Toughest roles to sing

The Phantom is a pretty vocally demanding role.

Elphaba requires a lot of vocal energy.

Evita is one of the most vocally demanding roles

Drew in Rock Of Ages

If Mimi, Maureen and Collins go balls to the wall, those are pretty vocally demanding

As far as I know, the rock opera "The Fork" by Andy Simpson was written, but never staged, due in part to the role of Adolf Hitler (appearing in one scene, one song only) being not just vocally demanding, but physically vocally devastating. Singing somewhere between very high rock tenor and castrati, the part is written to fall NOWHERE in falsetto and simply be howled and screamed out.

Elle Woods sings about 80% of the show. Maybe more.

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I agree that although they may not be as difficult as Eva in EVITA, roles like Roger and Elphaba can be very difficult if not done correctly.

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sweeney, sweeney, sweeney, SWEEEEEEEENEY! (and pirelli even though he has very little stage time)

and Brooklyn.

What about all the traveling salesmen in The Music Man's opening number? And for that matter Harold Hill? I mean, "Ya Got Trouble" can be very frustrating to get just right.

I would agree with Victor and Adrian in Smokey Joe's Cafe- for Victor, I Who Have Nothing alone is a struggle to sing.

I would add Rose in Gypsy. That is one tough score.

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If you actually go by the score, not how it was altered for the Broadway cast, Mayor Matilda in All Shook Up is ridiculous. She's expected to pop out High G's like Pez in a bi-polar flamenco/rockabilly comedy number. It's absurd. Thank goodness the character only has one song if that's the vision of how she should sing.

Actually, the entire vocal arrangement of that show is ridiculous. All the female characters are written for high belters (3 have to slide into High F/Gs), and the male characters are either high tenors or full on schticky voice (or both, poor Dennis). All that effort for something that, on a good day, is best described as just ok. Don't even get me started on the choral numbers; I'll have nightmares again.

Edgar/Bat Boy in Bat Boy is very vocally demanding. Wide vocal and style range, plus all the primal screaming at the beginning and rock screaming at the end.

It's been years since I've looked at the show, but I seem to recall The Wind in the Willows having some hard vocal parts (Mole, maybe? Very wandering wide-rang melodies. Evil Weasel has a shrieking high tenor number in Act I). Then again, who even knows that McGough/Perry show, anyway?