Stephen Sondheim

Hammerstein about 1940

When Sondheim was about ten years old (around the time of his parents' divorce), he became friends with James Hammerstein, son of lyricist and playwright Oscar Hammerstein II. The elder Hammerstein became Sondheim's surrogate father, influencing him profoundly and developing his love of musical theatre. Sondheim met Hal Prince, who would direct many of his shows, at the opening of South Pacific, Hammerstein's musical with Richard Rodgers. The comic musical he wrote at George School, By George, was a success among his peers and buoyed the young songwriter's self-esteem. When Sondheim asked Hammerstein to evaluate it as though he had no knowledge of its author, he said it was the worst thing he had ever seen: "But if you want to know why it's terrible, I'll tell you." They spent the rest of the day going over the musical, and Sondheim later said, "In that afternoon I learned more about songwriting and the musical theater than most people learn in a lifetime."[17]

Hammerstein designed a course of sorts for Sondheim on constructing a musical. He had the young composer write four musicals, each with one of the following conditions:

• Based on a play he admired; Sondheim chose George S. Kaufman and Marc Connelly's Beggar on Horseback (which became All That Glitters)
• Based on a play he liked but thought flawed; Sondheim chose Maxwell Anderson's High Tor
• Based on an existing novel or short story not previously dramatized, which became his unfinished version of Mary Poppins (titled Bad Tuesday),[18] unrelated to the musical film and stage play scored by the Sherman Brothers)
• An original, which became Climb High

None of the "assignment" musicals were produced professionally. High Tor and Mary Poppins have never been produced: The rights holder for the original High Tor refused permission, and Mary Poppins was unfinished.[19]

Sondheim began attending Williams College, a liberal arts college in Williamstown, Massachusetts whose theatre program attracted him.[20] His first teacher there was Robert Barrow:

 ... everybody hated him because he was very dry, and I thought he was wonderful because he was very dry. And Barrow made me realize that all my romantic views of art were nonsense. I had always thought an angel came down and sat on your shoulder and whispered in your ear 'dah-dah-dah-DUM.' Never occurred to me that art was something worked out. And suddenly it was skies opening up. As soon as you find out what a leading tone is, you think, Oh my God. What a diatonic scale is – Oh my God! The logic of it. And, of course, what that meant to me was: Well, I can do that. Because you just don't know. You think it's a talent, you think you're born with this thing. What I've found out and what I believed is that everybody is talented. It's just that some people get it developed and some don't.[21]

The composer told Meryle Secrest, "I just wanted to study composition, theory, and harmony without the attendant musicology that comes in graduate school. But I knew I wanted to write for the theatre, so I wanted someone who did not disdain theatre music."[22] Barrow suggested that Sondheim study with Milton Babbitt, whom Sondheim described as "a frustrated show composer" with whom he formed "a perfect combination".[22] When he met Babbitt, he was working on a musical for Mary Martin based on the myth of Helen of Troy. Sondheim and Babbitt would meet once a week in New York City for four hours (at the time, Babbitt was teaching at Princeton University). According to Sondheim, they spent the first hour dissecting Rodgers and Hart or George Gershwin or studying Babbitt's favorites (Buddy DeSylva, Lew Brown and Ray Henderson). They then proceeded to other forms of music (such as Mozart's Jupiter Symphony), critiquing them the same way.[23] Babbitt and Sondheim, fascinated by mathematics, studied songs by a variety of composers (especially Jerome Kern). Sondheim told Secrest that Kern had the ability "to develop a single motif through tiny variations into a long and never boring line and his maximum development of the minimum of material". He said about Babbitt, "I am his maverick, his one student who went into the popular arts with all his serious artillery".[22] At Williams, Sondheim wrote a musical adaption of Beggar on Horseback (a 1924 play by George S. Kaufman and Marc Connelly, with permission from Kaufman) which had three performances.[24] A member of the Beta Theta Pi fraternity, he graduated magna cum laude in 1950.

