Best Musical Winners I’ve Seen, Ranked

The majority of my favorite musicals haven’t won the coveted Tony Award for Best Musical. In fact, few of them have. However, I’ve seen nearly 20 shows that did win this accolade, and I thought I would rank them purely based on my enjoyment of the show. Please note that I’m not ranking the following musicals based on how good they are, simply based on how much I personally like them.

Additional note: I’ve also seen Billy Elliot, Hairspray, and The Lion King, but I was too young when I saw them to rank them on this list.

16. A Little Night Music (1973)

I saw this musical at Stratford, and while the actors were undoubtedly talented, I did not enjoy the musical at all. The plot was annoying and while the music was gorgeous, I was too anxious about the plot to enjoy the songs at all.

Catherine Zeta-Jones as and Alexander Hason in A Little Night Music. Photo courtesy of Joan Marcus.
Catherine Zeta-Jones as Desiree and Alexander Hason as Frederik in A Little Night Music.
Photograph courtesy of Joan Marcus.

15. Jersey Boys (2006)

I don’t remember this one too well, but I remember it well enough to rank it. Like many others on this list, it’s clear that Jersey Boys has great music, but the show itself wasn’t memorable enough for me. It’s another biographical jukebox musical in an age full of them, though it really was the catalyst that sparked this recent trend.

The cast of Jersey Boys. Photograph courtesy of Joan Marcus
The cast of Jersey Boys.
Photograph courtesy of Joan Marcus

14. The Phantom of the Opera (1988)

I really don’t hate this one at all. In fact, it has one of my favorite sequences in all of musical theatre (specifically, “Angel of Music” all the way through “Music of the Night”). However, the show can get kind of dull at times, which is why I have it ranked here. It doesn’t help that people romanticize the Phantom, who is, in fact, a creepy stalker.

Ben Crawford and Ali Ewoldt in The Phantom of the Opera. Photograph courtesy of Murphy
Ben Crawford as The Phantom and Ali Ewoldt as Christine in The Phantom of the Opera.
Photograph courtesy of Matthew Murphy

13. Fiddler on the Roof (1965)

Yes, I’m Jewish. Yes, I’m putting Fiddler on the Roof third to least favorite. The music is a delight and the dancing is obviously a spectacle, but the plot of this show is simply not interesting enough to me to sustain a three-hour musical.

The cast of the off-Broadway production of Fiddler on the Roof doing the Bottle Dance. Photo courtesy of Matthew Murphy
The cast of Fiddler on the Roof doing the Bottle Dance.
Photograph courtesy of Matthew Murphy

12. Once (2012)

I hope I’m not beating a dead horse, but once (pun unintended) again, here’s another show with gorgeous songs and a dull plot. I enjoyed my overall experience seeing the show, and I would definitely see it again. However, like Fiddler, I don’t think this show has an riveting enough plot to be a two-act musical.

Paul Alexander Nolan as Guy and Joanna Christie as Girl in Once. Photograph courtesy of Joan Marcus
Paul Alexander Nolan as Guy and Joanna Christie as Girl in Once.
Photograph courtesy of Joan Marcus

11. Fun Home (2015)

I wish I could see this one again because it’s getting a lower ranking than it deserves. There are some standout songs in this show for sure (most especially “Ring of Keys”), and the show is one of the most significant musicals of this decade, but I found myself zoning out throughout. Put simply, I wasn’t as invested in the plot as I should have been.

Sydney Lucas as Small Alison & Beth Malone as Alison in Fun Home. Photo courtesy of Joan Marcus and Jenny Anderson
Sydney Lucas as Small Alison and Beth Malone as Alison in Fun Home. Photograph courtesy of Joan Marcus and Jenny Anderson

10. The Book of Mormon (2011)

I actually found to this show to be incredibly entertaining, but it’s too offensive to Africans, and Ugandans specifically, for me to completely overlook in this ranking.

The cast of The Book of Mormon.
Photograph courtesy of Joan Marcus

9. Cabaret (1967)

Cabaret is a musical I’ve seen twice now and I’ve thoroughly enjoyed it both times. The story is gripping, the music is absolutely inspired, and it has one of the most shocking finales (both act one and act two) in existence. That said, it has this ranking mainly because the length of each act is highly imbalanced, which makes the hour-and-a-half first act drag a bit.

