Photo-Illustration: Vulture

What is the modern American musical theater? What are its best songs? When does it even most properly begin? Must we now divide everything into “Before Hamilton” and “After Hamilton,” as with the birth of Jesus Christ himself? Phantom of the Opera is still running — would “Before Phantom” and “After Phantom” be more appropriate? Is there even one genuinely good song in Phantom? How much Sondheim can you cram into a listicle before even your most dedicated base gets restless? And were there more than three good new musicals on Broadway in the whole of the 1990s? These questions, along with many others, were the ones I asked myself as I sat down to write this list.

Why only the past 40 years? Why not the best show tunes of all time? Well, first of all, because Broadway has been around since the late 19th century, and I’m only one small human being (no matter what Eric Trump might say) and human beings tend to function best within fathomable limits. And also, the past 40 years encapsulate the post-Vietnam era, on Broadway no less than in America itself, and have brought us to our present state of societal and emotional collapse: the cynical Weimar-like decadence of the late ’70s (and also, Annie); the greed, bombast, and conservatism of the ’80s (and the quiet intellectual resistance that sprung up in reaction to it); the AIDS crisis, which devastated New York City, and the Broadway community in particular; the wholesome commercialism of the ’90s and the Disneyfication of Times Square (a cultural phenomenon that, while for many regrettable, is nonetheless important enough that I decided to make eligible songs that originated in Disney movies before turning up on the Great White Way); the confusion and vague paranoia of the early aughts, in a city still reeling in the aftermath of 9/11, and the optimistic, tolerant multiculturalism of the Obama years, which now feels as though it was all an impossible dream, the way it must have to listen to the original soundtrack of Camelot during the Nixon administration.

So that seemed like plenty, and what eventually came out is a list that is deeply personal, probably idiosyncratic, and certainly may not please everyone. I don’t apologize for this (although I do apologize for having never seen, or even listened to, The Light in the Piazza. I’m sure I’ll hear about that, and I know exactly from whom). Because that’s what the musical theater is: a deeply personal, deeply ingrained identification that is often formed early in childhood and never lets go. Different songs mean different things to you at different times in your life; other songs drive you crazy but you find yourself powerless to deny their greatness (and still know every single word. And cry at them, sometimes, when it’s late and you’ve had a couple drinks).

So here are the 30 songs from a few more years than I’ve been around that have meant something to me. And because each of our own realities is finite and definitive, I will say: They are unquestioningly the Greatest 30 Show Tunes of the Past 40 Years. Enjoy, and tell me why I’m wrong in the comments!

A lot of people are a whole lot racist, is my main takeaway from the past year. But that doesn’t detract from the appeal of this plucky charmer about the ubiquity of microaggressions, in that nostalgic time when America actually had the decency to hide its latent bigotry behind a veneer of shame or at least politesse, and if you wanted to say something really outrageous, it was better to have a big fuzzy orange puppet do it for you. (And it still is, come to think of it, except we were all better off when it was John Tartaglia’s hand up his ass instead of Vladimir Putin’s.)

The Venn diagram of Idina Menzel fans and aspiring YouTube tween stars is not so much a diagram as a single solid circle, and without Stephen Schwartz’s (literally) uplifting and defiant ballad of female empowerment, what would they do? (Be stuck singing “Omigod, You Guys” from Legally Blonde over and over again, that’s what.) But what makes “Defying Gravity” such a watershed moment onstage and in song isn’t just the sunny, “You Go Girl #WomenWhoWork” message that women, if they put their minds to it, are unstoppable; it’s the not-so-veiled threat that women, when they put their minds to it, are unstoppable. Wizards everywhere should be very afraid.

