Greatest Classic Movie Musicals

Ever since people first put sound in movies, the classic genre of the musical has thrived. It makes sense, of course. Song has always been involved in visual story telling. The Greek Chorus would sing prayers during stage productions. Opera adapted the works of Shakespeare.

But there is something charming about the classic movie musicals. Whereas modern musicals try to subvert and alter the genre, the classic musical exists in a pure universe. Few films have managed to successfully blend song and sight, but these few classic movie musicals have endured the test of time to leave a mark on the history of time.

The American Film Institute regards this film as the greatest musical of all time. Oddly enough, other entries on this list seem to have remained more popular with audiences over the years. While Singin' in the Rain is undeniably an iconic classic, it is not discussed as often among audiences the same way that some of the later films still are.

Regardless, Singin' in the Rain is a masterpiece. Perhaps one of the reasons why film critics love this one is that the film itself is about the story telling process. Gene Kelly plays a silent film star who is forced to work with a pompous stage actor played by Debbie Reynolds on a new film... but when talkies start gaining popularity, the silent film becomes a talkie. Hilarity ensues.

The story alone is compelling—romance, history, meta-filmmaking—but what makes this film a classic is its dance choreography and songs. It's a shame that, after watching A Clockwork Orange, the titular song will trigger nightmarish visuals.

On a personal note, watch A Clockwork Orange. It's one of my favorite films ever.

Ranked second in AFI's Top Musicals (I swear I'm not just going to regurgitate AFI's list, as I disagree with much of it), West Side Story is arguably Robert Wise's most critically acclaimed, masterful films.

But it's more than just a great musical. It's also a masterful adaptation of Shakespeare's Romeo and Juliet. Only two filmmakers have really managed to take the plot of Shakespeare's plays, and remove all the dialogue, settings, etc, yet retain the greatness of the play. One is Akira Kurosawa, who did it multiple times (Thrones of Blood and Ran are Macbeth and King Lear, respectfully), and Robert Wise.

Wise takes the plot of the original play—a play that only makes sense if you understand the feudal political system of houses and the like—and translates it to modern day without losing any sense of credibility. If anything, West Side Story is better than the original play, or, at the very least, more realistic.

Yes. The play where a bunch of fully-grown men start spinning, dancing, and singing is more realistic than Shakespeare's most popular tragedy.

Oh, and the songs! The songs are breath taking. Every song is charged with emotion, passion, and pushes the plot forward in an epic manner. It's awesome.

The Sound of Music is a beloved classic. By no stretch of the imagination is there any doubt of this. It's earned all sorts of accolades. AFI ranked it among the top musicals ever made. It won five Academy Awards. Its live performance on television started a trend of awkward live musicals from then on. And Vin Diesel referenced it in his classic film The Pacifier. When disposable entertainment starts referencing your film, you know you've hit it big.

And yes, I know Robert Wise directed this film, too. The 60s were a good time to be Mr. Wise. Between this, West Side Story, and The Haunting, he made a few certified masterpieces.

The film features a nun played by the lovely Julie Andrews who is sent to watch over a rich captain's children. The captain, played by Christopher Plummer, is a cold, orderly man whose heart is warmed by the precious Julie Andrews and her singing voice... but then war breaks out, and this scenic film is disrupted by Nazis! Just more proof that Nazis ruin everything... but make films better.

The music in this movie is top notch. Few films have ever managed to capture the grandness of life and adventure as these. The songs bounce from epic to sweet and endearing to—well, the whole gamut of human experience.

While the two halves of the film may feel a little contradictory, seeing as how it goes from a casual romantic story to a war escape film halfway through, it is undeniable that this is one of the grandest, most incredible movies ever made.

Okay, so these four films are literally the top four films the American Film Institute ranked as the four best musicals ever made, but these movies are all so perfect that, yes, they deserve to be here. The Wizard of Oz is arguably one of the greatest films ever made.

The songs in this film have become iconic in their own right. I dare you to listen to "Somewhere Over the Rainbow" and not be completely consumed by wistful dreams of paradise. I dare you. Or sweet dreams of some kind.

But more than just the songs, the production value for this film is incredible. Consider that this film is perhaps the oldest movie on this list, yet remains breathtaking and beautiful to look at. This was one of the first color films ever. And look at it! It's beautiful!

And think of all the other musicals and movies this masterpiece spawned! The Wiz. Wicked. And Return to Oz. You remember Return to Oz, right? The movie where Dorothy gets electroshock therapy and a woman casually decapitates herself? It's a family picture.