Joey Grey and the original Broadway cast of Cabaret. Photographer unknown
Joey Grey and the original Broadway cast of Cabaret.
Photographer unknown

8. How To Succeed In Business Without Really Trying (1962)

I’ve only seen this musical once, but it is definitely one of the highlights of my theatre journey. Above all else, it’s such a fun show to watch because the plot is positively wild and kooky in the best way.

Charles Nelson Reilly, Claudette Sutherland, and the original Broadway cast of How to Succeed in Business Without Really Trying.
Photographer unknown

7. Les Misérables (1987)

Though it’s widely recognized for being one of the most depressing musicals ever written, Les Misérables is a work of pure artistic genius. It’s not a show I’d want to watch every day, but it’s one I thoroughly appreciate each time I see it.

Kyle Scatliffe as Enjolras & Ramin Karimloo as Jean Valjean in Les Miserables. Photography courtesy of Matthew Murphy
Kyle Scatliffe as Enjolras and Ramin Karimloo as Jean Valjean in Les Misérables. Photograph courtesy of Matthew Murphy

6. Dear Evan Hansen (2017)

The first time I heard “Waving Through A Window”, I knew that Dear Evan Hansen was going to be one of my favorite musicals. I know it’s simultaneously a beloved and a hated musical in the fandom, but I lean more towards the side that loves it. The music is exactly my style, and the plot is modern and intriguing, though its depiction of mental illness is why it’s not higher up on my list.

The original Broadway cast of Dear Evan Hansen. Photograph courtesy of Matthew Murphy
The original Broadway cast of Dear Evan Hansen.
Photograph courtesy of Matthew Murphy

5. Hamilton (2016)

This show is a work of art from beginning to end. It seamlessly transitions from song to song, and every single one is practically perfect. The only few reasons why it’s not number one is because I simply enjoy other musicals more, along with the fact that people’s sheer obsession with it is starting to bother me. Subsequently, this inadvertently draws attention away from other shows. In addition, fandom has started treating the extremely flawed founding fathers as fictional characters, which just isn’t right.

The cast of Hamilton. Photograph courtesy of Joan Marcus
The cast of Hamilton.
Photograph courtesy of Joan Marcus

4. Kinky Boots (2013)

The first time I saw this show was in 2013 with the original cast, and to this day it’s one of the most entertaining shows around. Everything works in harmony with this show, from the music, to the choreography, to the plot, to the production design. It’s really well put together, but most of all, its messages of self-love and acceptance of others is incredibly significant in today’s hateful world.

Stark Sands, Billy Porter and the company Kinky Boots. Photography courtesy of Matthew Murphy
Stark Sands, Billy Porter and the company of Kinky Boots.
Photograph courtesy of Matthew Murphy

3. A Chorus Line (1976)

There’s a reason why A Chorus Line won a Pulitzer Prize. It’s an original musical with a plot that stands the test of time. While each and every song is noteworthy in their own way, the choreography is even better. Also, this show is loved dearly in my family, so I had to rank it here.

The cast of A Chorus Line. Photograph courtesy of Martha Swope
The cast of A Chorus Line.
Photograph courtesy of Martha Swope

2. In The Heights (2008)

With its relevance in modern history and top-notch songs, In The Heights is one of my all-time favorite musicals. Much like A Chorus Line and Rent, you can tell that it’s a musical about real-life people living authentic lives, which makes it all the more poignant and accessible to the everyday theatregoer.

Lin-Manuel Miranda and the original Broadway cast of In The Heights. Photography courtesy of Joan Marcus
Lin-Manuel Miranda and the original Broadway cast of In The Heights.
Photography courtesy of Joan Marcus

1. Rent (1996)

In January alone, I saw the Rent national tour as well as Rent Live. After seeing both of them, I feel absolutely confident in saying that it’s my number one favorite Tony-winning best musical. I can listen to the soundtrack on shuffle for hours on end, and each and every cast brings something new to the show. Even though it has its flaws, I simply adore it.

The original Broadway cast of Rent. Photographer unknown
The original Broadway cast of Rent.
Photographer unknown

What’s your favorite Tony-winning best musical that you’ve seen? Least favorite?

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