"A few painful years of struggle" followed, when Sondheim auditioned songs, lived in his father's dining room to save money and spent time in Hollywood writing for the television series Topper.[10] He devoured 1940s and 1950s films, and has called cinema his "basic language";[11] his film knowledge got him through The $64,000 Question contestant tryouts. Sondheim dislikes movie musicals, favoring classic dramas such as Citizen Kane, The Grapes of Wrath and A Matter of Life and Death: "Studio directors like Michael Curtiz and Raoul Walsh ... were heroes of mine. They went from movie to movie to movie, and every third movie was good and every fifth movie was great. There wasn't any cultural pressure to make art".[25]

At age 22, Sondheim had finished the four shows requested by Hammerstein. Julius and Philip Epstein's Front Porch in Flatbush, unproduced at the time, was being shopped around by Lemuel (Lem) Ayers. Ayers approached Frank Loesser and another composer, who turned him down. Ayers and Sondheim met as ushers at a wedding, and Ayers commissioned Sondheim for three songs for the show; Julius Epstein flew in from California and hired Sondheim, who worked with him in California for four or five months. After eight auditions for backers, half the money needed was raised. The show, retitled Saturday Night, was intended to open during the 1954–55 Broadway season; however, Ayers died of leukemia in his early forties. The rights transferred to his widow, Shirley, and due to her inexperience the show did not continue as planned;[3] it opened off-Broadway in 2000. Sondheim later said, "I don't have any emotional reaction to Saturday Night at all – except fondness. It's not bad stuff for a 23-year-old. There are some things that embarrass me so much in the lyrics – the missed accents, the obvious jokes. But I decided, leave it. It's my baby pictures. You don't touch up a baby picture – you're a baby!"[11]

Burt Shevelove invited Sondheim to a party; Sondheim arrived before him, and knew no one else well. He saw a familiar face: Arthur Laurents, who had seen one of the auditions of Saturday Night, and they began talking. Laurents told him he was working on a musical version of Romeo and Juliet with Leonard Bernstein, but they needed a lyricist; Betty Comden and Adolph Green, who were supposed to write the lyrics, were under contract in Hollywood. He said that although he was not a big fan of Sondheim's music, he enjoyed the lyrics from Saturday Night and he could audition for Bernstein. The following day, Sondheim met and played for Bernstein, who said he would let him know. The composer wanted to write music and lyrics; after consulting with Hammerstein, Bernstein told Sondheim he could write music later.[3] In 1957, West Side Story opened; directed by Jerome Robbins, it ran for 732 performances. Sondheim has expressed dissatisfaction with his lyrics, saying that they do not always fit the characters and are sometimes too consciously poetic. Initially Bernstein was also credited as a co-writer of the lyrics; later, however, Bernstein offered Sondheim solo credit, as Sondheim had essentially done all of them. And, in fact, The New York Times review of the show never even mentioned the lyrics.[26] Sondheim described the division of the royalties, saying that Bernstein received three percent and he received one percent. Bernstein suggested evening the percentage at two percent each, but Sondheim refused because he was satisfied just getting the credit. Sondheim later said he wished "someone stuffed a handkerchief in my mouth because it would have been nice to get that extra percentage".[3]

After West Side Story opened, Shevelove lamented the lack of "low-brow comedy" on Broadway and mentioned a possible musical based on Plautus' Roman comedies. When Sondheim was interested in the idea he called a friend, Larry Gelbart, to co-write the script. The show went through a number of drafts, and was interrupted briefly by Sondheim's next project.[27]

In 1959, Sondheim was approached by Laurents and Robbins for a musical version of Gypsy Rose Lee's memoir after Irving Berlin and Cole Porter turned it down. Sondheim agreed, but Ethel Merman – cast as Mama Rose – had just finished Happy Hunting with an unknown composer (Harold Karr) and lyricist (Matt Dubey). Although Sondheim wanted to write the music and lyrics, Merman refused to let another first-time composer write for her and demanded that Jule Styne write the music.[28] Sondheim, concerned that writing lyrics again would pigeonhole him as a lyricist, called his mentor for advice. Hammerstein told him he should take the job, because writing a vehicle for a star would be a good learning experience. Sondheim agreed; Gypsy opened on May 21, 1959, and ran for 702 performances.[3]

