40. “Gypsy”
Mama Rose is arguably the single most iconic and coveted female role in musical theater, period. Despite the fact that the show is based on the life of burlesque superstar Gypsy Rose Lee, the show focuses on her mother, Rose, and when I say everyone who’s anyone has played her, I mean it: Ethel Merman, Elaine Strich, Angela Lansbury, Tyne Daly, Bernadette Peters, Bette Midler, and, most recently, Patti Lupone. Barbra Streisand is still trying to get a movie version off the ground, starring as Rose herself. I’d die if this happened. Die.
39. “Fiddler On The Roof”
A fiddler on the roof sounds crazy, no? But a musical about a community of oppressed, poor, Jewish people in Imperial Russia managed to steal the hearts of fans all over the world. I guess, like me, they were just suckers for Zero Mostel’s semitic good looks.
38. “Sweet Charity”
Christina Applegate as Charity is still, to this day, one of the best casting choices for a musical, and it was the beginning AND end of her stage career. She broke her foot in previews for the show and instead of closing the show, she convinced producers to keep it going, dancing on it despite her foot being broken, and, as such, did a ton of additional damage to her foot. Fun fact: did you know when Applegate’s contract ended, they offered Britney Spears the role, but she turned it down? True story. Probably would’ve been a good move for Brit-Brit, considering this was in 2006.
37. “Company”
Another musical made better by the appearance of Neil Patrick Harris, only this time, he brought someone equally charismatic and amazing with him: Stephen Colbert. That’s right, “Company” is a Sondheim musical written in the ’70s that never really got a ton of credit for being a very progressive show about relationships and other adult themes until a star-studded concert version hit Lincoln Center in 2011, starring NPH and Colbert, as well as Anika Noni Rose, Jon Cryer, Christina Hendricks, and Patti Lupone.
36. “Pippin”
Make no mistake, “Pippin” is one weird show. It’s a show based on the real life characters of Charlemagne and his son Pippin, but it has little to no historical accuracy. It turns out to be a show within a show that regularly breaks the fourth wall, and at times it’s hard to tell if what’s going on on-stage applies to the show or the show within the show. It’s hella confusing, but still amazing.
35. “Mamma Mia!”
While not the first jukebox musical by any stretch of the imagination, “Mamma Mia!” is certainly the most iconic musical based on an assortment of songs by one artist, in this case, ABBA. “Mamma Mia!” has been on Broadway for what seems like forever, and it is an unstoppable moneymaker. It even inspired a movie, which taught us that even a terrible idea featuring actors who can’t sing (cough, Pierce Brosnan) can still make $600 million. It’s been keeping audiences dancing in the aisles for more than a decade, so those terrible commercials tell us.
34. “The Little Mermaid”
As a disclaimer, I am unabashedly using the fact that “The Little Mermaid” was turned into a musical just so I can talk about how much I love “The Little Mermaid.” Only Disney could turn a horrifying Hans Christian Andersen fairytale into a universally beloved icon. “The Little Mermaid” was considered by many to be “the movie that brought Broadway into cartoons,” thanks to the legendary musical duo of Alan Menken and the late, great Howard Ashman, who “gave a mermaid her voice” and breathed life into, for my money, the greatest Disney song ever: “Part of Your World.”
33. “Hairspray”
Come on. You know you want to start singing “Good Morning Baltimore” every time you wake up, regardless of where you live. It’s just such an infectious melody. That’s the timeless appeal of “Hairspray,” despite the fact that it came from a creepy John Waters movie.
32. “Godspell”
Never were religion and musical theater better combined than in Stephen Schwartz’s insta-classic “Gospell,” which definitely shared a few ideas with “Jesus Christ Superstar,” both of which came out around the same time. Godspell was a lot more subversive and experimental than “Jesus Christ Superstar,” but, well, any time you can go out for an audition for the part of Jesus, that’s a pretty cool part to have, no?
31. “The Wiz”
This one is definitely on here for the movie version, not the Broadway version, but considering the film starred Diana Ross as Dorothy, Richard Pryor as The Wiz himself, and the one and only Michael Jackson as the Scarecrow, and not to mention the music and lyrics by Luther Vandross and Sidney Lumet, Joel Schumacher, and Quincy Jones at the helm, how could you leave this off? Nobody beats “The Wiz.”