Stephen Sondheim loved puzzles. As a child, seeking solace in the aftermath of his parents’ bitter divorce, puzzles provided him with a much-needed escape. As he described it to his biographer Meryle Secrest, when his parents split, “nothing made sense anymore.” Human beings and their relations were on some level inscrutable, and relying upon them was like building your house on sand. But puzzles had a clear solution: They were dependable; they created some terra firma on which your feet could rest.

Later in life, Sondheim would collect puzzles and games. He subscribed for decades to the Listener, a magazine published by the BBC, specifically for its “cryptic” or “British-style” crosswords—puzzles in which the clues are themselves complex word problems filled with anagrams and puns and complicated wordplay—and then wrote his own versions for New York magazine.

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There’s an alternate universe in which Stephen Sondheim became a mathematician or engineer rather than the greatest musical theater composer/lyricist of all time. As a child, he had little love of art or music and, by his own evaluation, had little visual imagination. But his love of games—in this case, Monopoly—helped him make friends with Jamie Hammerstein, the son of the great lyricist Oscar Hammerstein II, in 1942. “Ockie,” as Sondheim called the elder Hammerstein then, took the boy to see his new musical Oklahoma! when he was 13. Oklahoma! not only set Sondheim on his lifelong career path, but it also established the “book musical”—a musical in which the songs and script work together to tell a coherent and fully integrated story—as the dominant form musical theater would take from then on.

Hammerstein was Sondheim’s first mentor, a surrogate father figure. It was Hammerstein who told Sondheim “to say what you feel, as opposed to what other people feel …  and don’t be ashamed of saying them your own way.” And it was Hammerstein who advised him throughout his early career, giving him crucial—and often very blunt—feedback on his work and telling him to take the job of writing the lyrics for West Side Story, a project about which Sondheim felt intensely ambivalent.

Later in life, Sondheim would frequently speak with disdain about the show that helped establish his reputation. His lyrics were too clever, too flowery, too poetic. They showed off too much. “Lyrics … exist in time,” he told the BBC in 1977. “The audience gets one chance to hear it. … And therefore lyrics must be underwritten but they must be clear. The only sin on the stage as far as I’m concerned is unintelligibility.” But in West Side Story, he had frequently committed this sin. The words didn’t always sit on the music properly, and the rhymes did not exist to call attention to the right words, but to be clever. It was all a big logic puzzle, lacking a human heart. He had approached writing the lyrics the way he had writing his cryptic crosswords. They were an elaborate game, one he would later call “bloodless.”

The problem was that West Side Story lacked characters. As a melodrama, the various people populating the show serve a purely instrumental purpose. Maria and Tony are The Young Lovers; they have few other qualities, few things to base a lyric on. Sondheim was particularly ashamed of their duet “Tonight,” which he felt was a bunch of flowery poetry, signifying nothing. For most of us, the lyrics for West Side Story are the kind of thing that we’d give at least a finger or two to have written. But Sondheim’s relentlessness—his refusal to be satisfied with his work, his desire to solve the puzzle of writing a song that expresses character, theme, and situation, while also sitting properly on sophisticated music—would help make him one of the great artists of any art form of the 20^th century.

His achievement is Shakespearean. Like Shakespeare, he inherited an art form and theater scene from a previous generation, then pushed the boundaries of what theater could do again and again. No one, before or since, has done more to marry the supposedly “low” pop cultural form of the American musical with high modernist complexity and depth, and no one in theater has been more successful in making experimental gambits and aesthetic difficulty appealing and accessible. He’s written a perfect comedy (A Funny Thing Happened on the Way to the Forum) and a perfect romantic drama (A Little Night Music), but he’s also written grand guignol (Sweeney Todd), two largely plotless musicals constructed out of interrelated vignettes (Company, Assassins), a deconstructionist, and quite Freudian, take on fairy tales (Into the Woods), a show that goes backward in time (Merrily We Roll Along), a pointillist take on the creative process (Sunday in the Park With George), and many more.

With Pacific Overtures, Sondheim tackled a historical event, but unlike Fiorello! or 1776 or Hamilton—musicals that relate history as the story of Great Men—Pacific Overtures tells the story of the United States forcing 19^th century Japan to open to trade through the eyes of everyday Japanese citizens witnessing their culture forever change around them. The show’s greatest song (and a personal favorite of Sondheim’s) is “Someone in a Tree,” in which a major meeting between Commodore William Perry and the Shogun’s counselors is recounted through multiple layers of distance. A boy witnessed the event from a hiding place, but he could not hear it. A warrior overheard the conference, but was unable to see it. The boy’s older self also appears, attempting to remember it. The song ends with one of Sondheim’s favorite lyrical devices: a list of small things that, like the unlocking clues of a great puzzle, add up to something much, much larger than they initially appear:

It’s the fragment, not the day

It’s the pebble, not the stream,

It’s the ripple, not the sea

That is happening

Not the building but the beam

Not the garden but the stone

Only cups of tea

And history

And someone in a tree

It’s a device he would repeat again and again, from Into the Woods’ list of potion ingredients, to Company’s lists of all the joys and struggles that make up a marriage in the song “The Little Things You Do Together.” 1984’s Sunday in the Park With George, which is, on some level, a two-and-a-half hour recitation of these kinds of lists, reveals what was hidden all along: The creative process itself is nothing if not a series of little things collaborators do together that add up to something that has the power and weight of a marriage, or a magic potion, or a landmark painting, or history itself.