In 1960, Sondheim lost his mentor and father figure, Oscar Hammerstein.[29] He remembered that shortly before Hammerstein's death, Hammerstein had given him a portrait of himself. Sondheim asked him to inscribe it, and said later about the request that it was "weird ... it's like asking your father to inscribe something". Reading the inscription ("For Stevie, My Friend and Teacher") choked up the composer, who said: "That describes Oscar better than anything I could say."[30]

When he walked away from the house that evening, Sondheim remembered a sad, sinking feeling that they had said their final goodbye. He never saw his mentor again; three days later, Hammerstein died of stomach cancer and Hammerstein's protégé eulogized him at his funeral.

Sondheim had participated in three straight hits, but his next show – 1964's Anyone Can Whistle – was a nine-performance bomb (although it introduced Angela Lansbury to musical theatre). Do I Hear a Waltz?, based on Arthur Laurents' 1952 play The Time of the Cuckoo, was intended as another Rodgers and Hammerstein musical with Mary Martin in the lead. A new lyricist was needed,[31] and Laurents and Rodgers' daughter, Mary, asked Sondheim to fill in. Although Richard Rodgers and Sondheim agreed that the original play did not lend itself to musicalization, they began writing the musical version.[32] The project had many problems, Rodgers' alcoholism among them; Sondheim, calling it the one project he regretted, then decided to work only when he could write both music and lyrics.[11] He asked author and playwright James Goldman to join him as bookwriter for a new musical. Inspired by a New York Times article about a gathering of former Ziegfeld Follies showgirls, it was entitled The Girl Upstairs (and would later become Follies).[33]

In 1966, Sondheim semi-anonymously provided lyrics for "The Boy From...", a parody of "The Girl from Ipanema" in the off-Broadway revue The Mad Show. The song was credited to "Esteban Ria Nido",[34] Spanish for "Stephen River Nest", and in the show's playbill the lyrics were credited to "Nom De Plume". That year Goldman and Sondheim hit a creative wall on The Girls Upstairs, and Goldman asked Sondheim about writing a TV musical. The result was Evening Primrose, with Anthony Perkins and Charmian Carr. Written for the anthology series ABC Stage 67 and produced by Hubbell Robinson, it was broadcast on November 16, 1966. According to Sondheim and director Paul Bogart, the musical was written only because Goldman needed money for rent. The network disliked the title and Sondheim's alternative, A Little Night Music.[35]

After Sondheim finished Evening Primrose, Jerome Robbins asked him to adapt Bertolt Brecht's The Measures Taken despite the composer's general dislike of Brecht's work. Robbins wanted to adapt another Brecht play, The Exception and the Rule, and asked John Guare to adapt the book. Leonard Bernstein had not written for the stage in some time, and his contract as conductor of the New York Philharmonic was ending. Sondheim was invited to Robbins' house in the hope that Guare would convince him to write the lyrics for a musical version of The Exception and the Rule; according to Robbins, Bernstein would not work without Sondheim. When Sondheim agreed, Guare asked: "Why haven't you all worked together since West Side Story?" Sondheim answered, "You'll see". Guare said that working with Sondheim was like being with an old college roommate, and he depended on him to "decode and decipher their crazy way of working"; Bernstein worked only after midnight, and Robbins only in the early morning. Bernstein's score, which was supposed to be light, was influenced by his need to make a musical statement.[36] Stuart Ostrow, who worked with Sondheim on The Girls Upstairs, agreed to produce the musical (now entitled A Pray By Blecht and, later, The Race to Urga). An opening night was scheduled, but during auditions Robbins asked to be excused for a moment. When he did not return, a doorman said he had gotten into a limousine to go to John F. Kennedy International Airport. Bernstein burst into tears and said, "It's over"; Sondheim said, "I was ashamed of the whole project. It was arch and didactic in the worst way."[37] He wrote one-and-a-half songs and threw them away, the only time he has ever done that. Eighteen years later, Sondheim refused Bernstein and Robbins' request to retry the show.[36]