Female duets are few and far between on the Broadway stage (“Every Day a Little Death?” “Marry the Man Today?” “If Mama Was Married”? “I Will Never Leave You”? “Defying Gravity,” sort of? Am I disproving my own point?) Anyway. Girls still tend to outnumber boys in any given Broadway-themed voice class, so whenever there’s something great they can sing together, it deserves recognition. Particularly when it’s a number as fierce and feisty as Maureen and Joanne’s unapologetic lovers’ quarrel from Rent. Other songs in the show are more ubiquitous, more sentimental, more imbued with their own sense of grandeur and tragedy and importance — but none of them are this much fun. All this, and it passes the Bechdel test! And, speaking of Bechdel …

… A friend of mine likes to say that the only thing anyone truly wants out of life — or art — is to be seen and understood for who they are. Of course, in order to be seen for who you are, you have to be first shown who you want to be. The gorgeous “Ring of Keys,” from Fun Home, based on Alison Bechdel’s graphic memoir of the same name, manages to capture this precise moment of discovery, when a butch woman walks — no, swaggers — into a luncheonette “with your short hair/And your dungarees/And your ring of keys/Oh oh/Your ring of keys” showing the character based on Bechdel’s yearning younger self a reassuring, exciting — and unapologetically sexy — vision of her future, in what may be one of the most perfect “I Want” songs ever written.

I’m not going to argue about this with you. Bombshell, the show-within-a-show from NBC’s late, lamented Smash is a real Broadway show (although we’re still not sure if Julia Houston a.k.a. my cousin Debra Messing, ever exactly finished the book.) It has been performed, live in concert, with real Broadway actors. If, in our collective alternate dream history, Smash had run for 21 seasons, beating Gunsmoke as the longest-running network television drama in history, it might have actually run on Broadway for real, with Katharine McPhee and Megan Hilty battling it out each night for the title role, or at least alternating like Laura Linney and Cynthia Nixon in The Little Foxes — and then we’d all have to go twice, and there would be fistfights in the lobby over whether Karen or Ivy was the better Marilyn, and Hillary Clinton would be president but she would still show up on opening night to a glorious standing ovation because this would be a world in which the opening of a new Marc Shaiman and Scott Wittman musical on Broadway would be a considered a state occasion. But even in our present bleak reality, “Let Me Be Your Star,” in which Marilyn Monroe pleads with an unseen director/audience/network executive/Satan to grant her fame and fortune in return for her youth, health, and soul is everything you want a big, exciting, aching show biz ballad to be. And for a brief shining moment in the New York City of 2013, it would even occasionally play upon my own late-entrances into a certain kind of dingy late-night piano bar, allowing me to swan across the filthy carpet like Angela Lansbury taking the stage at a long-ago Tony Awards ceremony to the strains of “If He Walked Into My Life.” Nothing has ever made me happier. Nothing.

Around the time Ragtime opened on Broadway, I started as a freshman at NYU. All incoming freshmen that year were required to read the novel the musical was based on, as a way of acquainting us with the history of our adopted city, and the work of its author E.L. Doctorow, who had been named the Official Writer of NYU that year, or something. To make a long and uninteresting story short, the end result was that I wound up seeing the original Broadway production of Ragtime four times. While I certainly worship Audra McDonald as much as any other sentient theatergoing human being (not to mention some who are well beyond sentience) I can’t say the show itself left much of an impression on me, beyond some white dresses and thinking that if it had debuted 15 years earlier, Tateh would definitely have been played by Mandy Patinkin (not that Peter Friedman wasn’t perfectly great). But now that we find ourselves in this reactionary moment, when large swaths of the country seem desperate to return to a time of “women in white, and sturdy young men at the oar,” I find myself listening to this song at least once a week and marveling at how it manages to wistfully empathize with the pull of nostalgia while defiantly — and gorgeously, in Marin Mazzie’s original interpretation — proclaiming how impossible and indeed undesirable it would be to return to a time where “there were no Negroes and there were no immigrants.” We can never go back to before.

24. “Unworthy of Your Love” (Assassins; 1990 Off Broadway; 2004 Broadway)

This melody has the purity of a campfire sing-along, and the obsessiveness of someone who has sublimated their soul so completely to another being that they are literally willing to commit murder on his or her behalf. Which is why it makes perfect sense that this song is the reason I named my dog Charlie, for the sole purpose of singing to him on our long walks around the neighborhood: “I am … nothing/You are/Wind and devil and God, Charlie/Take my blood and my body for your love.” So far, he hasn’t ordered me to kill. Yet.

