Sondheim Musicals, Ranked

(Only shows where he was both composer and lyricist. So no Gypsy or West Side Story. Not enough room to dive into librettists but credit to Lapine, Furth, Wheeler, etc. Top 5 get detailed breakdown.)
  1. 1.
    Sunday in the Park with George
    "Look I made a hat." Sondheim's take on Georges Seurat is his masterpiece and in my opinion the single greatest musical of all time. No other piece of art more expertly deals with the price and process of making art. It's a love story that you think is between two people but ends up being between an artist and his creation. Its second act seems crazy on paper but in context works perfectly. Initially it may seem difficult and inaccessible but in time it opens itself up to you. It's worth it.
  2. 2.
    Company
    "Somebody hold me too close." Sondheim's exploration of a bachelor who has the competing interests of wanting to settle down and get married while also loving being able to fuck lots of beautiful women is a sad, lovely, relatable musical that could easily come off as a tone deaf "aww it's so hard to be a hot manwhore" disaster and yet somehow doesn't. Thankfully the definitive production with Raul Esparza and directed by John Doyle was professionally filmed and you can watch it right now.
  3. 3.
    Into The Woods
    "Maybe they're really magic." The movie doesn't do this justice unless you know and love the original and can fill in the abridgments in your head. A show that reminds us that happy endings are rarely the end and even our heroes can do bad things and stay worthy of our love, Into The Woods is a Trojan horse. On the surface it's an attractive, accessible fractured fairytale. But if you go deeper you'll find it's a complicated look at complicated people... Some of whom just happen to be magical.
  4. 4.
    Sweeney Todd
    "Nothing's gonna harm you." It's just your classic tale of a barber and his neighbor who kill people and bake them into pies. The score is lush and thrilling and scary and funny. A tale of how revenge will corrupt and will often make you lose sight of what it is you were really after in the first place has no business being as fun as Sweeney is.
  5. 5.
    Merrily We Roll Along
    "Something is coming." Sondheim's delightful mess. Told in reverse chronology, no major production has quite found a way to make this one work. But that's what makes it so fascinating. The songs are incredible, some of Sondheim's best. And the tale of three idealistic kids who grow up to be jaded by the world, when told backwards does pack an emotional punch. But it usually ends up feeling messy. A reminder that our heroes fail sometimes but that some failures are still brilliant.
  6. 6.
    Assassins
  7. 7.
    Follies
  8. 8.
    A Little Night Music
  9. 9.
    Pacific Overtures
  10. 10.
    A Funny Thing Happened on the Way to the Forum
  11. 11.
    Road Show
  12. 12.
    Saturday Night
  13. 13.
    The Frogs
  14. 14.
    Anyone Can Whistle
  15. 15.
    Passion