Stephen Sondheim House, Turtle Bay, New York City, New York

He has lived in a Turtle Bay, Manhattan brownstone since writing Gypsy in 1959. Ten years later, while he was playing music he heard a knock on the door. His neighbor, Katharine Hepburn, was in "bare feet – this angry, red-faced lady" and told him "You have been keeping me awake all night!" (she was practicing for her musical debut in Coco). When Sondheim asked why she had not asked him to play for her, she said she lost his phone number. According to Sondheim, "My guess is that she wanted to stand there in her bare feet, suffering for her art".[38]

After Do I Hear a Waltz?, Sondheim devoted himself solely to writing both music and lyrics for the theater - and in 1970, he began a collaboration with director Harold Prince that would result in a body of work that is considered one of the high water marks of musical theater history.

Their first show with Prince as director was the 1970 concept musical Company. A show about a single man and his married friends, Company (with a book by George Furth) lacked a straightforward plot, and was instead centered around themes such as marriage and the difficulty of making an emotional connection with another person. It opened on April 26, 1970 at the Alvin Theatre, where it ran for 705 performances after seven previews, and won Tony Awards for best musical, best music and best lyrics. It was revived on Broadway in 1995 and 2006, and will be revived again in 2020 (in a version where the main character is gender-swapped).

Follies (1971), with a book by James Goldman, opened on April 4, 1971 at the Winter Garden Theatre and ran for 522 performances after 12 previews. The plot centers on a reunion, in a crumbling Broadway theatre scheduled for demolition, of performers in Weismann's Follies (a musical revue, based on the Ziegfeld Follies, which played in that theatre between the world wars). The production, one of the most lavish of its time, also featured choreography and co-direction by Michael Bennett, who went on to create A Chorus Line (1975). The show enjoyed two revivals on Broadway in 2001 and 2011.

A Little Night Music (1973), with a more traditional plot based on Ingmar Bergman's Smiles of a Summer Night and a score primarily in waltz time, was one of the composer's greatest commercial successes. Time magazine called it "Sondheim's most brilliant accomplishment to date".[39] "Send in the Clowns", a song from the musical, was a hit for Judy Collins, and became Sondheim's most well-known song. The show opened on Broadway at the Shubert Theatre on February 25, 1973, and ran for 601 performances and 12 previews. It was revived on Broadway in 2009.

Pacific Overtures (1976), with a book by John Weidman, was the most non-traditional of the Sondheim-Prince collaborations: the show explored the westernization of Japan, and was originally presented in Kabuki style. The show closed after a run of 193 performances, and was revived on Broadway in 2004.

Sweeney Todd: The Demon Barber of Fleet Street (1979), Sondheim's most operatic score and libretto (which, with Pacific Overtures and A Little Night Music, has been produced in opera houses), explores an unlikely topic: murderous revenge and cannibalism. The book, by Hugh Wheeler, is based on Christopher Bond's 1973 stage version of the Victorian original.[40][41][42][43][44] The show has since been revived on Broadway twice (1989, 2005), and has been performed in musical theaters and opera houses alike. It ran off-Broadway at the Barrow Street Theatre until August 26, 2018.