What, you thought we were going to get through 40 years of musical theater and somehow not talk about Andrew Lloyd Webber? Well, you were wrong, and we’d be remiss if we didn’t give mention to the most — and arguably only — emotionally satisfying song in Sunset Boulevard. Sung by the delusional silent-film legend Norma Desmond as she sets foot on the studio lot for the first time in years, it has many of the issues endemic to the best of Sir ALW’s work — a repetitive, if instantly hummable, melody; lyrics that are, shall we say, not quite elevated — and yet, it manages to so effectively capture the “… early morning magic/And the magic in the making” that characterizes a hushed film set that I’ve never been able to drive through the gates of a Hollywood studio lot without it instantly implanting itself in my head.

Fuck it. Let’s just rip the Andrew Lloyd Webber Band-Aid all off at once. (Lloyd Webber fans, please accept my apologies if my flip tone about his contribution to the theater is hurting your feelings. I know these preferences are created in childhood and often deeply felt. But as our once-great nation is wracked with seemingly irreconcilable divisions that brought us closer to the brink of civil war than any time in over a century, I feel confident that we can put our differences aside for the greater good of the international community, and move forward together with mutual love and respect. Also, if they actually made Andrew Lloyd Webber–themed Band-Aids, not only would I buy them in a second, I might become a self-cutter just to get to use them. Anyway.) Cats is the fourth-longest-running show in Broadway history. “Memory” is its most famous — and you’ll pardon the pun — memorable song. It is the reason that Betty Buckley is famous (and again if you disagree with me on that, just remember — we’re pulling out of the Paris accord, #unity #resist.) It tinkled out of every single musical jewelry box I disappointedly received as a bat mitzvah gift (I’m pretty sure the boys just got money). It is an inarguably important piece of pop-cultural history. Sometimes, 50 million Elvis fans can’t be wrong. You know?

The last, greatest, and most explicit of Andrew Lloyd Webber’s majestic trilogy of songs sung by women who are desperate for the adoration of others. It won’t be easy/You’ll think it strange/When I try to explain how I feel/How I still need your love after all that I’ve done — does it get more nakedly pleading than that? No. It doesn’t get much better either. “Don’t Cry for Me, Argentina” isn’t so much a musical number as a feeling, a pageant of imagery as skillfully constructed and unforgettable as any of the fascist-lite political rallies it re-creates. You can’t even hear the opening bars without the vision of Patti LuPone, beautiful and severe, floating out onto the balcony of the Casa Rosada in that enormous wedding cake of a gown, raising her arms in both mastery and submission to the hordes of adoring peasants (in which I’m including the audience) below. An icon is born.

If you’re the kind of person who hears the word Annie and finds yourself immediately cast into a waking nightmare, in which a band of beaming leather-lunged moppets in red fright wigs starts haranguing you about the New Deal while strange, silent bald men in diamonds glower at you from every corner of the Oval Office — a room in which there are supposed to be no corners — then get “Tomorrow” out of your head and start humming “Maybe” instead. This sweetly melancholic exploration of what a preadolescent orphan really wants, and how they idealize their missing parents, is a poignant and unaffected exploration of the deep sadness at the root of all that forced Depression-era optimism that even the sourest soul — or even a Republican, Oliver — can appreciate.

An underappreciated little gem of a song from a famously underappreciated (in its own time, anyway) show, “Good Thing Going” has never quite gotten the recognition of “Losing My Mind,” “Not a Day Goes By,” or any of Sondheim’s other iconic torch songs. In large part, this is because of its placement in the original production of Merrily itself: as a party piece sung by the lyricist Charley Kringas (Lonny Price) to a group of potential backers, who listen politely, love it, ask him to sing it again, and then proceed to talk-sing over him about their condos and their dinners as he gamely attempts to honor their wishes. But the bittersweet melody is a recurring motif throughout the show for a reason (never let it be said that Sondheim doesn’t recognize it when he’s got something) and the rueful lyrics are all the more powerful for the way a listener — or performer — can personalize them to reflect the end of any important relationship, be it a friendship, a love affair, a professional collaboration, or some potent combination of all three. Just don’t let anyone talk over you while you’re stoically swallowing that lump in your throat.

