A Starter Kit for Getting Into Stephen Sondheim, the Legend of Musical Theater

This past Friday, the composer and lyricist, Stephen Sondheim, a god in musical theater, died. Though many fans knew his death was coming at some point—he was, after all, 91—the news still felt like a gut punch. Many of us assumed that Sondheim would always be with us. Just in September, he told Stephen Colbert that he was writing a new musical, and his past works are a vital part of the cultural conversation this fall. Revivals of his shows Assassins, a fantasy that brings successful and would-be presidential killers together in a carnival, and Company, about a single person's anxiety, are playing off and on Broadway. West Side Story, for which he wrote the lyrics, is once again a major motion picture, this one directed by Steven Spielberg and coming out December 10.

If you have a musical theater fan in your life, chances are you were privy to some of the mourning that started immediately after the announcement of Sondheim's passing. And whether you're a neophyte who wants to get into his work, a casual fan looking to go deeper, or an obsessive reading everything you possibly can about his incredible career, here's a starter kit for you to dig into the work of perhaps the greatest of all time.

Sondheim was just 27 when West Side Story debuted on Broadway. Arguably the most famous work he was ever associated with, Sondheim nevertheless has a complicated relationship with the musical. He wrote in his book Finishing the Hat that he always liked writing music more than lyrics, and being Leonard Bernstein's lyricist on West Side Story branded him in the public eye in a way that initially limited public perception of his work.

Bernstein wanted the words to the songs to be "poetic" in a way that annoyed Sondheim. He didn't think these street kid characters would be singing about a "morning star." Of course, that poeticism is beautiful in its own occasionally corny way, but Sondheim got more of the specificity he was looking for into "Something's Coming," Tony's first act "I want" song. It was a number written well into rehearsal. Sondheim threaded a baseball metaphor, something Tony would know well about, into his prayer/premonition for a miracle. "Something's coming, don't know when, but it's soon. Catch the moon. One-handed catch!"

Company was the fourth show of Sondheim's that went to Broadway featuring both his music and lyrics with a book by George Furth. And while A Funny Thing Happened on the Way to the Forum is hilarious, and Anyone Can Whistle and Do I Hear a Waltz? are both fascinating and flawed artifacts despite being flops, Company is the project that makes Sondheim's true power as an artist clear. First of all, Company's subject matter was not something Broadway was used to in 1970. It wasn't a period piece or a fantasy or a tragedy. It was just a story about a guy in the present day, trying to figure out his life. Now its closing song, "Being Alive," is maybe best known as the song Adam Driver sings at the end of Marriage Story, but it's also one of Sondheim's most powerful compositions. For me, the crucial trick of "Being Alive" is the mid-song grammatical change. Bobby begins passively: "Someone to hold you too close, someone to hurt you too deep." By the end, he realizes he's asking. "Somebody hold me too close," he demands. "Somebody hurt me too deep."

Sondheim's biggest pop hit, "Send in the Clowns," comes from A Little Night Music, and he confides in his book he has no idea why it was recorded so much. But arguably the most extraordinary song from the show, an adaptation of Ingmar Bergman's Smiles of a Summer Night written with Hugh Wheeler, is "The Miller's Son." In the second act, the maid Petra has sex with the manservant Frid. As he sleeps, she considers the men she could possibly marry, and how she's going to enjoy herself "in the meanwhile." It's a song that builds and swells, and features some of Sondheim's most tantalizing wordplay. Petra succinctly sums up how quickly time passes: "It's a very short road from the pinch and the punch to the paunch and the pouch and the pension." The alliteration is fantastic, but it's also what's conveyed within that brutally describes the way life demolishes a person.

Take it from Sondheim himself: If he had to name a favorite of his songs, he would say this one, he explained in Finishing the Hat. "What I love is its ambition, its attempt to collapse past, present and future into one packaged song form," he wrote. In conjunction with John Weidman, Pacific Overtures was an ambitious project, a musical about the westernization of Japan in the 19th century told from the perspective of the Japanese, using Kabuki styles. And "Someone in a Tree" is a complicated song. It chronicles a key part of the plot—the American Commodore Perry meeting with the samurai Kayama—but no one knows what was said in the "treaty house." So an Old Man remembers what he saw in his youth while climbing a tree. But that account is disputed all throughout the song, proving the fallibility of history.

Sondheim's work has been praised for its profundity, but it's also worth remembering that he loved to have fun with his characters and their words. There is no better example of this than "A Little Priest" from Sweeney Todd, another collaboration with Hugh Wheeler. Sweeney Todd itself is just a remarkable thing. Sondheim brought horror to musical theater, creating something truly scary with his interpretation of this tale of the "demon barber of fleet street" who slits throats on his path to revenge while his accomplice, Mrs. Lovett, bakes the victims into meat pies. Through the rhythms of the piano, Sondheim was able to convey genuine fright, but the moment that Sweeney and Mrs. Lovett decide what they are going to do with their dead is downright hilarious. In this duet, they find every way possible to pun about eating human flesh.

"Art isn't easy." That's not a lyric from "Move On," the song I have decided to put in here, but it's the quickest summation of Sondheim and James Lapine's Sunday in the Park with George, a time-traveling musical, which starts with Georges Seurat painting "A Sunday on La Grande Jatte" and then leaps forward in time to his potential descendant making light installations called "Chromolumes." If "art isn't easy," making art about art is even harder, and yet Sunday in the Park with George manages to accomplish that, weaving a narrative about time and capitalism and beauty. In the final moments the present and the past converge, with the two Georges becoming one, and his muse, Dot, emerging to tell him to persist. "Stop worrying if your vision is new. Let others make that decision, they usually do," she sings, perhaps the most eloquent response to critics ever.

I could have picked any number of songs from Into the Woods, Sondheim and Lapine's mashup of fairytale stories into a parable about wishes and their consequences. This, however, is a personal favorite. The Baker's Wife has just slept with Cinderella's Prince, and she considers her options. Should she pursue a royal romance? Or go back to her husband? "Must it all be either less or more, either plain or grand? Is it always 'or'? Is it never 'and'?" Rarely have the essential questions of the world been made so clear and yet presented with all the grey areas.

Sondheim was a huge movie buff, and since his death, a list of his favorite films has been circulating. While some of his shows have been adapted for the screen with varying degrees of success, he won his Oscar for something completely out of left field. Warren Beatty asked him to write the music for his comic book detective story Dick Tracy, and Sondheim came up with this seductive number for the moll portrayed by Madonna.

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