Stephen Sondheim: From Musical Theater Master to Pop-Culture Tastemaker

brent johnson and jonathan elliott explore how Stephen Sondheim — who will appear at a rare Q&A in Connecticut this weekend — has slowly been accepted into the mainstream …

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Some of the biggest surprises in popular culture come in the reversal of “cool” — when something that starts off small and cultish becomes fervently embraced in the mainstream. With unexpected quickness, comic books shed their nebbish charm and blossom into multi-million-dollar blockbusters. The walled-off English foreboding of Downton Abbey gives way to intercontinental sensation. And the very specific niche of the musical theater nerd finds acceptance in the pop world at large.

Legendary Broadway composer Stephen Sondheim will appear at a rare Q&A at the Ridgefield Playhouse in Connecticut tomorrow night.
Photo: Jerry Jackson

And that’s exactly where we are now: Starting with 2002’s Oscar-winning adaptation of Chicago and fully arriving in 2009 with the TV phenomenon called Glee, musicals are once again front and center in American pop culture.

Along the way, a parallel explosion has happened to theater’s greatest living creator. For the first time, it’s suddenly cool — almost mainstream cool — to like Stephen Sondheim.

Tomorrow night, the 82-year-old composer will make a rare public appearance, partaking in a public conversation and intimate Q&A at the Ridgefield Playhouse in Ridgefield, Conn. — an hour’s drive from New York City. Sondheim will talk about his five-decade career that has so far included eight Grammys, a record seven Tonys, an Oscar, and a Pulitzer Prize — as well as credits that include West Side Story, Gypsy, Sweeney Todd, and the pop standard “Send In The Clowns.”

“When you have an iconic figure such as Stephen Sondheim coming to a small non-profit performing arts center, it’s definitely a big deal,” says Allison Stockel, the Playhouse’s executive director. “This man has written a tremendous amount of music and worked with some of the most unbelievable people in the industry.”

Still, not everyone knows Broadway the way they did 60 years ago. For much of his career, Sondheim has been an icon of a counterculture. He has been the composer most cherished by the most ardent of theater geeks — if you understood Sondheim, you were a member of an insular club. He has been the hero of an ivory-tower high art form — one the mainstream knew only passingly.

But over the last few decades, that has slowly changed. In 1990, he wrote songs for Warren Beatty’s film adaptation of Dick Tracy — with Madonna singing the tune that won Sondheim his Academy Award: “Sooner Or Later.”

Soon, Krusty the Klown was crooning Sondheim’s most famous song on The Simpsons.

More recently, Tim Burton made Sweeney Todd into a hit movie. Nearly every episode of Desperate Housewives was titled after a Sondheim tune (creator Marc Cherry is an outspoken fan). Even Stephen Colbert has treated Comedy Central viewers to his own versions of the man’s music.

And last week, the show-stopping number from Sondheim’s 1970 musical Company — “Getting Married Today” — reached a huge new audience when it was performed in a scene essential to a season-long plot on Glee.

“It’s more okay to be someone who enjoys a niche than ever,” explains Ilana Lucas, a Princeton- and Columbia-educated Sondheim scholar and an English Department faculty member at Centennial College in Toronto. “There’s geek pride, ‘freak’ pride, fandom pride, musical theater pride. Because of the Internet, among other social forces, small communities actually found out that they’re larger than they thought.”

Sondheim, of course, has always been a complicated artist. The same quality that critics and cult fans love about him is also part of the reason his work has long struggled to be universally popular: complexity.

“What makes Sondheim challenging is that is that he doesn’t rely on hooks or repeated melodies to soothe an audiences,” says Jordan Mann, a musical theater lyricist and teacher, whose musical Trails opens in Seattle in March. “He asks the audience to listen and focus on the words and music. He doesn’t allow the listener to relax.”

Sondheim got his big break in 1957 as a lyricist, putting words to the music of others in West Side Story and then Gypsy.

By the early 1960s, Sondheim started writing both the words and music to his shows. His lyrics were acclaimed for being layered with wit and humanity — focusing often on darker subjects than Broadway was accustomed to. And his music was noted for being unpredictable, with strange chord progressions and jilting melodies. Take “Finishing The Hat” from Sunday In The Park With George, which in 1984 became one of only eight musicals in history to be awarded a Pulitzer. (Yes, that’s Mandy Patinkin — Saul from Homeland and Inigo Montoya from The Princess Bride — singing.)

That complexity is the reason Sondheim is one of the the musical theater composers most celebrated by artists in other genres. His 1973 show A Little Night Music is often performed in opera houses. Rock musicians have praised the uniqueness of his work. Alt-rocker Mike Doughty, the former frontman of Soul Coughing, covered “Send In The Clowns” on his most recent album.

