Sondheim is (rightfully) regarded as one of the greatest masters of modern musical composing. It seems like he can take what seems to be a terrible idea and make a masterpiece out of them...
  1. Two bachelors in NYC try to find dates for Saturday night.
    Saturday Night (1954) -This took 43 years to be produced and probably will not be remembered as fondly as some of the later works. We are off to a great start since this is the one show I know very little about.
  2. A street gang made up of ballet dancers tell a "modern" version of Romeo and Juliet where the language was already dated by the time it opened.
    West Side Story (1957)
  3. The story of a monstrous mother's neglect on a young girl who ends up being pushed into a life as a stripper.
    Gypsy (1959)
  4. Ancient Greece: The Musical Comedy!
    A Funny Thing Happened On The Way To The Forum (1962)
  5. A woman who runs an insane asylum gets seduced by a con man who may or may not be one of the escaped members of the insane asylum. There is also a villainous Mayoress played by Angela Lansbury who at this point has never sung a single note in her whole life. Honestly I've seen a wonderful production of this and still don't quite know what happens.
    Anyone Can Whistle (1964)
  6. A musical written by Richard Rodgers without lyrics by Oscar Hammerstein.
    Do I Hear a Waltz (1965)
  7. Plot? We don't need to no stinking plot. A series of vignettes about a man having an early mid-life crisis as he is about to turn 35 and remains unmarried.
    Company (1970)
  8. A bunch of old ladies get together in an old theater that is about to be torn down. Instead of any real confrontation of the central conflict, each of the four main characters will lament individually about their problems in pastiche Follies/Vaudeville numbers as a climax.
    Follies (1971)
  9. It's 1973 and the disco era is revving up. You know what audiences want to hear in their music: a good ol' 3/4 waltz. Let's do that for the entire show.
    A Little Night Music (1973)
  10. A musical based on a Ancient Greek play performed in a public swimming pool.
    The Frogs (1974)
  11. A musical telling of westernization in Japan. Written by a white American.
    Pacific Overtures (1976)
  12. A vengeful barber conspired with his obsessive neighbor to bake his victims into meat pies. Also featuring a masturbating judge, boring lovers, and a slave boy named Toby.
    Sweeney Todd (1979)
  13. A musical about three best friends falling apart told in reverse chronological order. Do you think this will be confusing? Nah, just throw a jaunty overture at the top and people will love it!
    Merrily We Roll Along (1981)
  14. A musical that examines the characters in a painting you've probably only seen if you live in Chicago. In a fun twist, Act Two jumps forward to the present day as we follow the great grandson of the protagonist from Act One. But then at the end his great-grandmother's ghost hits on him thinking that he is his great-grandfather.
    Sunday in the Park with George (1984)
  15. A mashup of fairy tale characters you loved as a kid. But they are all going to get raped or murdered. Also the two main characters are made up and not from any real fairy tale.
    Into the Woods (1987)
  16. Remember how much people hate John Wilkes Booth and Lee Harvey Oswald? Well let's tell THEIR side of the story! While we are at it, let's throw in anyone who has ever assassinated (or attempted to assassinate) a president.
    Assassins (1990)
  17. The story of a hideous woman who has no personality beside being really really sad somehow makes an attractive man (who has a BOMBSHELL of a lover back home) fall in love with her.
    Passion (1994)
  18. A story about two real life crooks who you've never heard of as they go to Alaska to find gold and Florida to find real estate.
    Gold/Wise Guys/Bounce (2003)/Road Show (2008)