Stephen Sondheim

Oscar Hammerstein c. 1940

When Sondheim was about ten years old (around the time of his parents' divorce), he formed a close friendship with James Hammerstein, son of lyricist and playwright Oscar Hammerstein II, who were neighbors in Bucks County. The elder Hammerstein became Sondheim's surrogate father, influencing him profoundly and developing his love of musical theater. Sondheim met Hal Prince, who would later 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:[18]

• 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),[19] (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 (though a musical version by Arthur Schwartz was produced for television in 1956), and Mary Poppins was unfinished.[20]

In 1960, Sondheim lost his mentor and father figure when Hammerstein died of stomach cancer on August 23, aged 65.[21][22] Sondheim later recalled that 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."[23]

Sondheim began attending Williams College, a liberal arts college in Williamstown, Massachusetts, whose theater program attracted him.[24] 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.' It 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.[25]

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."[26] Barrow suggested that Sondheim study with Milton Babbitt, whom Sondheim described as "a frustrated show composer" with whom he formed "a perfect combination".[26] When they met, Babbitt was working on a musical for Mary Martin based on the myth of Helen of Troy. The two 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.[27] 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".[26] 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.[28] A member of the Beta Theta Pi fraternity,[29] he graduated magna cum laude in 1950.[30]

"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 called cinema his "basic language";[11] his film knowledge got him through The $64,000 Question contestant tryouts. Sondheim disliked 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".[31]

At age 22, Sondheim had finished the four shows requested by Hammerstein. Screenwriters Julius and Philip Epstein's Front Porch in Flatbush, unproduced at the time, was being shopped around by designer and producer Lemuel Ayers. Ayers approached Frank Loesser and another composer who both 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 production 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 where Sondheim arrived before him but 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. Sondheim wanted to write music and lyrics; he consulted with Hammerstein, who said, as Sondheim related in a 2008 New York Times video interview, "Look, you have a chance to work with very gifted professionals on a show that sounds interesting, and you could always write your own music eventually. My advice would be to take the job."[3] West Side Story, directed by Jerome Robbins, opened in 1957 and ran for 732 performances. Sondheim expressed dissatisfaction with his lyrics, saying that they did not always fit the characters and were 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. The New York Times review of the show never even mentioned the lyrics.[32] 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.[33]

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.[34] 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]

The first Broadway production for which Sondheim wrote the music and lyrics was A Funny Thing Happened on the Way to the Forum, which opened in 1962 and ran for 964 performances.[35] The book, based on farces by Plautus, was written by Burt Shevelove and Larry Gelbart. The show won six Tony Awards (including Best Musical)[36] and had the longest Broadway run of any show for which Sondheim wrote both music and lyrics.[37]

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 theater). 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,[38] 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.[39] The project had many difficulties, including Rodgers' alcoholism; 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 Girls Upstairs (and would later become Follies).[40]

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 Río Nido",[41] 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.[42]

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.[43] 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 later said of this experience: "I was ashamed of the whole project. It was arch and didactic in the worst way."[44] He wrote one-and-a-half songs and threw them away, the only time he ever did that. Eighteen years later, Sondheim refused Bernstein and Robbins' request to retry the show.[43]

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

Sondheim lived in a Turtle Bay, Manhattan brownstone from his writing of 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). "I remember asking Hepburn why she didn't just call me, but she claimed not to have my phone number. My guess is that she wanted to stand there in her bare feet, suffering for her art".[45]

Sondheim in New York, 1972

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 resulting in a body of work that is considered one of the high water marks of musical theater history, with critic Howard Kissel writing that the duo had set "Broadway's highest standards".[46][47]

The first Sondheim show with Prince as director was 1970's 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, running for 705 performances after seven previews, and won Tony Awards for Best Musical, Best Music, and Best Lyrics.[48] Company was revived on Broadway in 1995, 2006, and 2021/2022 (the last revival's previews were in November, then was shut down due to the ongoing COVID-19 pandemic; in the last of these, the main character was gender-swapped).[48]

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.[49] The plot centers on a reunion, in a crumbling Broadway theater scheduled for demolition, of performers in Weismann's Follies (a musical revue, based on the Ziegfeld Follies, which played in that theater between the world wars). The production also featured choreography and co-direction by Michael Bennett, who later created A Chorus Line (1975). The show was revived on Broadway in 2001 and 2011.[50][51]

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 among the composer's greatest commercial successes. Time magazine called it "Sondheim's most brilliant accomplishment to date".[52] "Send in the Clowns", a song from the musical, was a hit for Judy Collins and became Sondheim's best-known song. The show opened on Broadway at the Shubert Theatre on February 25, 1973, and ran for 601 performances and 12 previews.[53] It was revived on Broadway in 2009.[54]

