12 of the Best Pairs of Musicals to Watch Back to Back

Wine and cheese, peanut butter and jelly, tequila and bad decisions, vast…tracts of land – it's just a fact that things are better in pairs, and musicals are no exception. Now, I'm not saying these musicals are precisely alike, but they do strike a similar tone – like Netflix "if you enjoy this, you may want to check out this as well." The musicals I have expertly paired together evoke a lot of the same feelings and compliment each other, making for a great double feature.

The qualifications for making my list (in honor of Hamilton releasing on Disney+), is that each musical has to have been staged (typically on Broadway or West End) before being adapted for film. And that's about all of my qualifications. Without further ado, please silence your cell phones and refrain from flash photography during the performance. Thank you, and enjoy the show.

  • The Sound of Music (1965) / Evita (1996)Weekend Evergreen - Best Movie Musical Pairings

Of course, we start the list strong with the epitome of musical adaptations, The Sound of Music. I mean, Julie Andrews and Christopher Plummer? You had me at Julie Andrews. But then again, Madonna stars in the latter, and it is solamente perfecto. I mean, history, musical icons, and songs everybody knows? Yes, please.

  • Hello Dolly (1969) / My Fair Lady (1964)Weekend Evergreen - Best Movie Musical Pairings

Not quite as iconic as the first pair, but this continues on with the legendary women stars. The stories are cute, there's romance and big feathered hats and gorgeous dresses and production numbers. Besides, this pair has Barbra Streisand and Audrey Hepburn – do you really need more reasons?

  • Guys and Dolls (1955) / Little Shop of Horrors (1986)Weekend Evergreen - Best Movie Musical Pairings

These two are both cheeky, have some stellar performances by musical legends, and have each cemented their legacy in pop culture beyond just Broadway. They're a little quirky and full of characters and wacky situations, with a 50s flair. Yes, I'm bending the rules a bit as Little Shop was

  • West Side Story (1961) / Grease (1978)Weekend Evergreen - Best Movie Musical Pairings

These go together in that "love story with a twist" kind of way, with a splash of coming of age / rebellious teenagers. Just watch out for those sharks – I hear they've gotten into some greased lightning.

  • Jesus Christ Superstar (2000) / Joseph and the Amazing Technicolor Dreamcoat (1999)Weekend Evergreen - Best Movie Musical Pairings

Bible musicals? Why, yes, we have two. Both of these Andrew Lloyd Webber shows use the good book as a basis, with the first being a little edgy for the more conservative crowd but incredibly good. Personally, I prefer my Jesus Christ Superstar in the form of 2018's television concert with John Legend and Alice Cooper, though there's really not a bad version.

  • Cinderella (1997) / Into the Woods (2014)Weekend Evergreen - Best Movie Musical Pairings

Okay, so I have to admit I'm not a big fan of Into the Woods despite doing the musical in college, and it is wildly popular, but for me, Cinderella more than makes up for my feelings about Into the Woods. I mean, Brandi as Cinderella? Sign me up! Both are fairy tales with an edge, and they're great. Though I suppose you could watch the 1950s Cinderella movie version, but come on – that doesn't have Whoppi Goldberg.

  • Hairspray (2007) / Bye Bye Birdie (1963)Weekend Evergreen - Best Movie Musical Pairings

Welcome to the swingin' American Bandstand inspired mid-century movie musical section! They both paint a very vivid picture of the 1950/60s, and I am living for it. I mean, the hair and fashion aside, the stories are cute and comfortable, and the music is nostalgic while never getting stale. Okay, so I know that Hairspray was originally written as a film, but then it was adapted into a Broadway show, and the 2007 movie was adapted from that production, so I'm counting it. Besides, Baltimore and Conrad Birdie are a match made in heaven!

  • Cabaret (1972) / Chicago (2002)Weekend Evergreen - Best Movie Musical Pairings

Yes, I'm grouping both Fosse musicals together, not only because they feel similar, but because they both bring something similar to the screen. No, that something isn't Liza Minelli vibes, though she is amazing and did win an Oscar for Cabaret. These similarly staged musicals both detract from large set pieces and focus on the stripped-down dance, with basic but chic costumes that highlight the out-of-this-world vocals and precise dance numbers. 10 out of 10 jazz hands across the board for this double Fosse feature.

  • Hedwig and the Angry Inch (2001) / Dreamgirls (2006)Weekend Evergreen - Best Movie Musical Pairings

Both are a little grittier in story, but they have heart and soul coming out of everywhere possible. Both of these shows are bursting with heartbreak and power ballad anthems, but not in an overly depressing way. Bring me all the lady rockstars who are fabulous from the tops of their wigs to the tips of their heels, please.

  • Oklahoma (1999)/ South Pacific (1958)Weekend Evergreen - Best Movie Musical Pairings

One has singing country-western Wolverine, and the other has…happy talk? This may be a little bit of an odd pairing, but I've always put the two together in my mind. Both of these are staples of the musical theater world, and have multiple movie adaptations, though I'm personally a fan of the 1958 movie of South Pacific and for Oklahoma, you know the only one that has singing Hugh Jackman in it is the 1999 film.

  • Annie (1982) / Oliver (1968)Weekend Evergreen - Best Movie Musical Pairings

Okay, I'll be real – I really wanted to pair Annie with Billy Elliot, but the latter was written as a film then adapted for the stage. However, that said, Oliver is a perfect pair for Annie. I mean, they're both scrappy orphans fighting to change their stars and adjust to their new lives. Plus, the characters are iconic and the songs catchy, and isn't that what musicals are all about?

  • Les Miserables (2012) / Sweeney Todd (2007)Weekend Evergreen - Best Movie Musical Pairings

I have to admit; I can't make it all the way through Les Mis without falling asleep. I've tried – in the theater, in community theater, in the cinema, at home on my couch…I just can't seem to make it through the whole thing in one go. However, if you can and still have an appetite for another musical, I highly suggest pairing this French number with this lovely Sondheim. If not, Sweeney Todd pairs nicely with Little Shop of Horrors as well for a spooky theme.

And as an extra bonus for all the readers over a "certain age" (shout out to my parents), I have been told I have to include Camelot on this list, despite me having absolutely no idea what that is. So…yay Camelot? I think I'm going to leave this one un-paired because those who watch this are likely to fall asleep ten seconds into a second movie. Enjoy your knights and round tables, and don't forget to wear a mask and take extra fiber.

No matter how you watch your movie musicals, be sure to enjoy a little bit of magic this summer as we appreciate theater and the arts more than ever while theaters are still shuttered, and thousands of performers are out of work.

About Eden Arnold

With over a decade of writing experience and by-lines in print, books, and online in addition to a lifetime of television watching experience, Eden is passionate about combining the two. Obsessed with all things TV, she is thrilled to bring all of her many television opinions to the masses.

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