[1] With his frequent collaborators Harold Prince and James Lapine, Sondheim's Broadway musicals tackled unexpected themes that ranged beyond the genre's traditional subjects, while addressing darker elements of the human experience.

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).

[29] "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.

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.

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.

Sondheim agreed, but Ethel Merman – cast as Mama Rose – had just finished Happy Hunting with an unknown composer (Harold Karr) and lyricist (Matt Dubey).

A show about a single man and his married friends, Company (with a book by George Furth) lacked a straightforward plot, instead centering on themes such as marriage and the difficulty of making an emotional connection with another person.

[60] 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.

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.

[68] An off-Broadway revival starring Jonathan Groff, Daniel Radcliffe, and Lindsay Mendez ran from November 2022 to January 2023 at the New York Theatre Workshop; it moved to Broadway in fall 2023.

Lapine prepared the multimedia production iSondheim: aMusical Revue, which was scheduled to open in April 2009 at the Alliance Theatre in Atlanta; it was canceled due to "difficulties encountered by the commercial producers attached to the project ... in raising the necessary funds".

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

[100] Sondheim began collaborating with David Ives in 2014 on a musical based on the Luis Buñuel films The Exterminating Angel and The Discreet Charm of the Bourgeoisie, initially slated for previews at the Public Theater in 2017.

[102] A November 2016 workshop included Matthew Morrison, Shuler Hensley, Heidi Blickenstaff, Sierra Boggess, Gabriel Ebert, Sarah Stiles, Michael Cerveris, and Jennifer Simard.

[110] 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.

[111][114] The two men took their discussion, dubbed "A Little Night Conversation with Stephen Sondheim", on a West Coast tour of different U.S. cities[115][116] including Santa Barbara, San Francisco, Los Angeles,[117][118][119] and Portland, Oregon in March 2008,[120] then to Oberlin College in September.

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.

[133] Sondheim was "legendary" in theater circles for "concocting puzzles, scavenger hunts and murder-mystery games",[10] inspiring the central character of Anthony Shaffer's 1970 play Sleuth.

In 1975, Perkins said he and Sondheim were working on another script, The Chorus Girl Murder Case: "It's a sort of stew based on all those Bob Hope wartime comedies, plus a little Lady of Burlesque and a little Orson Welles magic show, all cooked into a Last of Sheila-type plot".

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.

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.

[217][218] 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.

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".

[223][224] 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.

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.

Performers at the event included Helena Bonham Carter, Rob Brydon, Petula Clark, Judi Dench, Damian Lewis, Julia McKenzie, Bernadette Peters, and Imelda Staunton.

[235]Luca Prono described Sondheim's work as rejecting the traditional image of the Western world typically presented in Broadway productions, and instead depicting it as "predatory and alienating".

His works have acquired a cult following with queer audiences, and his songs have been adopted as life scores for successive generations of gays, and have often had a primary role in AIDS fundraising events.

"[238]Matt Zoller Seitz characterized Sondheim's work for its bravery to express the truth, in all its complexity: "compassionately but without sugarcoating anything," devoid of the "easy reassurances and neat resolutions" typically demanded in the marketplace.