Shakespeare and Musicals

Updated: Nov 5, 2020

Presented by Ammmy


First, a few notes!

This is not comprehensive, and it’s not trying to be! I’m mostly focusing on the biggest/most successful musicals, plus a couple personal favorites. (I’ve also made a list of some interesting ones I’m not familiar with that I discovered while researching all this. I’ll share that at the end if people want.) I’m only including musicals written in English; there are at least a few Shakespeare musicals in French and Italian, but I don’t know enough about them to say anything useful. ALSO I’m purposely not talking about film adaptations for the most part, because this was already long and that seemed like a logical place to start. All the shows from before 2010 have film versions, though, and I can talk about them another time if people want.

ONWARD (chronologically). Here’s a Spotify playlist with highlights from each show I discuss.

The Boys from Syracuse

Year: 1938

Written by: music by Richard Rodgers; lyrics by Lorenz Hart; book by George Abbott

Shakespeare connection: Based on The Comedy of Errors

Boys from Syracuse was the first hit Broadway musical based directly on a Shakespeare play. It’s a fairly direct if quite loose adaptation of Comedy of Errors, and as such is a little bit closer to “integrated” than a lot of pre-Oklahoma! musicals were, incorporating choreography by George Balanchine. That said, the book is … not great by modern standards. Rodgers also generally wrote music first, with Hart* filling in the lyrics after. Most people now are likely more familiar with the score’s stand-alone songs “This Can’t Be Love” and “Sing for Your Supper,” both of which had a lot of popular and jazz covers from the ’30s onward. If you enjoy ’30s pop, the entire cast recording is fun, though. (Original cast recordings weren’t a matter of course back in the ’30s; the “original” I’ve included in the playlist was actually recorded in the ’50s and was an active attempt to recapture orchestrations and styling from the original show.) Note there’s mainstream attitudes toward gender roles typical of the era throughout, as with most musical comedies from the time.

* If you aren’t familiar with Lorenz Hart, his life is fascinating though also quite sad! He struggled with depression and alcoholism throughout his life. He was also closeted and notoriously unhappy with his own looks, though the extent to which any of these things affected the others is obviously something we can’t know for sure. He died at only 48 (indirectly due to his alcoholism). Hart’s business partnership with Rodgers was reportedly complicated, but yielded a portion of the “Great American Songbook,” even if the shows they’re from don’t get much attention now. He was also well-regarded artistically in his lifetime; F. Scott Fitzgerald called Hart “the poet laureate of America.”


Kiss Me, Kate

Year: 1948

Written by: music and lyrics by Cole Porter; book by Bella Spewack “and Samuel Spewack”

Shakespeare connection: Based on The Taming of the Shrew

“Kiss Me, Kate” is a show-within-a-show in which 1940s actors who are also exes find themselves in an out-of-town tryout of a musical adaptation of “The Taming of the Shrew” opposite each other as Kate and Petruchio, with Petruchio also directing. If you’re thinking wow, Ammmy, that seems like it would involve a lot of really bad gender shit then you are CORRECT. The show is somewhat infamous for a scene in which the male lead spanks the female lead on stage. Revivals have tried a variety of fixes (including cutting the onstage spanking and making the song based on Kate’s last monologue “I am ashamed that people are so simple”), but given that it’s based on Shrew, there’s some fundamental things about it that are just there.

Bella Spewack, who wrote the book, was pressured to share credit for writing the script with her estranged husband, even though she did most of the work. (He punched up a subplot about gangsters, most people agree, but she did the heavy lifting.) It seems, though, she made an attempt at a moderately more progressive take before her (male) collaborators pushed back. In an earlier version of Spewack’s book, Kate within the show-within-a-show disguises herself as the boy that suggests Petruchio try to woo Kate. Spewack apparently had an interest in more agency for Kate in the Shrew part of the musical, not only the “backstage” parts. Based on letters from Porter, it seems like the director pushed to dump these changes and stick closer to Shakespeare in the “onstage” bits.

That said!! There’s a lot of fun things in this show, even in the version we did get. While I’ve mostly focused on songs that appear in the show-within-a-show in the playlist, some of the songs characters sing as “themselves” are real classics — “Too Darn Hot,” “So In Love,” and “Always True to You in My Fashion,” to name a few. The dance in this show is also usually lots of fun. (A very young Bob Fosse is Hortentio in the film version!) And, of course, this show boasts “Brush Up Your Shakespeare,” which is a delight if you can dissociate from the 1940s-ness of its take on gender. Cole Porter, king of the “You’re the Top”-style list, just goes wild with Shakespeare rhymes.

Trivia: This show is the very first Tony winner for Best Musical.