Pacific Overtures (1976), with a book by John Weidman, was one of Sondheim's most unconventional efforts: it explored the westernization of Japan, and was originally presented in a mock-Kabuki style.[55] The show closed after a run of 193 performances,[56] and was revived on Broadway in 2004.[57]

Sweeney Todd: The Demon Barber of Fleet Street (1979), with a score by Sondheim and a book by Hugh Wheeler, is based on Christopher Bond's 1973 stage play derived from the Victorian original.[58][59][60][61][62] There will be a Broadway revival at the Lunt-Fontaine Theatre in the spring of 2023, with previews beginning in February, and officially opening in March.

Merrily We Roll Along (1981), with a book by George Furth, is one of Sondheim's more traditional scores; songs from the musical were recorded by Frank Sinatra and Carly Simon. 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."[63] 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."[45] An acclaimed feature documentary on the show and its aftermath, Best Worst Thing That Ever Could Have Happened, directed by Merrily cast member Lonny Price, and produced by Bruce David Klein, Kitt Lavoie, and Ted Schillinger premiered at the New York Film Festival on November 18, 2016. A film adaptation of Merrily We Roll Along, directed by Richard Linklater, began production in 2019 and is expected to continue periodically over the following two decades, to allow the actors to age in real time.[64] There will be an Off-Broadway revival that is scheduled to run between November 2022 and January 2023 at the New York Theatre Workshop.

Merrily's failure greatly affected Sondheim; he was ready to quit theater 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."[65] Following Merrily, Sondheim and Prince did not collaborate again until their 2003 production of Bounce.[66]

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";[45] 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,[67] and it was revived on Broadway in 2008, and again in a limited run in 2017.[68][69]

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 attributed the first rap in theater to Meredith Willson's "Rock Island" from The Music Man (1957).[27] Into the Woods was revived on Broadway in 2002,[70] and at the St. James Theatre in 2022.

Sondheim and Lapine's last collaboration on a musical 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.[71]

In 2013, Lapine directed the HBO feature-length documentary Six by Sondheim, which he executive produced with former New York Times theater critic Frank Rich, an old friend and longtime champion of Sondheim's work.[72] Sondheim himself acts and sings in the documentary as Joe, the cynical theater producer in the song "Opening Doors".[73]

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 Los Angeles Times reported the show "has been sold out since previews began, reflecting the strong appeal of Sondheim's work among the theater crowd."[74] Frank Rich in his review for The New York Times wrote that "Assassins will have to fire with sharper aim and fewer blanks if it is to shoot to kill."[75][76] Assassins eventually had a Broadway run in 2004.[77]

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.[78]

During the late 1990s, Sondheim and Weidman reunited for Wise Guys, a musical comedy based on the lives of colorful businessmen Addison and Wilson Mizner. A Broadway production, starring Nathan Lane and Victor Garber, directed by Sam Mendes and planned for the spring of 2000,[79] 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.[80] 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 December 28, 2008.[81][82][83] The production won the 2009 Obie Award for Music and Lyrics,[84] and the Drama Desk Award for Outstanding Lyrics.[85]

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."[86] 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".[87]

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".[88][89] 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.[90]

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".[91] The concert featured Bernadette Peters, Jeremy Jordan, Norm Lewis, Cyrille Aimée, four dancers and the Jazz at Lincoln Center Orchestra conducted by David Loud.[92] 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".[93]

Stephen Sondheim (2014)

For the 2014 film adaptation of Into the Woods, Sondheim wrote the new song "She'll Be Back", sung by The Witch, which was eventually cut from the film.[94]

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".[95][96][97][98][99] 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".[100] 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.[101] 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.[102] There was a workshop in November 2016, with the participation of Matthew Morrison, Shuler Hensley, Heidi Blickenstaff, Sierra Boggess, Gabriel Ebert, Sarah Stiles, Michael Cerveris, and Jennifer Simard.[103] The working title was reported to be Buñuel by the New York Post and other outlets, but Sondheim later clarified that they still had no title.[104] In June 2019, the Public Theatre denied reports that it would be part of its 2019–2020 season, as it was still in development, but would be produced "when it is ready".[105] On April 27, 2021, it was reported that the musical was no longer in development.[106] While appearing on The Late Show with Stephen Colbert on September 15, 2021, Sondheim announced he was working on a new musical called Square One in collaboration with Ives.[107] The same day, Nathan Lane revealed that he and Bernadette Peters were involved in a reading of this new work.[108] In Sondheim's final interview before his death, he confirmed that Square One was adapted from the Buñuel films.[109]

