A Definitive Ranking of Musicals by Stephen Sondheim, by Someone with a Degree in Theater and Too Much Time on His Hands

It’s been a while since I wrote a blog post that had nothing to do with how sad I am during a world-historical pandemic, and since I can’t stop singing “Losing My Mind” in the shower these days, here you go:

1. Sunday in the Park with George

Look, even with that absolute mess of a second act, there’s no way Sunday couldn’t top the list. It’s Sondheim at the peak of his songwriting ability, capable of achingly beautiful melody (“Sunday”) and bulletproof wordplay (“Putting It Together”). The pointillist score is perfection, and even with the lopsided acts, it remains one of the theater’s definitive statements on the tragedy that is attempting to create (“Finishing the Hat”). Plus any show with Bernadette Peters has to make the top five; the woman put out an album called Sondheim, Etc. and then had the brilliance to title the b-sides Sondheim, Etc., Etc..

2. Sweeney Todd

Certainly Sondheim’s most cohesive show, this is the one that hooked me to the artform at thirteen, which is coincidentally the exact right age to listen to Sweeney Todd. The score is inarguably brilliant, if a bit self-consciously so: Sondheim seems to have pulled a bit of a prog rock here and written in strange keys and time signatures just for the hell of it. Still, the Grand Guignol does not disappoint, from buckets of blood (most of the second act) to some of the best/worst puns committed to musical theater (“A Little Priest”).

3. Into the Woods

Like Sunday, this is a highly conceptual show with a clearly delineated first and second act. Sondheim and his collaborator James Lapine do a better job with this structure, delivering both send-ups of a Disney-style fairy tale (“Opening,” “A Very Nice Prince”) and its hollowed-out shell (“Last Midnight,” “No One Is Alone”). In many ways Sondheim’s darkest show, in which we can detect the shadow both of AIDS and his unhappy childhood.

4. A Little Night Music

We’re gonna get a lot of high concepts, since this is the 1970s and 1980s after all: A Little Night Music decides to do the whole thing in waltz-time, though it cheats a bit in places (“A Weekend in the Country” runs in 12/8, effectively feeling out common time). “Send in the Clowns” is better than its reputation suggests, though I’ve always had a soft spot for “The Miller’s Son,” one of the rare times that Sondheim permits a character who likes to fuck and isn’t sad about that to exist.

5. Passion

Speaking of characters who like to fuck and are very sad about that! Passion’s a weird one, probably the last fully-formed Sondheim show, setting aside the bumptious journey of Road Show. Passion finds Sondheim’s composing at its most abstract, with nary a melody or coherent “aria” to be found. Still, there’s something I find enormously compelling about the show, which feels like a composer understanding that while he had probably passed his peak, that means it’s time to take the gloves off and deliver something completely uncompromising.

6. Assassins

Assassins is a deeply silly show. The idea of a revue of American assassinations is just a shade too high-concept, and feels a bit like it’s designed to appeal mostly to edgy closeted teens (*cough* *cough*). Nevertheless, this is Sondheim’s chance to flex his pastiche muscles, something that rarely comes to the fore so explicitly in his previous shows. Highlights include the barbershop quartet of “The Gun Song” and the bizarre cakewalk of “The Ballad of Guiteau.”

7. Pacific Overtures

“Someone in a Tree.” It’s Sondheim’s best song, a moving theory of history compressed into a seven-and-a-half minute slow build. Pity that the rest of the show is a bit of an Orientalist mess. I have a lot of love for the individual songs, but it’s hopelessly mired in its time. Perhaps it could use a re-write to bring out some of its pathos, but as it stands it’s difficult to get past the Japan-is-going-to-take-over-the-world vibe of the second act. That being said “A Bowler Hat” is probably his most affecting song, itself a three-act play that rivals, in miniature, more sprawling attempts like “Chrysanthemum Tea.”

8. Anyone Can Whistle

I deeply admire this show, one of Sondheim’s earliest. It’s a giant mess, but in the way that we should all have the chance to be. The songs sprawl out into massive setpieces (“Simple”), the plot makes less than no sense, and if you listen to the original recording, you get the treat of a rapping Angela Landsbury (“Me and My Town”).

9. Follies

The music is some of his most sophisticated, although it falls into the trap of some of his later shows of having two acts that don’t quite work well together. A pastiche show, like Assassins, Follies recreates the Ziegfield variety with much aplomb, although it feels more like a running variety show than anything with a coherent spine. Probably Sondheim’s best standalone songs, particularly for the women: “Losing My Mind,” “Would I Leave You?” and “I’m Still Here” are unalloyed classics.

10. Company

I’m very mixed on Company. I don’t think it’s bad, just tremendously dated, and not in a way that’s easy to rescue fifty years later. The individual songs can be wonderful, although one gets the feeling it’s a bit too self-conscious about how it’s New and Important Musical Theater (sorry, “Marry Me a Little”). “The Ladies Who Lunch” is obviously a classic, but I feel more that’s on Elaine Stritch than Sondheim—no one since has quite had the balls to be so off-key in a Sondheim show and be proud of it.

11. Merrily We Roll Along

The most high-concept of them all, and one I’ve only heard once so I’m not quite sure what to do with it. It’s remembered mostly as a total flop, and I don’t know if it deserves it, but it’s certainly among the least memorable of Sondheim’s shows, to the extent that I can’t even remember the names of any of the songs lol.

12. A Funny Thing Happened on the Way to the Forum

Okay look, it’s funny enough! But there’s not really like, a lot of music in it? (Five songs in the whole damn second act.) The opposite of Merrily in that it was a huge success, but similar in that I find it generally forgettable.

n/a. Saturday Night, Evening Primrose, The Frogs, Road Show

I actually just don’t know these shows enough to levy a judgment lol, be satisfied with all the free #content you have thus far received.

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