The following list could be a maelstrom, considering the subjectivity of the category. Indeed, choosing my ten favorite Sondheim songs is an absurdly "Sophie's Choice" task.
I've decided to base the list on songs that work out of context — a tall order given Sondheim's mastery of crafting music and lyrics specifically tailored to the characters and situations within his musicals.
That means many of his greatest songs are too tied to those characters and situations to be enjoyable outside those contexts, and therefore are ineligible for this list.
This is especially true of songs from the musicals Sondheim wrote with James Lapine — Sunday in the Park With George, Into the Woods and Passion. This also tends to eliminate bigger production numbers or e duets, although some of those made this list.
10. "You Could Drive A Person Crazy"
In some ways, "You Could Drive A Person Crazy" is the quintessential Sondheim song. The music evokes a particular movement in pop culture, perfectly embodying it while simultaneously turning it on its head — in this case the girl groups of the Andrews Sisters era. The lyrics make use of this almost dizzily bouncy, almost deliriously cheerful aesthetic to disarm the listener in a monologue that is first fun, then cutting, and surprisingly vulnerable. Yes, monologue. Sondheim songs, even terrific out-of-context numbers like "You Could Drive A Person Crazy," always function dramatically as words out of the character's mouth.
It's been a few decades since anyone has seriously pushed the notion that Sondheim's songs aren't melodic. The truth is that Sondheim's music is composed to further a dramatic moment, not to hook ‘em on the pop charts. Oftentimes, when I would hear the "not melodic" complaint, I would want to play people "Johanna" from Sweeney Todd. This stirring, soaring paean has me melting from the first measure of mellifluous music.
8. "Now You Know"
It's harder for group production numbers featuring multiple characters to work outside the musicals they were written for, but "Now You Know" from Merrily We Roll Along is one that does. Don't believe me? Listen to Betty Buckley's terrific rendition on her "Live at Carnegie Hall" album. For the one thing, the issues being addressed in this deceptively buoyant song are universal quandaries relatable for everybody, and the sort of congregational call-and-response style means that the back-and-forth lyrics make sense without knowing the plot of the show. "Now You Know" is a song like no other, offering a unique vision for a life, "letting go your illusions" and still "rolling along."
7. "Anyone Can Whistle"
Did I say "You Could Drive A Person Crazy" was the quintessential Sondheim song? I take it back! "Anyone Can Whistle" is the quintessential Sondheim song, and another one that bucks bogus generalizations once erroneously lobbed at his work — that his songs are hard, cold, urbane and lacking in feeling. On the contrary, it's difficult to listen to "Anyone Can Whistle" without hearing nakedly personal confession from the (then) young songwriter struggling to reach out beyond his limitations. It's a perfect metaphor and its rich poetry is set to a yearning tune. You hear it once and you understand it completely. Listen to it a hundred times and there's still more to ponder.
6. "Another Hundred People"
Company is a musical about life in the big city, and "Another Hundred People" captures that experience vividly. The lyrics make it something of a patter song as they rush, scrambling to extol the myriad social experiences that fly by in metropolitan life, repeatedly accentuating the overwhelming quantity of it all in the titular phrase "another hundred people." Then, as the instrumental accompaniment (be it orchestral or only piano) rushes on, the chorus-ish section of the lyrics slow down for a brief, breathless repose, a glimmer of the serenity, the much needed sleep you may finally find in Manhattan after all the bars are closed and even the drunks on the street have stumbled off to crash somewhere. Only Sondheim could write a song both so busy and beautiful.
5. "Losing My Mind"
"Losing My Mind" is another Sondheim song written in the style of a particular pop song genre — in this case the torch songs of the 1930s. But somehow, through the richness of Sondheim's words and the depth of feeling they portray, you might be moved by "Losing My Mind," even if you're not a fan of torch songs of the 1930s. The lyrics offer a ride on romantic obsession's irresistibly slippery slope from the everyday coffee cup and afternoon chores to questioning one's own sanity. It ain't pretty, but god, is it pretty. And the second time through, after the instrumental interlude, when the stakes are raised and the singer's voice is at full throttle, "Losing My Mind" is absolutely thrilling.
4. "Not A Day Goes By"
Sondheim's songs are so compelling that I find myself thinking of him, the artist behind the song, much the way one does with popular singer-songwriters and rock/pop stars. With so many Sondheim songs written in various musical styles, it's hard to identify the sound of Sondheim. Songs from Merrily We Roll Along seem to be good candidates for this because it's a Sondheim show about characters of his own era, the second half of the 20th century. The same is true of Company, although as I've said, I think that show is musically stylized to paint an aural portrait of city life. There are many great songs in Merrily We Roll Along, but the gorgeous, poignant "Not A Day Goes By" stands out. If Stephen Sondheim is my pop star, then "Not A Day Goes By" is his chart-topping power ballad.
3. "Not While I'm Around"
"Not While I'm Around" is so sweet and so seemingly simple, it's easy to forget its origins. When Toby sings to Mrs. Lovett of demons prowling everywhere nowadays, he means specifically today, like Sweeney Todd upstairs slitting people's throats. Indeed, his promise that, "nothing's gonna harm you, not while [he's] around," is in light of a very real danger that he may not be around, should he fall out of favor with Sweeney (which he indeed he does, although it's his own mettle that is proven when he kills Sweeney in the show's final moment). Sentiments like these might be tossed around tritely in countless other ballads, but the dire straits that inspire them in Sweeney Todd make for a song sweet and simple, yes, but also with great depth and integrity. That's why "Not While I'm Around" comes across not as syrupy and saccharine, but as real and felt.
2. "Broadway Baby"
"Broadway Baby" is so irresistibly tuneful and fetchingly witty, the first time you hear it, you swear you've known it all your life. Sondheim's pastiche of those feisty, hearty, old toe-tappers (like "Broadway Rhythm") is almost indistinguishable from the original songs themselves, similarly revealing, beneath a sunny exterior, a relentless ambition for show business success. What makes "Broadway Baby" different is that the song itself is a comment on keeping up the cheerful appearance while maneuvering toward fame. So Sondheim gives us a song that works perfectly as what it seems to be and can also be turned inside out. You're enjoying this broad belting out this number, while at the same time thinking about what is says about her life that she's doing it, which is then making you enjoy her doing it even more. Whoa.
1. "Send In The Clowns"
I hesitated to include "Send In The Clowns" at all, let alone as the #1 Sondheim song, but ultimately I'm paying homage to the fact that on a list of Sondheim songs that work out of context, you can't argue with the track record of "Send In The Clowns." After debuting in A Little Night Music in 1973, "Send In The Clowns" was a legitimate pop hit for both Frank Sinatra and Judy Collins (on the pop charts twice for the latter). The song has been so ubiquitous in popular culture that when Krusty the Clown sang it on "The Simpsons," millions of American school-age children thought not, "What is this strange, sophisticated Sondheim aesthetic unfamiliar to my young ears?" but rather, "Oh, that old chestnut." And the reason is clear. Lots of songwriters go for the jugular for effect, but Sondheim only goes there when it's integral to the story he's telling, and that makes all the difference. The result is heartbreaking.