Adding to the allure, Sondheim’s subject matters are diverse and sometimes jarring: Company focuses on the troubles of marriage, 1979’s Sweeney Todd centers on a murderous 19th century barber, 1990’s Assassins gives voice to a collection of people who aim to murder American presidents.

“Sondheim, though not by himself, helped take us into a different era of musical theater,” Lucas says. “An era of ‘serious’ or ‘thoughtful’ musical theater.

“With Sondheim’s pieces, you couldn’t just stand there and sing. You had to be an accomplished actor, and an intelligent one. Sondheim’s pieces are about both the frustration and beauty of being human.”

But sometimes, that has fallen flat with audiences. In 1964, Anyone Can Whistle closed after just nine performances. In 1981, Merrily We Roll Along ended after only 16 — though it has since developed a cult following. Its showstopper, “Franklin Shepard Inc.” — about the friendship of two songwriters unraveling on live television — is one of Sondheim’s most fun and heartbreaking numbers, a dazzling workout that shows off an actor’s talents.

Meanwhile, aside from early hits like West Side Story, Sondheim’s work only occasionally slipped into the mainstream. In 1975, “Send In The Clowns” — a ballad from A Little Night Music — became a Top 40 pop hit for Judy Collins. Frank Sinatra also performed a notable cover.

But none of Sondheim’s shows were household-name hits, like Cats and Phantom Of The Opera by Andrew Lloyd Webber or Godspell and Wicked by Stephen Schwartz.

Then came 2007, when director Tim Burton transformed Sweeney Todd into the first blockbuster adaptation of a Sondheim work. It featured stripped-down orchestration to allow for a filmed plot and the fair thinner voices of Johnny Depp and Helena Bonham Carter — all with the blessing of Sondheim himself. Depp ended up scoring an Oscar nod for the role.

And then there’s Neil Patrick Harris, who might have been condemned to life as a former child star, if not for his formidable vocal chops being put to good use as Tobias in 2000 in a Los Angeles concert production of Sweeney Todd.

That led to his turn as the Balladeer in the 2004 revival of Assassins. And now, Harris is a legitimate star, a song-and-dance-man who has hosted the Tony Awards multiple times.

But the most shocking Sondheim acolyte of all may be Stephen Colbert. In 2010, the deadpan comedian welcomed the composer as a guest on his Comedy Central talk show. Colbert even serenaded him with a re-worked rendition of “Send In The Clowns.”

And it didn’t stop there. The following year, Colbert played Harry in a revival of Company at Lincoln Center in New York City — a cast that also included Neil Patrick Harris and Jon Crier of Two And A Half Men. A year later, Colbert sang a little Sondheim while hugging a bear on a Comedy Central telethon. (Yes, you read that right. Proof is below.)

More than anything, though, Sondheim’s rising mass appeal may be attributed to what might be called “the Glee effect.” Those marginalized, occasionally homosexual theater nerds who worshiped Sondheim in their youth have grown up to run substantial corners of the music, film and television industries. Glee creator Ryan Murphy — who has spoken openly about being a gay, ostracized theater geek — is now a TV tastemaker by creating a show that celebrates musicals and theatricality.

Glee has featured several Sondheim songs as major plot points. Kurt Hummel (Chris Colfer) was accepted to a major New York conservatory after a performance of “Being Alive” from Company. The single charted highly on iTunes after the broadcast.

Glee, horrible as it has become, I believe both made it more okay to like to sing, more acceptable in this ironic age to burst out in song, and became a gateway drug for younger audiences less familiar with Sondheim,” Lucas says. “Maybe someone tuned in for ‘No Air’ [the pop hit by Jordin Sparks and Chris Brown] and left singing ‘Everything’s Coming Up Roses’ [from Gypsy]. It’s all about shifts in social conception.”

Next up for Sondheim? Rob Marshall — the director who brought Chicago to the big screen — is reportedly working on a film version of Into The Woods, the 1987 Tony-winning twist on fairy tales. Meryl Streep is apparently in talks to appear as the Witch — a role famously portrayed onstage by Bernadette Peters and Vanessa Williams.

“I think that as we mature as listeners, we begin to crave complexity and sophistication and wit in our music,” Mann says. “That’s something lacking in pop music and something that musicals can give us. And Sondheim is the apex of the art.”

Stephen Sondheim will appear at the Ridgefield Playhouse in Ridgefield, Conn. He will be interviewed onstage by Emmy-winning journalist Morton Dean and will then take part in a Q&A with the audience. Click here to buy tickets.

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