West Side Story

Year: 1957

Written by: book by Arthur Laurents; music by Leonard Bernstein; lyrics by Stephen Sondheim

Shakespeare connection: Based on Romeo and Juliet

I could easily write an entire book about “West Side Story” — multiple people have, in fact, done that — but it’s also the entry in this list you’re most likely to be familiar with already in some form, even if you aren’t a big musical person. So to keep it under control, A FEW THINGS:

  • Much like Merchant and Othello, this is a piece that continues to inspire a lot of debate over whether it can and should be produced now. Like Othello especially, it has a nasty history of productions casting white actors in nonwhite roles; this has mostly stopped (at least in professional productions), and the 2009 revival even included sanctioned rewrites to incorporate Spanish into the Puerto Rican characters’ dialogue and lyrics. That said, there are plenty of people who argue that the play is unsalvageable. I strongly urge you to check out Carina del Valle Schorske’s NYT op-ed in the sources on this point.

  • Also like Merchant and Othello, “West Side Story” is a show that’s important to the history of the form, whether or not it should be staged now. But since I’m focusing on its Shakespeare connections here, rather than musical theatre history, I’ll leave my thoughts on that alone for a future post.

  • As you probably know, the BIGGEST change from R&J to WSS is that Maria (Juliet) lives. But it’s also worth considering two other big differences: First, everyone involved in the feud is young. Lord Capulet is either cut or conflated with Tybalt (somewhat depending on the actor/director’s choices about Bernardo and his dynamic with Maria). Anita is more of a peer, if a slightly older and wiser one, to Maria than the nurse is to Juliet. Second, the few older figures who remain aren’t neutral! Schrank, the Prince’s analogue, is overtly racist toward the Sharks, even if the Jets also see him and Krupke as antagonistic figures. Doc, the Friar Lawrence equivalent, is much more passive than Lawrence and has almost no direct relationship with Maria except through his worry for Tony. While R&J is arguably about the senselessness of the feud, wherever you come out on WSS’ politics, the text is clear that the Sharks and the Jets do not face an equal playing field.

  • On a related note, the creators made the very purposeful change that Tony (Romeo’s) death isn’t an accident. Instead of bad luck in the form of a quarantine, the news of Maria’s “death” getting to Tony is 100% a deliberate outcome of the Jets assaulting Anita on her way to reach him with a message. (Whether this change is more or less effective is personal to you, but it was a very focused and deliberate change in a show that otherwise adheres pretty close to R&J’s structure.)

  • Side note: The original concept for the show wasn’t about gangs at all. It was about an Irish Catholic family and a Jewish family, and would have been set during the Easter and Passover season. Also, WSS could have been called “Gangway!”, so we dodged at least one bullet there.

  • (…I think I’ve officially “I’ll be brief”-ed myself.)

  • In his discussion of the piece in Finishing the Hat, Sondheim confesses he was originally dubious about putting a comic song (“Gee Officer Krupke”) in Act II, after two murders end the first act. Apparently, Bernstein and Laurents cited the porter scene in “Macbeth” to point to the uses of comedy mid-drama. (In the film, “Krupke” and “Cool” are swapped.) He also talks a bit about the purposeful choice of when/with which characters to use simpler, more poetic languages, and when to use more stylized “street talk,” and how in some ways it mirrors choices between poetry and prose in the Shakespearean version.


  • The original Broadway cast doing the dance break from “Cool” on the Ed Sullivan Show

  • The “Dance at the Gym” sequence from the 2009 revival, because you can never have too much Karen Olivo in your life

  • This video essay is technically about the film version, but it’s mostly a really cool discussion of the music theory underpinning the score, including Bernstein’s extensive use of tritones


Year: 1968

Written by: book and lyrics by Gerome Ragni and James Rado; music by Galt MacDermot

Shakespeare connection: While not directly based on a Shakespeare play, Hair draws parallels between its protagonist and Hamlet both thematically and by overtly quoting the play.

It may seem like a stretch to include Hair in this list, but any musical that sets the “What a piece of work is man” speech to music deserves a seat at the table. (The finale also incorporates some lines from Romeo and Juliet.) Hair is fairly loosely plotted, but the main through-line focuses on Claude’s indecision about whether to flee in the face of being drafted for the Vietnam War. Claude is tied to Hamlet directly (he quotes “O, that this too, too solid flesh would melt”) and indirectly (his big solo at the end of Act I, “Where Do I Go?” echoes the “To be or not to be” soliloquy). Instead of a show that’s a direct adaptation of a Shakespearean play, Hair is one that uses Shakespearean references to shape and comment upon its own subject matter.


The setting of “What a piece of work is man” follows and contrasts with a drug trip vision of war carnage. In most staging, the stage is littered with bodies during the duet. The Shakespearean text in the finale also strongly suggests Claude ultimately dies in Vietnam. (Many productions make this explicit by covering him with a black cloth or otherwise confirming his death visually.)

Shakespearean side note: Composer Galt MacDermot went on to collaborate on a rock musical version of Two Gentlemen of Verona. It’s now mostly forgotten except among people salty that it beat Follies for the Best Musical Tony Award in 1971.


  • The original cast at the 1969 Tony Awards (cw for use of the n-word and lyrics explicitly about violence/warfare)

  • “Theater Talk” interview with James Rado, Galt MacDermot and Gavin Creel (who played Claude in the 2009 revival and looks approximately 12 years old in this interview). Also includes Creel (and Rado) singing “Where Do I Go?” (at 21:45)

Love’s Labour’s Lost

Year: 2013

Written by: music and lyrics by Michael Friedman; book by Alex Timbers

Shakespeare connection: A modern musical version of the play of the same name.