Based on the already popular stage play, this classic Audrey Hepburn film is, in many respects, another musical influenced by Shakespeare, specifically his early work The Taming of the Shrew. But while that play has aged horribly due to its suggestion that women should be trained by starvation and beating, My Fair Lady presents a classless lady being made... classy.

It is a classic romantic story full of sass and wit, but what elevates this above the usual romantic affairs is the music. It is at once funny and adorable, all at the same time. (A personal favorite of mine for whatever reason is "Get Me to the Church On Time," which for the life of me always gets stuck in my head).

But that said, this musical can be a bit problematic. It can be hard for some people to stomach a woman being forced to be "acceptable" by society's standards, and that's a totally fair critique. If that idea bothers you, don't watch this film. But you will be missing out on a sweet romantic story that is, admittedly, showing its age in the 21st century.

This classic story is an adaptation that the original author, until her dying day, utterly loathed, thanks in part to Walt Disney prying the film rights from her cold, proper fingers. Thankfully, the rest of the world does not share the original author's opinion. Mary Poppins is a masterpiece.

This film, much like The Wizard of Oz, embodies this quality of childlike innocence and purity that makes it sweet dreams fuel throughout. This is perhaps the Sherman Bros' best soundtrack, since each song is immediately unforgettable and iconic. In many ways, I feel that the songs overshadow the plot itself.

Though the plot is very good (and has a lot of subtle scenes that are surprisingly moving and effective), it is impossible not to draw comparisons between Mary Poppins and The Sound of Music, as each deal with Julie Andrews coming to watch the children of a rich, emotionally distant father. Sure, one has animated characters and Dick van Dyke, but the other has Nazis.

In the end, I would wager that The Sound of Movie is a better film from a purely objective film, but Mary Poppins might be more enjoyable. In part because it's shorter. Robert Wise's masterpiece is three hours long, as opposed to Disney's two-hour and twenty minute film. But while The Sound of Music feels even longer than three hours, Mary Poppins feels like a breeze with its frenetic energy.

I also recommend watching Saving Mr Banks, which tells the story about the making of the film... even though they change the ending. If it was real to life, it would have ended with Emma Thompson's character loathing Walt Disney until her dying day, and being happy when Disney died a few years later from lung cancer.

The last film Walt Disney made before his death, The Jungle Book is arguably not his best film. Classic Disney can be a list in and of itself on this site, but while this adaptation of Rudyard Kippling's story may not be Disney's magnum opus, it certainly has an excellent sound track.

This jazzy film tells the story of Mowgli, a little boy raised by wolves, being taken to the human world after years of living like a wild animal. Along the way, hijinks ensue.

The songs in this film are immediately memorable, and all of them leave you wanting to dance along. The film, though, loses a few points for a glaring misstep Disney took. Why do you have vultures designed after the Beetles, and then NOT give them a Beetles-like song to sing? Does anyone else see the glaring misstep there?

The songs in this film are so good they even used them in the live-action film, which, might I add, is not a musical.

With the recent passing of Gene Wilder, it has become only more clear that this film is a timeless classic. Multiple generations remember this masterpiece and love it, and no creepy Michael Jackson-esque Johnny Depp remake can eclipse the original's grandeur.

But people forget it's also a really good musical, too.

Sure, not all of the songs work as well, but "Pure Imagination" has become pure sweet dream fuel for a generation of children. It's almost enough to overshadow the fact that the film is full of child torture and bodily mutilation. And who hasn't thought about singing "I've Got a Golden Ticket" when you're opening up a chocolate bar?

But, of course, Gene Wilder is the real star of this movie. He's what happens if Mary Poppins and Lex Luther had a child. Part mischievous mentor, and part evil billionaire who delights in the torture of others. Childhood classic.

Nothing is more romantic than a film about a con artist who gets away with everything in the end.

The Music Man is a perplexing story of financial fraud and romance that somehow has become a family classic. It teaches the lesson to families that lying is totally okay if, somehow, you pull something out of your ass at the last second to make everything alright.

And, not just that, but you can make people who don't trust you like you just by singing songs about librarians to them.

While there was a remake with Matthew Broderick a few years back, the original is by far the best.

It's not uncommon for a song in a musical to end up being iconic in its own right. It's quite another thing for that song to become one of the most played songs in the history of the world, but hey, the holidays.

I admit that part of the reason I am including this on the list is because of the film's legacy. While the film is still a very good movie, it is a little stagy and stiff at times. You can tell that the elaborate sets are just that: sets.

But there's something so magical about this film that you can't forget it. It possesses a charm that puts you in the holiday spirit. And the end song is simple. Little choreography, little elaborate stuff... but it's just so magical that you just love it all the same.