Sometimes, late at night, when you’re in a certain kind of bar nursing a glass of cheap scotch and feeling very sorry for yourself about, in Frank O’Hara’s words, the catastrophe of your personality, the only thing you want to hear is a wise, deep, female voice — be it Bea Arthur, Dorothy Loudon, or Maggie the waitress at Marie’s Crisis — singing ruefully about the sacrifices she’s made in loving an emotionally and/or physically unavailable man (is he married? Gay? Does he live in New Zealand and refuse to relocate?) with a kind of stoic nobility. When that feeling takes over you — and believe me, it will — this song, by the legendary Alan and Marilyn Bergman from the more or less forgotten musical Ballroom is what you want to hear, one hundred percent of the time.

I’m a sucker for a great character song written for a villainess, and “Poor Unfortunate Souls” is perhaps the greatest example of this underappreciated genre. (See also, Annie, “Little Girls.”) No less an aria of longing than the perennially winsome “Part of Your World,” Ursula the Sea Witch’s statement of intent is the siren song of the woman who wants just a little more than she’ll ever have, and who will stop at nothing to get it. Introduced in the classic Disney film by veteran character actress Pat Carroll, and interpreted since by divas ranging from Sherie Rene Scott (in the 2008 Broadway production) to Tituss Burgess to the late, great Howard Ashman himself, perhaps the as-yet-unannounced actress playing Ursula in the upcoming live-action film will finally bring this small masterpiece to its rightful place in every the repertoire of every brassy cabaret performer who knows better than to underestimate the importance of body language.

There’s no other way to put this: “Our Time” sounds like youth. Golden, ambitious hopeful youth, when we still had dreams and felt energized and attractive enough to achieve them; before we realized that success — even if you get it — never feels like enough, and money — fabulous as it is — only makes you happy to a point, because nothing ever actually makes anyone happy except being young and having your whole life ahead of you. Except because we are old now and Merrily We Roll Along is backwards, we know all this already. But it’s still a great song.

Howard Ashman was dying of AIDS as he wrote Beauty and the Beast with his long time creative partner, the composer Alan Menken, and the scars and stigmatization of the disease are all readily apparent in the unquiet subtext of both the classic 1991 animated film and the 1994 Broadway production that followed it: the Beast, raging in his castle, sure that his “curse” has rendered him grotesque and unlovable; the mob of angry villagers with torches at the door, their fear and ignorance compelling them to destroy what they don’t understand. Yet the beauty of its title song, an instant classic, is to be found in its calm, almost quotidian wisdom and warm, reassuring melody. “Certain as the sun/Rising in the east/Tale as old as time/Song as old as rhyme/Beauty and the Beast.” Human beings will rage, and they will fail, and terrible things will befall them, but the world will still go on, the sun will still rise and set, and people (and beasts of indeterminate species) will continue to tentatively open their hearts and find a kind of peace in each other. Deep down, all anybody — children and adults alike — wants to hear is that everything will ultimately be okay. When you hear “Beauty and the Beast,” you almost believe it will be.

14. “Sunday” (Sunday in the Park With George; 1984)

Perhaps Sondheim’s most beautiful choral song, “Sunday,” which closes both the first and second acts of Sunday in the Park With George, is nothing less than a secular hymn, an ode to the spiritual transformation and hushed sense of the divine that comes from an encounter with a great work of art. The melody shimmers like the bright flecks of paint on Georges Seurat’s canvas; the soaring voices — mostly heard in angelic unison — meld into a flawless sonic rendering of what it means to bring “order to the whole” through “design, composition, tension, balance, light, and harmony.” They seem, like that pure, clean, golden trumpet blast at the end, to come down from Heaven itself, as the characters we have watched squabble, preen, and promenade take their places in eternity. This is music as perfect and precise as the painting it describes.