The Public Theater’s Shakespeare in the Park in NYC usually includes two shows (formerly in repertory, now more often sequentially). In 2013, they did a fairly classic rendition of The Comedy of Errors first and then let Michael Friedman and Alex Timbers, who’d previously collaborated on Bloody Bloody Andrew Jackson, loose on Love’s Labour’s Lost. The resulting 90-minute musical is fairly faithful to the plot of Shakespeare’s original, but sets the action at a modern-day five-year college reunion. The show uses a mix of the play’s original language and very contemporary language in both the spoken dialogue and the lyrics, which seems weird, but worked for me! (You can get a sense of this especially in “Are You a Man?” on the playlist.) They also made the clowns funny largely by just casting Rachel Dratch as one of them. (That’s... semi-editorial, but also Friedman says more or less the same thing in an interview.) The tone is both very knowing and very warm, and the modern setting allowed for some self-referential winks that people who know BBAJ wouldn’t be shocked by. (A delightful surprise seeing it live was the moment Ferdinand, Berowne, Longueville, and Dumaine broke into a cover of Mr. Big’s “To Be With You.” Yes, it is on the cast recording.) It didn’t make it to Broadway, for possibly self-evident reasons — it’s a bit high-concept and it’s not a play a lot of people are clamoring to see an adaptation of — but the cast recording is still available to delight you. I hope some colleges are doing it.


Twelfth Night

Year: 2018

Written by: music and lyrics by Shaina Taub; book by William Shakespeare

Shakespeare connection: As the title suggests, it’s a musical version of Twelfth Night.

Twelfth Night may be the most musicalized Shakespeare play. I know of at least six besides this one: “Illyria” from 2002, “What You Will” from 2001, “A Rock n Roll Twelfth Night” from 1997, “Love and Let Love” from 1968, “Music Is” from 1968, and “Your Own Thing,” also from 1968. (No, I don’t know what was going on in 1968.) In addition, two separate jukebox musicals hung their hat on Twelfth Night for their framing stories: “Play On” in 1997, which used the music of Duke Ellington, and “All Shook Up” in 2005, which was an Elvis show.

I picked Shaina Taub’s version for two simple reasons: Its cast recording is available for streaming and it’s very, very fun. I also recommend the original concept album, which is available on Bandcamp.

The 2018 version is a partial “reimagining” of an earlier 2016 production. Taub also musicalized As You Like It in 2017. Both shows were originally designed for brief runs with large casts of mixed professional and amateur performers, and Twelfth Night kept this conceit (in modified form) for its longer run. The amateurs appear as the chorus on the recording. (As You Like It was supposed to get an full mounting this summer the way that Twelfth Night did in 2018, but… 2020 happened.) Much like Love’s Labour’s Lost, Twelfth Night marries modern language and the original text, but instead of blending them in both book scenes and songs, Twelfth Night clearly delineates: spoken is Shakespare, sung is Taub. The show’s design is semi-modern too, though it's clearly not meant to be particularly grounded in reality. (A lot of reviews used the word “whimsical.”) Also! Poor Antonio finally gets included in the happy ending, though your mileage may vary on how satisfying you find the way he does. The show is a little twee for some tastes, but I find it enormous fun, despite some nitpicks, and I hope it gets an extended run at some point.


Honorable Mentions:

  • The Fantasticks (1960) – A musical that’s very much about theater/being a play could hardly leave out Shakespeare. The plot consciously echoes parts of Romeo and Juliet and A Midsummer Night’s Dream. It also includes a character who variously quotes Julius Caesar, Hamlet and Henry V. (Cw if you listen to the original cast recording/read the original libretto: This show originally used the word “rape,” repeatedly and at length, in the sense of an abduction rather than a sexual assault. If you listen to the original cast recording, be aware of this fact, especially going into “It Depends on What You Pay.” This song has been replaced by a different one, for probably obvious reasons if you’ve listened to it, in current productions and the 1995 film.)

  • The Lion King (1997) – As you may have heard, this one is loosely based on Hamlet.

  • Something Rotten (2015) – This show wasn’t my jam, but a lot of my friends deeply enjoyed it. A musical comedy about fictional brothers who anachronistically invent the musical to compete with Shakespeare’s popularity.

  • Scotland, PA (2019) – I didn’t make it to this before it closed, but friends told me it was delightful. Hoping for another production when live theater exists again. A musical based off the movie of the same name, which is an adaptation of Macbeth.



- “Broadway Musicals, Show By Show” (Stanley Green and Kay Green/Cary Ginell)

- and

- “From Assassins to West Side Story” (Scott Miller); “Rebels with Applause” (Miller) also has a chapter on “Hair” “The House That George Built: With a Little Help from Irving, Cole, and a Crew of About Fifty” (Wilfrid Sheed) – chapters on both Richard Rodgers and Cole Porter

- Broadway: The American Musical (documentary series)








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