Like Shakespeare’s, Sondheim’s work is filled with surface delights, but rewards deeper and deeper engagement. Even in his weaker work, there’s always a new layer to be found, whether it’s some lyrical grace note or the way a musical theme threads throughout a show. Assassins is a musical I’ve never much cared for, but listening this morning to “Another National Anthem,” I was struck by its prophetic power. It saw how white resentment and feeling of grievance would blossom into entitlement and violence, and the way it told us that “there are those who like extremes/ there are those who thrive on chaos/ and despair.” Shakespeare pushed his characters toward a deeper engagement with the human condition, bringing a new psychological depth to the Elizabethan stage; Sondheim did the same, rooting the book musical ever deeper in character with each show. And like Shakespeare, Sondheim was obsessed with the dialectic, with setting two opposing ideas or emotional states against one another and letting them duke it out. The word he used to describe this was “ambivalence,” which he called his “favorite thing to write about … because it’s the way I feel and I think it’s the way that most people feel and it wasn’t dealt with very much on the musical stage.”  This ambivalence also allowed him to infuse his musicals with a powerful and profound level of subtext and irony, writing songs where characters don’t always mean what they say, or where the music takes on a completely different emotional texture from the words in order to expose a character’s inner conflicts.

At times in his career, Sondheim’s essaying of ambivalence would bring on the accusation that he was too intellectual, or too cold. But ambivalence is actually a state of deep feeling. Perhaps no song demonstrates this better than “Send in the Clowns,” from A Little Night Music. The song is sung by Desiree, an aging actress. Frederik, the man she has loved for decades, has just confessed he loves her, but will not leave his wife. Originally, Sondheim had felt that Frederik should have a song in the scene, particularly as Desiree, played by the dramatic actress Glynis Johns, wasn’t meant to be a singing part; director Hal Prince convinced him otherwise. Since Johns was already cast, and not a trained musical theater performer, the song would have to be written to her particular strengths and weaknesses. It was a puzzle Sondheim solved by using short lyrical phrases that ended in consonants, so that notes would not have to be held for long, and keeping the melodic phrases simple within a fairly narrow range. The results give the song a restraint that makes its bitterness all the more powerful, as its opening lines (Isn’t it rich?/ Are we a pair?) slowly give way to a darkly comic grief (Don’t you love farce?/ My fault, I fear/ I thought that you’d want what I want/ Sorry my dear). The power of the song comes from this restraint, from Sondheim’s use of irony and subtext. It is anything but cold. It’s a puzzle, yes, but one infused with transcendence.

Bounce, Sondheim’s last completed new musical, opened to negative reviews in 2003.* A revised version, now titled Road Show, did not fare much better when it opened off-Broadway in 2008. For the most part, the 21^st century is dotted with incomplete projects and rewrites of older show like The Frogs. For the last several years, he had been working with the playwright David Ives on an adaptation of two Buñuel films, tentatively titled Square One, but even though he recently announced on The Late Show With Stephen Colbert that he hoped to see it premiere next year, I never truly believed it would happen; it had simply been so long since a new work that I had given up hope that we would ever get a new Sondheim musical.* His death Friday at the age of 91 was hardly unexpected—what 91 year old’s death is?—but I find myself devastated nonetheless. His achievement was so vast, so epoch-defining, that we cannot help but grieve the man who gave us so much.

Sondheim’s impact upon this century is felt in his generous citizenship in the theater community. He regularly attended shows—in his final interview, conducted less than a week before his death, he talks about looking forward to seeing Dana H. and Is This a Room, two experimental documentary theater productions running in rep on Broadway.* He remained open-minded about directorial takes on his work, greenlighting a production of Sweeney Todd set in an insane asylum where the cast all played their own instruments and an immersive production in which the audience ate real meat pies, and the new Broadway revival of Company has been rewritten to flip the gender of its protagonist. And Sondheim served as a mentor to generations of musical theater writers, including Lin-Manuel Miranda, even though Miranda’s artistic mission of reconciling the Broadway musical with the popular musical form of hip hop is in many ways a reversal of Sondheim’s own infusion of the popular musical with the complexity of classical music.

This is one reason we mourn him, of course. But another is because, like Shakespeare, his work follows us through each stage of our own lives, adding complexity and illuminating depths we struggle to articulate. From Into the Woods, which takes the materials of childhood and spins them into a profound morality tale about selfishness, community, and storytelling, to Follies, which examines aging and regret, Sondheim has given us profound, moving, complex, brilliant looks at innumerable moods: desire, revenge, the creative process, history, rage, love, politics, marriage, parenthood, grief, and joy chief among them. To enter a Sondheim musical is to have both your artistic horizons and your humanity expanded just a little bit. It is to hear language anew, and reconsider how words and music can create meaning between them that neither was capable of on its own. It is to know that no one is alone, and to yearn for someone to hold me too close. It is to look at the unsolvable puzzle of life, and find endless riches within it.