I’ll be honest: Dreamgirls is not my favorite show, and “And I Am Telling You (I’m Not Going)” is not my favorite song. But to deny this lengthy, soul-wrenching, emotionally volcanic aria of hurt, rage, and need a place among the greatest show tunes of the past four decades is like saying a Category 5 hurricane is just a little gust of harmless wind. “And I Am Telling You” is undeniable, more a cataclysmic force of nature than a composed piece of music, and to sit through it from beginning to end (because I don’t know anyone who’s ever turned it off in the middle, or failed to sit through, say, yet another YouTube showing of Jennifer Holliday’s performance of it at the 1982 Tonys, and if you’ve read this far, don’t even try to tell me that doesn’t happen at the kind of parties you go to) is to experience a catharsis not dissimilar to passing a kidney stone, giving birth, or slitting the throat of the loathed enemy who raped and ruined your wife, stole your daughter, and transported you to a lifetime of hard labor in the Australian colonies (Effie White and Sweeney Todd have a certain amount in common, is what I’m saying). It’s all entirely too much — and it’s not going anywhere.

12. “Wig in a Box” (Hedwig and the Angry Inch; 1998, Off Broadway; 2014 Broadway)

With its jangling ’70s-era glam rock guitars and lyrics paying tribute to the transcendent power of self-reinvention, “Wig in a Box” — whether performed in its original incarnation by the incomparable John Cameron Mitchell, or any of Hedwig’s subsequent big-name stars — isn’t just one of the best Broadway songs of the past 40 years, it’s one of the best pop songs; a potent, sexy hybrid of Jerry Herman and David Bowie. (In fact, I’ve found it’s even possible, in a pinch, to convince a certain kind of musical-averse and somewhat intoxicated straight guy that it actually is David Bowie. We take our small triumphs where we can.) Its actual composer and lyricist is, of course, the remarkable Stephen Trask, who knows it’s possible to feel something and still rock out, without falling for a moment into the kind of morbid emo sentimentality that has made some post-Hedwig rock operas (I won’t name names here) seem like such a chore. This one’s for the misfits and the weirdos who were punk before it was cool — or even safe.

Stephen Sondheim has a rare gift for the ominous love song, and in “Johanna,” the innocent sailor Anthony’s paean to his mysterious and inaccessible yellow-haired love (the same girl whose fate obsesses virtually every male character in the show) is perhaps his most shining example of this subgenre. The dissonant minor chords in the background, the elliptical lyrics, almost sinister in their unbridled passion: “I feel you, Johanna/And one day, I’ll steal you/Till I’m with you then I’m with you there/Buried sweetly in your yellow hair…” all reflect the darkness of a world in which eroticism is inexorably tied up with death, and where, for a woman, to be desired is to be stripped of all agency or power. And yet, when a song is this beautiful, does any of that really matter?

Every song in Les Miz is both great and terrible (often for the same reasons), so what could be greater and more terrible — in the God of the Old Testament kind of way — than “One Day More,” the sprawling ensemble number that manages to incorporate every character and motif of the show into one overwhelming, bombastic, and utterly irresistible Act One finale? It’s got everything the archetypal musical theater universe has to offer — simpering lovers, spurned and complicated women, idealistic young students, comic relief — all rolled into one cacophony of counterpoint, and if that waving red Flag of Freedom at the end doesn’t make you want to avant to the barricades to fight bravely and futilely to the death over … something … you might seriously want to consider your commitment not just to the #Resistance, but to the concept of musical theater itself.

Countless Broadway shows contain some variation on the theme of “Be yourself.” But few deliver that message as powerfully or enduringly as in this ultimate anthem of gay self-acceptance and pride from La Cage Aux Folles. In 1983, as the AIDS crisis was still spoken of in whispers around the West Village, and decades before same-sex marriage was even on the menu, or transgender children and their allies were fighting for visibility and fair treatment in public schools, Jerry Herman put a drag queen center stage in a major Broadway musical and had her triumphantly declare: It’s one life, and there’s no return and no deposit/One life, so it’s time to open up your closet. Generations obeyed. Who says theater can’t change the world?