Merrily We Roll Along (1981), with a book by George Furth, is one of Sondheim's more traditional scores; Frank Sinatra and Carly Simon have recorded songs from the musical. According to Sondheim's music director, Paul Gemignani, "Part of Steve's ability is this extraordinary versatility." However, the show was not the success their previous collaborations had been: after a chaotic series of preview performances, the show opened to widely negative reviews, and closed after a run of less than two weeks. Due to the high quality of Sondheim's score, however, the show has been repeatedly revised and produced in the ensuing years. Martin Gottfried wrote, "Sondheim had set out to write traditional songs ... But [despite] that there is nothing ordinary about the music."[45] Sondheim later said: "Did I feel betrayed? I'm not sure I would put it like that. What did surprise me was the feeling around the Broadway community – if you can call it that, though I guess I will for lack of a better word – that they wanted Hal and me to fail."[38]

Merrily's failure greatly affected Sondheim; he was ready to quit theatre and do movies, create video games or write mysteries: "I wanted to find something to satisfy myself that does not involve Broadway and dealing with all those people who hate me and hate Hal."[46] Sondheim and Prince's collaboration was suspended from Merrily to the 2003 production of Bounce, another failure.

However, Sondheim decided "that there are better places to start a show" and found a new collaborator in James Lapine after he saw Lapine's Twelve Dreams off-Broadway in 1981: "I was discouraged, and I don't know what would have happened if I hadn't discovered Twelve Dreams at the Public Theatre";[38] Lapine has a taste "for the avant-garde and for visually-oriented theatre in particular". Their first collaboration was Sunday in the Park with George (1984), with Sondheim's music evoking Georges Seurat's pointillism. Sondheim and Lapine won the 1985 Pulitzer Prize for Drama for the play, and it was revived on Broadway in 2008, and again in a limited run in 2017.

They collaborated on Into the Woods (1987), a musical based on several Brothers Grimm fairy tales. Although Sondheim has been called the first composer to bring rap music to Broadway (with the Witch in the opening number of "Into the Woods"), he attributes the first rap in theatre to Meredith Willson's "Rock Island" from The Music Man.[23] The show was revived on Broadway in 2002.

Sondheim and Lapine's last work together was the rhapsodic Passion (1994), adapted from Ettore Scola's Italian film Passione D'Amore. With a run of 280 performances, Passion was the shortest-running show to win a Tony Award for Best Musical.[47]

Assassins opened off-Broadway at Playwrights Horizons on December 18, 1990, with a book by John Weidman. The show explored, in revue form, a group of historical figures who tried (either with success or without) to assassinate the President of the United States. The musical closed on February 16, 1991, after 73 performances. The show eventually received a Broadway production in 2004.

Saturday Night was shelved until its 1997 production at London's Bridewell Theatre. The following year, its score was recorded; a revised version, with two new songs, ran off-Broadway at Second Stage Theatre in 2000 and at London's Jermyn Street Theatre in 2009.[48]

During the late 1990s, Sondheim and Weidman reunited for Wise Guys, a musical comedy following brothers Addison and Wilson Mizner. A Broadway production, starring Nathan Lane and Victor Garber, directed by Sam Mendes and planned for the spring of 2000,[49] was delayed. Renamed Bounce in 2003, it was produced at the Goodman Theatre in Chicago and the Kennedy Center in Washington, D.C., in a production directed by Harold Prince, his first collaboration with Sondheim since 1981. Although after poor reviews Bounce never reached Broadway, a revised version opened off-Broadway as Road Show at the Public Theater on October 28, 2008. Directed by John Doyle, it closed on December 28, 2008.

Asked about writing new work, Sondheim replied in 2006: "No ... It's age. It's a diminution of energy and the worry that there are no new ideas. It's also an increasing lack of confidence. I'm not the only one. I've checked with other people. People expect more of you and you're aware of it and you shouldn't be."[50] In December 2007 he said that in addition to continuing work on Bounce, he was "nibbling at a couple of things with John Weidman and James Lapine".[51]

Lapine created a multimedia production, originally entitled Sondheim: a Musical Revue, which was scheduled to open in April 2009 at the Alliance Theatre in Atlanta; however, it was canceled due to "difficulties encountered by the commercial producers attached to the project ... in raising the necessary funds".[52][53] A revised version, Sondheim on Sondheim, was produced at Studio 54 by the Roundabout Theatre Company; previews began on March 19, 2010, and it ran from April 22 to June 13. The revue's cast included Barbara Cook, Vanessa L. Williams, Tom Wopat, Norm Lewis and Leslie Kritzer.[54]

