I don’t think my hesitancy around show tunes and musicals is unique. For a long time, I associated musical theater with Disney movies and classics like Annie and The Wizard of Oz. I found their treacly optimism sickening, their themes — redemption through romantic love, the centrality of family, the importance of virtue, the final victory of the good guy over the bad — tired. I wasn’t interested in what felt like pure artifice with no tether to reality. I thought the sparkly perfection of the singing-and-dancing performances was too much a product of the practical need for musicals to succeed commercially, to become hits. I’d lose patience when I felt songs didn’t push the plot forward, and half the time I didn’t care what happened to the characters. I didn’t want a hero, and I didn’t want to feel righteous along with him, and I didn’t want to learn a neat little lesson at the end.

Luckily for me, neither did Stephen Sondheim. Sondheim pushed musical theater into a new era, breaking it out of peddling old-fashioned family values and fantasies about romantic love to instead explore darker, realer themes, to introduce characters who don’t get a happy ending, who learn their lesson but only after two acts of struggle, who maybe don’t learn their lesson at all.

One of his more well-known works, Company, reaches its resolution not when Robert, the central character who laments that he’s turning thirty-five and still has never been in love, finally finds The One, but when he fully realizes exactly what it is that he wants: not the just-right-glass-slipper love of fairy tales, but the often excessive, demanding, mortifying love of real life. “Somebody need me too much / Somebody know me too well,” he pleads in the show’s climactic tune, “Being Alive.”

Sondheim’s depiction of real, adult love is more complicated than facile feelings of unbridled happiness and optimism that everything will be okay holding the hand of your One True Love. True love is a challenge to which Robert will have to rise.

When “Being Alive” finally gets to its bridge, we feel all of love’s complications at the same time: the destabilizing force of intimacy (“make me confused”), that feeling of being made fun of when someone shows us just how well they know us (“mock me with praise”), the complicated desire to be reduced to an object in the service of another (“let me be used”), the possibility of magic in the quotidian (“vary my days”). Then, at the very end, when he’s finished pleading for what he wants, he takes responsibility for his own part: “I’ll always be there / as frightened as you / to help us survive / being alive.”

Much of Sondheim’s work is similarly about trying to find true connection in an alienating world. In Follies, two former showgirls reunite, years after their prime, to find that they are both in unhappy marriages and that one is in love with the other’s husband. “You said you loved me, or were you just being kind?” Sally sings, but it’s not lament — she’s really trying to figure it out.

In Merrily We Roll Along, a show whose initial run lasted only sixteen shows and whose negative critical reception made Sondheim announce he was leaving musical theater, Beth sings to Frank as they’re divorcing, “You’re somewhere a part of my life / and it looks like you’ll stay.” She goes on, “I keep thinking when does it end? / Where’s the day I’ll have started forgetting?”

Assassins, a show that explores the motivations of nine people who either assassinated or attempted to assassinate an American president, concludes that more than acting out of any particular political conviction, its protagonists just wanted to feel like their lives mattered, like they were connected to something in the world, like their actions had some impact. But while Assassins sympathizes with its characters, it also admonishes them for their selfishness. Its final number, a reprise of its first, takes the all-American belief in individual freedom to its logical, sinister conclusion: “Everybody’s got the right to their dreams,” the assassins sing — even when that dream is to murder the head of state.

Sondheim wasn’t interested in the happy ending, in the hero’s lone journey. He eschewed the sorts of plots that can make plays and musicals feel cut through by a unidirectional arrow propelling the viewer toward a big, singular goal. He knew life was much bigger than that. What happens after we get, or don’t get, what we think we want? The moment when the curtain closes on most other musicals is the moment when Sondheim’s opened.

His breaking with convention and experimentation make it difficult not to think of him as a singular, lone genius. I read once that he liked to compose while lying down, creating an image in my mind of him alone on a sofa, sheet music propped up on a cushion, pen hanging out of his mouth.

Such a photo of Sondheim exists, but there are many more that capture the opposite of that sort of solitary act of creation: Sondheim at a piano, surrounded by a gaggle of singers; Sondheim next to longtime collaborator James Lapine, laboring over a score; Sondheim discussing how to record Sunday in the Park with George with Bernadette Peters, who is standing on the stage’s edge, leaning over, hands on her knees so she can be at eye level with him. Every score, every song, every lyric, every harmony, every melody needed Sondheim to write it just as much as it needed singers to sing it, musicians to play it, producers to record it — and life to inspire it.

Sunday in the Park with George, which won the 1985 Pulitzer Prize for Drama, illustrates this best. Georges Seurat watches people in his life come and go, make decisions without him, and ultimately leave him behind as he pursues his craft. At the end of “Finishing the Hat,” Georges, played in the original production by a tall and bearded Mandy Patinkin, holds out his paper pad and exclaims: “Look! I made a hat! Where there never was a hat!”

The scene captures a moment that feels both momentous and trivial: You’ve finished something, made something that didn’t exist before, something perhaps better than anything else you’ve ever made. But also, it’s just a hat.

It’s the loneliest song in a show that wrestles with the duty of the artist to interpret life, the solitude needed to do the work of interpretation, and the interaction needed to have anything to interpret in the first place — and then to understand whether what you’ve interpreted has meaning to anyone other than you.

Sunday in the Park with George explains Sondheim himself as an artist, especially if we understand George to be his stand-in. But it also explains us to ourselves, artists or not. We wrestle with our place in the world, our relationship to ourselves and to other people; we “want to know how to get through . . . to something new, something of [our] own,” like George sings in Sunday’s penultimate number, “Move On.” We alone can live our individual lives, but we never do it in true isolation from other people. If we’re lucky and if we’re open to it, we find companionship and encouragement like Georges finds in Dot, who tells him “anything you do / let it come from you / then it will be new.”

There’s no neat little ending to Sunday in the Park with George. Instead, the musical ends with a reprise of its largest, most sweeping song: “Sunday.” As “Sunday” swells, the company’s harmonies huge and soaring, we understand that this is life, too: abundant, enormous, lacking in tidy conclusions and full instead of a perpetual opening up of “so many possibilities.”

It would be too easy to say that the same is true of Sondheim’s life and work, but it is. There’s a reason they call the restaging of a play a “revival.” The magic of theater is that a musical can live forever, brought to life by groups of people, again and again refreshed and renewed. It took Sondheim to make these songs, and it will take hundreds of people for them to ever reach us and move us. No one, to borrow from the penultimate number in Into the Woods, is alone.