First, there’s the beat, the one Hairspray’s closing number insistently tells us we will be unable to stop. But here, it’s just starting, bringing us instantly into the irrepressibly plucky psyche of chunky Baltimore sweetheart Tracy Turnblad, as she gets out of bed, gets dressed, and parades through the trash-strewn streets of the city she adores. Maybe it’s the infectious, ’60s-girl-group-inflected melody, or the fact that I too have had the experience of being a dieting teenage girl with big dreams setting off to high school in a somewhat less-than-romantic midsize American city, but any time I hear this song, I can’t get it out of my head for at least a week. Of all the lyrics in what is a decidedly sugarcoated show, it features those that have always seemed to me closest to John Waters’s patented brand of demonic cheeriness, where rats (of both the rodent and hairstyling varieties), flashers, and the civil rights struggle all vie for supremacy in the overheated consciousness of a tubby Tidewater teen. And like I said, there’s that beat.

Let’s face it, Hamilton is an embarrassment of riches. It’s the rare Broadway show that is truly a reinvention of the form, a dazzlingly original work of art that breaks all kinds of previous impassable barriers and will change forever the way we think about musical theater (and its profitability). The score is so inventive, so full of game-changing songs, that choosing a favorite (or even a couple of favorites) is almost impossible, but if I had to name the one that I go back to again and again, I’d pick the heart-pounding opening number. Not just because I’m a sucker for a scene-setting act-opener, or because “Alexander Hamilton” displays more technical prowess or creative inspiration than any other song in the show, but because it’s the moment it all began. When we first hear “How does a bastard, orphan, son of a whore and a Scotsman dropped in the middle of a forgotten spot in the Caribbean/By providence, impoverished, in squalor/Grow up to be a hero and a scholar” we’re like Dorothy stepping into the Technicolor world of Oz, knowing that nothing would never be quite the same again.

Perhaps the funniest, most deftly conceived and sophisticated song ever written about cannibalism — at least, until Lin-Manuel Miranda debuts a hip-hop song cycle about the Donner Party, “A Little Priest” — like all of the best songs in Stephen Sondheim’s Grand Guignol masterpiece, it manages to be a several things at once, a lavishly clever piece of comic relief; a weirdly giddy love song (the yearning excitement with which Mrs. Lovett realizes that she’s pleasing Sweeney Todd, the object of her ardent desire, is one of the most deeply human moments in the show); a trenchant critique of how the dog-eat-dog economic stratification of Victorian England can almost make murder seem like moral imperative: “How gratifying for once to know/That those above will serve those down below.” And for those who think of Stephen Sondheim as some kind of omniscient demigod, how gratifying it is also to know that even He can’t find anything to rhyme with “locksmith.”

5. “Skid Row” (Little Shop of Horrors; 1982 Off Broadway; 2003 Broadway)

Sure, “Suddenly Seymour” is a karaoke classic, and “Somewhere That’s Green” is the kind of ballad beloved by brassy belters looking to show a softer side, but “Skid Row” is the song I always return to in Little Shop of Horrors, the one I never get sick of hearing, and never fails to yield a lyrical delight or harmonic counterpoint that I either forgot about or never noticed before. Not only is it a near-perfect opening number, presaging Alan Menken and Howard Ashman’s unmatched brilliance in establishing the world of a show (seriously, try to imagine the gossipy townspeople and harried merchants of “Belle” from Beauty and Beast without Skid Row’s unstoppable cabs and hopheads flopping in the snow) but it also somehow manages to effortlessly introduce the primary emotional states of the lead characters — Audrey’s wistful desperation; Seymour’s melancholic heroism — making us love them before we’ve even really met them. And there’s still plenty of belting.