The Kennedy Center staged a 15-week repertory festival of six Sondheim musicals—Sweeney Todd, Company, Sunday in the Park with George, Merrily We Roll Along, Passion, and A Little Night Music—from May to August 2002.[110][111][112] The Kennedy Center Sondheim Celebration also included Pacific Overtures, a junior version of Into the Woods, and Frank Rich of The New York Times speaking with the composer for Sondheim on Sondheim on April 28, 2002.[110][113] The two men took their discussion, dubbed "A Little Night Conversation with Stephen Sondheim", on a West Coast tour of different U.S. cities[114][115] including Santa Barbara, San Francisco, Los Angeles,[116][117][118] and Portland, Oregon in March 2008,[119] then to 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".[120][121] Sondheim and Rich had additional conversations: January 18, 2009, at Avery Fisher Hall;[122] February 2 at the Landmark Theatre in Richmond, Virginia;[123] February 21 at the Kimmel Center in Philadelphia;[124] and April 20 at the University of Akron in Ohio.[125] The conversations were reprised at Tufts and Brown University in February 2010, at the University of Tulsa in April,[126] and at Lafayette College in March 2011.[127] 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.'"[128]

On February 1, 2011, Sondheim joined former Salt Lake Tribune theater 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.[129]

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.[130][131]

Sondheim was an avid fan of puzzles and games. He is credited with introducing cryptic crosswords, a British invention, to American audiences through a series of cryptic crossword puzzles he created for New York magazine in 1968 and 1969.[132] 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] Sondheim's 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, Joan Hackett, Raquel Welch, James Mason, James Coburn, Ian McShane, and Richard Benjamin.[133]

Sondheim also wrote occasional music for film: most notably, he contributed five songs to Warren Beatty's 1990 film Dick Tracy, including the ballad "Sooner or Later (I Always Get My Man)", sung in the film by Madonna, which won the Academy Award for Best Original Song. He also contributed to Reds (1981) (both to the score, and with the song "Goodbye for Now"), The Seven-Per-Cent Solution (1976) ("The Madam's Song", later recorded as "I Never Do Anything Twice"), Stavisky (1974) (writing the score), and The Birdcage (1996) ("Little Dream", and the eventually-cut "It Takes All Kinds"). For the 2014 movie adaptation of Into the Woods, Sondheim wrote a new song for the character of The Witch (played by Meryl Streep) entitled "She'll Be Back", which was eventually cut from the film.

Sondheim collaborated with Company librettist George Furth to write the play Getting Away with Murder in 1996, though the Broadway production closed after 31 previews and only 17 performances.[134]

In 2003, he was invited to serve as guest curator for the Telluride Film Festival.[135]

After he was mentored by Oscar Hammerstein II[17] Sondheim returned the favor, saying that he loved "passing on what Oscar passed on to me".[23] In an interview with Sondheim for The Legacy Project, composer-lyricist Adam Guettel (son of Mary Rodgers and grandson of Richard Rodgers) recalled 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".[136]

Sondheim also mentored a fledgling Jonathan Larson, attending Larson's workshop for his Superbia (originally an adaptation 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."[137]

Around 2008, Sondheim approached Lin-Manuel Miranda to work with him translating West Side Story lyrics into Spanish for an upcoming Broadway revival.[138][139] Miranda then approached Sondheim with his new project Hamilton, then called The Hamilton Mixtape, which Sondheim gave notes on.[139][140] 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.[140]

Sondheim provided a voice cameo for the 2021 film adaptation of Tick, Tick... Boom!, directed by Miranda, for the scene in which a fictionalized version of himself leaves a phone message. Sondheim worked on a revised text of the message and voiced it himself after Bradley Whitford, who portrays him, was unavailable to re-record the line.[141]

A supporter of writers' rights in the theater industry, Sondheim was 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 of the non-profit organization until 1981.[142]

Several benefits and concerts were performed to celebrate Sondheim's 80th birthday in 2010. Among them were the New York Philharmonic's March 15 and 16 Sondheim: The Birthday Concert at Lincoln Center's Avery Fisher Hall, hosted by David Hyde Pierce. The concert included Sondheim's music, performed by some of the original performers. Lonny Price directed, and Paul Gemignani conducted; performers included Laura Benanti, Matt Cavenaugh, Michael Cerveris, Victoria Clark, Jenn Colella, Jason Danieley, Alexander Gemignani, Joanna Gleason, Nathan Gunn, George Hearn, Patti LuPone, Marin Mazzie, Audra McDonald, John McMartin, Donna Murphy, Karen Olivo, Laura Osnes, Mandy Patinkin, Bernadette Peters, Bobby Steggert, Elaine Stritch, Jim Walton, Chip Zien, and the 2009 Broadway revival cast of West Side Story. A ballet was performed by Blaine Hoven and María Noel Riccetto to Sondheim's score for Reds, and Jonathan Tunick paid tribute to his longtime collaborator.[203][204] The concert was broadcast on PBS' Great Performances show in November,[205] and its DVD was released on November 16.

