The Best Broadway Shows

Several years ago, I was out with some friends and their friends. We were at a bar, talking and having a good time. The discussion turned to whatever the popular TV shows or movies were at the time and I zoned out, not interested in the conversation. I don’t watch much TV and usually fall asleep during movies. If you like to recite movie or TV quotes, unless it’s from “Friends,” “Big Bang Theory” or the prior day’s Cubs’ game, I’m going to look at you like you’re crazy.

One of the friends of friends started asking me about what shows I watch and when I told her I don’t really watch TV, she told me “you have no culture.”

I remember being taken aback when she said that. What? What does that even mean? Because I don’t watch TV, I lack “culture?” Again, what? I’m pretty sure I rolled my eyes at her and said “Whatever, you don’t know me.”

Her comment crosses my mind from time to time because I look at my life and know that I am pretty well cultured. I have traveled all around the USA and to many different countries throughout the world. I have friends from all over the world as well. Visiting museums and going to concerts and sporting events are things I do often. I also love to go to live theater and I have had the opportunity to see several shows on Broadway in New York. However, most of the time, I see shows here in Chicago through Broadway in Chicago.

I would say that by now, I have seen 50 or so Broadway shows. Reading reviews before going to a show is something I try to avoid because I love to go in without preconceived notions so I can make my own opinions. Since I have been to so many shows, I thought you might be interested in knowing which are my favorites and which I thought were underwhelming. So here is my list of the best Broadway shows

Disclaimer: This list turned out to be longer than I planned but I love theater so I guess it shouldn’t surprise me.

The Best Broadway Shows


  1. Wicked – This is the story of the witches from the Wizard of Oz. I saw it at least three times when it was here in its first run in Chicago and saw it again last year when it came back. I gasped the first time I saw the surprise at the end and officially decided I loved it then. It’s my favorite of all the shows I’ve seen. I HIGHLY recommend Wicked if you have the opportunity to go see it.
  2. Hamilton – I cannot do a list of the best Broadway shows and not mention Hamilton, right? Hamilton ranks second on my favorites list. It won 11 Tony Awards. I have also seen this show multiple time. A friend and I got to see Wayne Brady playing Aaron Burr the first time I was in the room where it happened. I thought the actress who played Alexander Hamilton’s wife, Aliza, stole the show. She has an amazing voice! Fun fact: JPMorgan Chase Bank owns the pistols used in the dual fight that killed Alexander Hamilton. They are housed in one of its NY offices.

    The Best Broadway Shows
    Kelley and me before seeing Hamilton for the first time.
  3. Mama Mia – I’ve seen this one in Chicago and also on Broadway in New York. I love the music – it’s all music from the band Abba if you don’t know. The play is better than the movie, although I love the movie too.
  4. Mary Poppins –The classic movie done live. This was a show I decided to go to on a whim by myself one night and I am so glad I did. Supercalifragilisticexpialidocious is the best musical number I’ve seen. I loved loved loved it!  I wanted to get up and sing along.
  5. Jersey Boys – This play is the story of Frankie Valli and the Four Seasons. I also loved the music in this one and wanted to sing along because it included so much of the music I grew up listening to with my parents.
  6. Beauty and the Beast – This was the first show I say on Broadway in New York. It was so good – it felt like I was watching the Disney animated version.
  7. Aladdin – I saw this one in Chicago with my friend Kelley. The set and costumes were amazing! And the music was good too. The magic carpet flies – and I still wonder how they did it! I didn’t see any wires.
  8. Newsies – This is a musical based on the 1992 musical film Newsies, which in turn was inspired by the real-life Newsboys Strike of 1899 in New York City.
  9. Escape to Margaritaville – Okay, this one is definitely not for everyone. It is very cheesy. BUT, as a self declared Parrothead who has been to 15ish Jimmy Buffett concerts, I loved this one. I knew most of the music and loved singing along.
  10. Something Rotten – I also went into this one not knowing what to expect. While it wasn’t quite “The Play that Goes Wrong” funny, it was pretty close. I would recommend it. What I remember most about this show was going with a friend who was struggling through a break up. Hearing her laugh during this show was the best music to my ears.
  11. Once on this Island – A couple of friends and I decided to go to this show at the last minute and I am glad we did. The cast was entirely Black, which I loved. The costumes were great and the story was okay too.


  1. The Play that Goes Wrong – I had no idea what to expect when I went to this show and it ended up being the funniest show Broadway show I have seen. EVERYTHING goes wrong, according to plan. It was incredible! I laughed and gasped a lot in this one. I loved the lightness of this one for a change of pace.
  2. What the Constitution Means to Me – This one isn’t going to be everyone’s cup of tea but as a political junkie and strong advocate for women’s rights, I really enjoyed it. This was part of a season ticket package and is one of the reasons why I like the packages. I probably wouldn’t have gone to see this one on its own. I really recommend it if political history and women’s rights are your thing.
  3. Oslo – This is the Tony award-winning play by J. T. Rogers, recounting the true-life, previously secret, back-channel negotiations in the development of the pivotal 1990s Oslo Peace Accords between Israel and the Palestinian Liberation Organization. I remember the photos from when this happened but never knew the significance or the story behind it. This is a long play and is not a musical. But it is a good history lesson.

There are two shows that I hope to see sometime in 2021 or 2022, “Six” and “Come From Away.” My friends saw Six when it was at Navy Pier last summer and still rave about it. In “Six,” the “six wives of Henry VIII take the mic to remix five hundred years of historical heartbreak into an exuberant celebration of 21st century girl power!”

“Come Away From” was also in Chicago last year. I missed it because my schedule wasn’t cooperative. Hopefully, it comes back in 2021 or 2022. If not, I may have to go to New York to check it out.

Now it’s your turn. What are the best Broadway shows in your opinion? Did I miss any? Tell me in the comments below.

To check out more from this blog, see my favorite memories from Jimmy Buffett concerts here and a Letter to My Younger Self here.

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The Best Broadway Shows

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Meet Carmen

I’m Carmen, the founder of this blog and the Vicariously Through You community. I am so glad you’re here!

I currently live in Chicago, IL, USA with my Maltipoo pup, Stella. I am 40-something, single and do not have any children.

When I am not working on this blog and growing the Vicariously Through You community, I work as a Financial Analyst. In my free time, I travel as often as I can, often as a solo traveler. I enjoy rainy days, plain green tea, Chicago Cubs baseball and books with happy endings.

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