The rare song that manages to be both wildly inspirational and mercilessly hilarious, “I Believe,” The Book of Mormon’s anthemic showstopper sung by a newly energized Elder Price, somehow synthesizes the biting and anarchic sense of absurdity of Trey Parker and Matt Stone (and their co-writer, the pre-EGOT Robert Lopez) with the kind of unabashed sentimentality that makes the great American musical truly great — and also, not quite in spite of itself, makes a surprisingly convincing case for the goofy charms of Mormonism: I believe that God lives on a planet called Kolob/I believe that Jesus has his own planet as well/And I believe that the Garden of Eden was in Jackson County, Missouri/I am a Mormon/And a Mormon just believes. All this, and the subtle homage to Fraulein Maria bravely marching through the gates of the von Trapp mansion: “A warlord who shoots people in the face/What’s so scary about that?” which never fails to get a knowing chuckle out of me.

Don’t let the silvery soprano in the ball gown fool you. “On the Steps of the Palace,” Cinderella’s dithering panic spiral of a stunner from Into the Woods, is nothing less than a woke-as-fuck feminist anthem about the male gaze and its corrosive effect on a young woman’s developing sense of self. Who among us hasn’t stood outside a party in slightly limp formalwear, our feet throbbing, wondering whether we are “what a prince would envision” and if so, does that mean we have some sort of unspoken obligation to keep on being that? Is that what we want? Is it impossible to even define what we want because of the limitations society places on its females who have the advantage/misfortune of appearing highly decorative and therefore desirable to powerful men? And will we ever be able to make a decision more empowered and self-actualized than abdicating our agency to a “clue, for example, a shoe” and then seeing “what he’ll do?” Sondheim, to his credit, leaves these questions open-ended. There are no real answers to this eternal problem, except that by the end of the second act, you’d better get it together and be ….

…. “Careful the things you say/Children will listen.” Sondheim is always at his best when he’s at his simplest, framing a profound truth in brief statement of shocking clarity; that good, bad, and in between, your kids are watching you, so pay some goddamn attention. As with all of Sondheim’s best work, it’s a message that resonates in different ways throughout the different states of one’s life: first, as an impressionable child seeing Into the Woods (which solely by nature of its source material is probably Sondheim’s most family-friendly work) on whom it is beginning to dawn that one’s elders are not always entirely infallible; then as a young adult, attempting to make sense of one’s parents’ psyches and the influence they have had on one’s own; and finally as a parent, trying to figure out how to avoid visiting the worst of it on the next generation, all the while knowing that such attempts are likely futile. And for those who like to make a game of catching small glimpses of Sondheim’s own inscrutable soul through his lyrics, consider the anecdote he has frequently repeated to interviewers about the letter his mother, the redoubtable Foxy Sondheim, wrote to him before undergoing a heart operation she assumed she would not survive: “The only regret I have in life is giving you birth.” Then listen to the line: What do you leave to your child when you’re dead?/Only whatever you put in its head” and tell me it doesn’t break your heart. Geniuses have feelings — and mothers — too.

1. “Finishing the Hat” (Sunday in the Park With George; 1984)

The question for me isn’t whether “Finishing the Hat,” Georges Seurat’s tender, soaring, and thrilling artist’s statement from Sunday in the Park With George is the best musical theater song of the past 40 years, it’s whether it’s the best musical theater song of all time. A work of astonishing emotional and melodic complexity about the oppositional forces that run through the life of an artist, “Finishing the Hat” is often cited as Sondheim’s most purely autobiographical song, an assertion that even the famously contrarian master has never particularly bothered to deny (it even provides the inspiration for the titles of his books detailing his artistic process and thoughts on musical theater in general, which are probably the closest thing to a memoir we’ll ever get from him). It also, more than any other work in the Sondheim canon, puts to rest the notion that because of the overriding artistic preoccupation of his career — ambivalence — his output is correspondingly unemotional and cerebral; bizarre, fixed, cold, if you will. Instead, “Finishing the Hat” is Sondheim in full mastery of his most essential truth; that ambivalence rises not from indifference but from a surfeit of caring, from being pulled irresistibly in two directions — in this case, the yearning for love and human connection, and the obsessive need of the artist to create to the exclusion of all else — and knowing, one way or another, you will fail. It’s inspiring, it’s heartbreaking, and it’s true. And it ends with what is perhaps the most succinct yet most eloquent description of the ultimate calling of the artist ever put to page or song: “Look, I made a hat/Where there never was a hat.”