Sondheim collaborated with Wynton Marsalis on A Bed and a Chair: A New York Love Affair, an Encores! concert on November 13–17, 2013 at New York City Center. Directed by John Doyle with choreography by Parker Esse, it consisted of "more than two dozen Sondheim compositions, each piece newly re-imagined by Marsalis".[55] The concert featured Bernadette Peters, Jeremy Jordan, Norm Lewis, Cyrille Aimée, four dancers and the Jazz at Lincoln Center Orchestra conducted by David Loud.[56] In Playbill, Steven Suskin described the concert as "neither a new musical, a revival, nor a standard songbook revue; it is, rather, a staged-and-sung chamber jazz rendition of a string of songs ... Half of the songs come from Company and Follies; most of the other Sondheim musicals are represented, including the lesser-known Passion and Road Show".[57]

For the 2014 film adaptation of Into the Woods, Sondheim wrote a new song, "She'll Be Back", which was to be sung by The Witch, but was eventually cut.

In February 2012 it was announced that Sondheim would collaborate on a new musical with David Ives, and he had "about 20–30 minutes of the musical completed".[58][59][60][61][62] The show, tentatively called All Together Now, was assumed to follow the format of Merrily We Roll Along. Sondheim described the project as "two people and what goes into their relationship ... We'll write for a couple of months, then have a workshop. It seemed experimental and fresh 20 years ago. I have a feeling it may not be experimental and fresh any more".[63] On October 11, 2014, it was confirmed the Sondheim and Ives musical would be based on two Luis Buñuel films (The Exterminating Angel and The Discreet Charm of the Bourgeoisie) and would reportedly open (in previews) at the Public Theater in 2017.[64]

In August 2016, a reading for the musical was held at the Public Theater, and it was reported that only the first act was finished, which cast doubt on the speculated 2017 start of previews.[65] There was a workshop in November 2016, with the participation of Matthew Morrison, Shuler Hensley, Heidi Blickenstaff, Sierra Boggess, Gabriel Ebert, Sara Stiles, Michael Cerveris and Jennifer Simard.[66] The working title was reported to be Buñuel by the New York Post and other outlets, but Sondheim later clarified that this was an error and that they still had no title.[67] As of April 2019, a date for a musical titled Buñuel (by Sondheim and David Ives; directed by Joe Mantello) has been announced on the New York City Theatre website, beginning August 24, 2019. However, in June 2019, the Public Theatre announced that it would not be part of its 2019-2020 season, as it was still in development, but will be produced "when it is ready".[68]

The Kennedy Center held a Sondheim Celebration, running from May to August 2002, consisting of six of Sondheim's musicals: Sweeney Todd, Company, Sunday in the Park With George, Merrily We Roll Along, Passion and A Little Night Music.[69][70][71] On April 28, 2002, in connection with the Sondheim Celebration Sondheim and Frank Rich of the New York Times had a conversation.[69][72] They appeared in four interviews, entitled "A Little Night Conversation with Stephen Sondheim",[73][74] in California[75][76][77] and Portland, Oregon in March 2008[78] and at Oberlin College in September. The Cleveland Jewish News reported on their Oberlin appearance: "Sondheim said: 'Movies are photographs; the stage is larger than life.' What musicals does Sondheim admire the most? Porgy and Bess tops a list which includes Carousel, She Loves Me, and The Wiz, which he saw six times. Sondheim took a dim view of today's musicals. What works now, he said, are musicals that are easy to take; audiences don't want to be challenged".[79][80] Sondheim and Rich had additional conversations on January 18, 2009 at Avery Fisher Hall,[81] on February 2 at the Landmark Theatre in Richmond, Virginia,[82] on February 21 at the Kimmel Center in Philadelphia[83] and on April 20 at the University of Akron in Akron, Ohio.[84] The conversations were reprised at Tufts and Brown University in February 2010, at the University of Tulsa in April[85] and at Lafayette College on March 8, 2011.[86] Sondheim had another "conversation with" Sean Patrick Flahaven (associate editor of The Sondheim Review) at the Kravis Center in West Palm Beach on February 4, 2009, in which he discussed many of his songs and shows: "On the perennial struggles of Broadway: 'I don't see any solution for Broadway's problems except subsidized theatre, as in most civilized countries of the world.'"[87]