Sondheim 80, a Roundabout Theatre Company benefit, was held on March 22. The evening included a performance of Sondheim on Sondheim, dinner and a show at the New York Sheraton. "A very personal star-studded musical tribute" featured new songs by contemporary musical-theatre writers. The composers (who sang their own songs) included Tom Kitt and Brian Yorkey, Michael John LaChiusa, Andrew Lippa, Robert Lopez and Kristen Anderson-Lopez, Lin-Manuel Miranda (accompanied by Rita Moreno), Duncan Sheik, and Jeanine Tesori and David Lindsay-Abaire. Bernadette Peters performed a song which had been cut from a Sondheim show.[206][207]

An April 26 New York City Center birthday celebration and concert to benefit Young Playwrights, among others, featured (in order of appearance) Michael Cerveris, Alexander Gemignani, Donna Murphy, Debra Monk, Joanna Gleason, Maria Friedman, Mark Jacoby, Len Cariou, BD Wong, Claybourne Elder, Alexander Hanson, Catherine Zeta-Jones, Raúl Esparza, Sutton Foster, Nathan Lane, Michele Pawk, the original cast of Into the Woods, Kim Crosby, Chip Zien, Danielle Ferland, and Ben Wright, Angela Lansbury, and Jim Walton. The concert, directed by John Doyle, was co-hosted by Mia Farrow; greetings from Sheila Hancock, Julia McKenzie, Milton Babbitt, Judi Dench, and Glynis Johns were read. After Catherine Zeta-Jones performed "Send in the Clowns", Julie Andrews sang part of "Not a Day Goes By" in a recorded greeting. Although Patti LuPone, Barbara Cook, Bernadette Peters, Tom Aldredge, and Victor Garber were originally scheduled to perform, they did not appear.[208][209]

A July 31 BBC Proms concert celebrated Sondheim's 80th birthday at the Royal Albert Hall. The concert featured songs from many of his musicals, including "Send in the Clowns" sung by Judi Dench (reprising her role as Desirée in the 1995 production of A Little Night Music), and performances by Bryn Terfel and Maria Friedman.[210][211]

On November 19 the New York Pops, led by Steven Reineke, performed at Carnegie Hall for the composer's 80th birthday. Kate Baldwin, Aaron Lazar, Christiane Noll, Paul Betz, Renee Rakelle, Marilyn Maye (singing "I'm Still Here"), and Alexander Gemignani appeared, and songs included "I Remember", "Another Hundred People", "Children Will Listen", and "Getting Married Today". Sondheim took the stage during an encore of his song, "Old Friends".[212][213]

To honor Sondheim's 90th birthday, The New York Times published a special nine-page Theater supplement on March 15, 2020, featuring comments by "Critics, Performers and Fans on the Bard of Broadway."[214] Due to theater closures during the COVID-19 pandemic, the Broadway revival of Company set to open March 22, 2020, Sondheim's 90th birthday, was ultimately delayed.[215] However, the virtual concert Take Me to the World: A Sondheim 90th Birthday Celebration was livestreamed on the Broadway.com YouTube channel on April 26. Participants in the event included Lin-Manuel Miranda, Steven Spielberg, Meryl Streep, Nathan Lane, Mandy Patinkin, Victor Garber, Bernadette Peters, Patti LuPone, Neil Patrick Harris, Jake Gyllenhaal, Christine Baranski, Sutton Foster, Josh Groban, Ben Platt, Brandon Uranowitz, Katrina Lenk, Kelli O'Hara, Jason Alexander, Brian Stokes Mitchell, Beanie Feldstein, Audra McDonald, Laura Benanti, and Raúl Esparza.[216][217][218] After New York City theaters eventually reopened in 2021, Sondheim attended revivals of two of his musicals: the opening night of Assassins at the Classic Stage Company on November 14, and the first post-shutdown preview of Company at the Jacobs Theatre on November 15.[37][219]