The classic musical about sailors on shore. It may be a little cheesy by today's standards (but if you're this far down a list of movie musicals, you probably are okay with a little cheese), but it has this endearing, innocent charm.

It's one of the few films to pull off male machismo in a way that completely subverts machismo. I mean, yes, these guys are all sailors, and one of them only wants the girl, but look at those outfits! They look like they just walked out of a Village People music video.

I kid, of course. The fact that this film is so memorable that you can make fun of it like that proves it is doing something right. And the opening number, "New York, New York" establishes the tone and plot of the film in a compact, exciting, and memorable package. It is in so many ways the perfect musical opening.

Though it is also insanely cheesy.

Yul Brynner's iconic performance, this film may not have aged all too well. Modern audiences may find certain elements of the plot a wee-bit racist. Okay, actually very racist. Yul Brynner is not Asian. None of the Asian characters are played by Asian actors, which can be highly problematic to a modern audience.

But if you are willing to ignore that (or able), you have a classic, beautiful movie about a school teacher hired to teach the King of Siam's children. The movie is a sweeping epic with beautiful sets and scenery, but, on top of all that, it's also a compelling romance for families to enjoy. It has an innocent naivety to it. Like a lot of great musicals, it feels like a fairy tale.

The film is an adaptation of one of the most successful stage plays of the 50s, and has, naturally, been adapted and readapted multiple times. But his is by far the definitive version. Of course, there's also a 90s animated adaptation that adds dragons. I believe some of the people involved refer to it as the "biggest mistake of their career" to make the film.

I admit that I'm surprised more people don't rank this film up higher when talking about classic movie musicals. While this film may not be a great "film" in the sense of narrative and the like, it has become something of a classic for a whole generation of kids growing up in the 80s and 90s.

In many respects, it is a typical story. Special orphan kid meets rich adult who adopts them. It is the same Cinderella Story we've seen a million times before. But what makes Annie special is the music. While not all the songs are instant hits, enough are masterful enough to become iconic classics.

A film becomes a classic when other films can use imagery from the film as visual shorthand. Just the image of a red haired orphan kid with freckles is enough to trigger recognition in any casual audience member.

Also, Tim Curry is in it. That's enough to make it good. Speaking of him...

Yes. This film is a classic. Fight me.

How many other films have been in theaters for as long as Rocky Horror? This film revolutionized the film industry by almost single-handedly creating the genre of the Midnight Movie. It changed the musical forever after its release.

Oh, and it's also really, really good.

It deals with some really complex deep themes such as sexual identity, individuality, and the nature of evil, all while being a seemingly chaotic mess of a film. But, by being a mess, it manages to successfully relay an idea that takes a few viewings to really appreciate.

And not just that, but it's also a nostalgic look back at the classic sci-fi/horror films of the 30s, 40s, and 50s, referencing and drawing from them to craft a then-modern—hell, still modern—fable.

I understand this selection is controversial. Most people would probably put Grease here instead, as, like Rocky Horror, it is a nostalgic piece responding to the 50s, but I think that Grease is actually kind of awful. Sure, the music is nice, but what's the moral of the film? Change everything about yourself for a man? (Don't tell me that John Travolta changes first. He doesn't do anything for Sandy, yet she has to change everything for that putz? Forget it.) Whereas Rocky Horror has better music, better characters, and ends with the moral to be yourself, regardless of how crazy and ridiculous that self is. I would argue that Rocky Horror's perverted message is far better than Grease's sexist one.

Fight me.

I understand that this is the newest entry on this list. But the movie is more than twenty-five years old. I think it qualifies as a classic by this point. Look, I had to debate not putting Dancer in the Dark on this list, but I figure that belongs on a contemporary musical list. Also, it's dark, horrible, and depressing.

During the 90s, Disney Animation hit it big with a lot of hits. Aladdin, Mulan, The Lion King... some of the best family films ever made. And a lot of their animated films also had amazing songs. Some dealt with being an awesome thief. Others dealt with being kings. And some dealt with creepy old men lusting over women a fifth their age while also fantasizing about murdering them. Yeah. Family films.

But only one of them got a Best Picture nomination.

This... full disclosure, of all the films on this list, this one is my favorite. I adore everything about this film. The characters. The songs. The imagery. The animation. Everything about it is just perfect. It is perfectly paced, perfectly written, everything.

And the songs are beautiful! Every single one of them is memorable and majestic. And, unlike a lot of epic musicals, it doesn't take three hours to finish. It's a reasonable watch that isn't obnoxiously long.

This movie is perfect.