On February 1, 2011, Sondheim joined former Salt Lake Tribune theatre critic Nancy Melich before an audience of 1,200 at Kingsbury Hall. Melich described the evening:

He was visibly taken by the university choir, who sang two songs during the evening, "Children Will Listen" and "Sunday", and then returned to reprise "Sunday". During that final moment, Sondheim and I were standing, facing the choir of students from the University of Utah's opera program, our backs to the audience, and I could see tears welling in his eyes as the voices rang out. Then, all of a sudden, he raised his arms and began conducting, urging the student singers to go full out, which they did, the crescendo building, their eyes locked with his, until the final "on an ordinary Sunday" was sung. It was thrilling, and a perfect conclusion to a remarkable evening – nothing ordinary about it.[88]

On March 13, 2008, A Salon With Stephen Sondheim (which sold out in three minutes) was hosted by the Academy for New Musical Theatre in Hollywood.[89][90]

An avid fan of games, in 1968 and 1969 Sondheim published a series of cryptic crossword puzzles in New York magazine. In 1987 Time called his love of puzzlemaking "legendary in theater circles", adding that the central character of Anthony Shaffer's play Sleuth was inspired by the composer. According to a rumor (denied by Shaffer in a March 10, 1996 New York Times interview), Sleuth had the working title Who's Afraid of Stephen Sondheim?[10] His love of puzzles and mysteries is evident in The Last of Sheila, an intricate whodunit written with longtime friend Anthony Perkins. The 1973 film, directed by Herbert Ross, featured Dyan Cannon, Raquel Welch, James Mason, James Coburn and Richard Benjamin.

Sondheim tried playwriting one more time, collaborating with Company librettist George Furth on Getting Away with Murder in 1996, but the unsuccessful Broadway production closed after 29 previews and 17 performances. His compositions have included a number of film scores, including a set of songs written for Warren Beatty's 1990 film version of Dick Tracy. One of Sondheim's songs for the film, "Sooner or Later (I Always Get My Man)", sung in the movie by Madonna, won him an Academy Award.

According to Sondheim, he was asked to translate Mahagonny-Songspiel: "But, I'm not a Brecht/Weill fan and that's really all there is to it. I'm an apostate: I like Weill's music when he came to America better than I do his stuff before ... I love The Threepenny Opera but, outside of The Threepenny Opera, the music of his I like is the stuff he wrote in America – when he was not writing with Brecht, when he was writing for Broadway."[91] He turned down an offer to musicalize Nathanael West's A Cool Million with James Lapine around 1982.[92][93]

Sondheim worked with William Goldman on Singing Out Loud, a musical film, in 1992, penning the song "Water Under the Bridge".[94][95] According to the composer, Goldman wrote one or two drafts of the script and Sondheim wrote six-and-a-half songs when director Rob Reiner lost interest in the project. "Dawn" and "Sand", from the film, were recorded for the albums Sondheim at the Movies and Unsung Sondheim.[91] Sondheim and Leonard Bernstein wrote The Race to Urga, scheduled for Lincoln Center in 1969, but when Jerome Robbins left the project it was not produced.[96]

In 1991 Sondheim worked with Terrence McNally on a musical, All Together Now. McNally said, "Steve was interested in telling the story of a relationship from the present back to the moment when the couple first met. We worked together a while, but we were both involved with so many other projects that this one fell through". The story follows Arden Scott, a 30-something female sculptor, and Daniel Nevin (a slightly-younger, sexually attractive restaurateur). Its script, with concept notes by McNally and Sondheim, is archived in the Harry Ransom Center at the University of Texas at Austin.[97]

