible character grow from a young girl into a powerful first lady of her home country. With each song being a monologue, turning the page on a new chapter of this amazing woman’s life, an actress must handle this role with a strong voice and acting range. But if you wish to join the ranks of Patti LuPone and Madonna, Argentina just may be crying for you.

#1: Mama Rose

“Gypsy”
Long before the days of Honey Boo Boo and Mama June, there was Mama Rose, pushing her daughters into the limelight, in order to live vicariously through them. And “Gypsy” puts this quintessential stage mom’s descent into madness on full display. Carrying most of the weight of this musical right up until the final killer number, this hellish tour de force takes a lot out of an actress with raw passion and wild emotions. The energy level required of this role could drain even the best of actresses. And you best make Mama proud.

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