In August 2003, Sondheim expressed interest in the idea of a creating a musical adaption of the 1993 comedy film Groundhog Day.[98] However, in a 2008 live chat, he said that "to make a musical of Groundhog Day would be to gild the lily. It cannot be improved."[99] The musical was later created and premiered in 2016 with music and lyrics by Tim Minchin and book by Danny Rubin (screenwriter of the film) with Sondheim's blessing.[100]

Sondheim's 2010 Finishing the Hat annotates his lyrics "from productions dating 1954–1981. In addition to published and unpublished lyrics from West Side Story, Follies and Company, the tome finds Sondheim discussing his relationship with Oscar Hammerstein II and his collaborations with composers, actors and directors throughout his lengthy career".[101][102] The book, first of a two-part series, is named after a song from Sunday in the Park With George. Sondheim said, "It's going to be long. I'm not, by nature, a prose writer, but I'm literate, and I have a couple of people who are vetting it for me, whom I trust, who are excellent prose writers".[103][104] Finishing the Hat was published in October 2010. According to a New York Times review, "The lyrics under consideration here, written during a 27-year period, aren't presented as fixed and sacred paradigms, carefully removed from tissue paper for our reverent inspection. They're living, evolving, flawed organisms, still being shaped and poked and talked to by the man who created them".[105] The book was 11th on the New York Times' Hardcover Nonfiction list for November 5, 2010.[106]

Its sequel, Look, I Made a Hat: Collected Lyrics (1981–2011) with Attendant Comments, Amplifications, Dogmas, Harangues, Digressions, Anecdotes and Miscellany, was published on November 22, 2011. The book, continuing from Sunday in the Park With George (where Finishing the Hat ended), includes sections on Sondheim's work in film and television.[107]

After he was mentored by Oscar Hammerstein II[17] Sondheim has returned the favor, saying that he loves "passing on what Oscar passed on to me".[30] In an interview with Sondheim for The Legacy Project, composer-lyricist Adam Guettel (son of Mary Rodgers and grandson of Richard Rodgers) recalls how as a 14-year-old boy he showed Sondheim his work. Guettel was "crestfallen" since he had come in "sort of all puffed up thinking [he] would be rained with compliments and things", which was not the case since Sondheim had some "very direct things to say". Later, Sondheim wrote and apologized to Guettel for being "not very encouraging" when he was actually trying to be "constructive".[108]

Sondheim also mentored a fledgling Jonathan Larson, attending Larson's workshop for his Superbia (a musical version of Nineteen Eighty-Four). In Larson's musical Tick, Tick... Boom!, the phone message is played in which Sondheim apologizes for leaving early, says he wants to meet him and is impressed with his work. After Larson's death, Sondheim called him one of the few composers "attempting to blend contemporary pop music with theater music, which doesn't work very well; he was on his way to finding a real synthesis. A good deal of pop music has interesting lyrics, but they are not theater lyrics". A musical-theatre composer "must have a sense of what is theatrical, of how you use music to tell a story, as opposed to writing a song. Jonathan understood that instinctively."[109]

Around 2008, Sondheim approached Lin-Manuel Miranda to work with him translating West Side Story lyrics into Spanish for an upcoming Broadway revival.[110][111] Miranda then approached Sondheim with his new project Hamilton, then called The Hamilton Mixtape, which Sondheim gave notes on.[111][112] Sondheim was originally wary of the project saying he was "worried that an evening of rap might get monotonous". However, Sondheim believed Miranda's attention to, and respect for, good rhyming made it work.[112]

A supporter for writers' rights in the theatre industry, Stephen Sondheim is an active member of the Dramatists Guild of America. In 1973, he was elected as the Guild's sixteenth president, and he continued his presidency for the non-profit organization until 1981.