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The 6 Best Sondheim Movies to Help Dim the Lights on the Broadway Legend

The master of internal rhymes, unhappy endings, and discordant melodies died Friday at 91. Here's how to mourn with a movie marathon.

Stephen Sondheim

Stephen Sondheim


The final curtain has fallen on Stephen Sondheim, maestro of American musical theater, who died at 91 on Friday. The brilliant mind behind “Into The Woods,” “Sweeney Todd,” “Company,” “Sunday in The Park With George,” and many, many more was a titan of Broadway, and the last living connection to the golden age of musicals. As a film critic, my early cinematic experiences began with musical movies, including filmed stage versions of “Into The Woods,” “Gypsy,” and of course, “West Side Story,” for which a very young Stephen Sondheim wrote the lyrics (same for “Gypsy.”)

It set me up for a lifetime of appreciating high drama, grand spectacle — and the unlikely comedic potential of cannibalism.

As last year’s Zoom-ified 90th birthday celebration for Sondheim proved, performing his songs is no small task. Numbers like “Send in The Clowns,” “Ladies Who Lunch,” and “Being Alive” are five-act plays in and of themselves, and as such have been interpreted and re-interpreted by every musical theater performer worth the price of a Broadway ticket. Powerhouse divas like Elaine Stritch, Bernadette Peters, and Angela Lansbury owe much of their career-defining work to Sondheim. Watching a singer grapple with the precision of his lyrics, emotional arcs of his songs, and unusual rhythms of his music separates the standing ovation-worthy from mere mortals.

While we’ll be waiting awhile for Richard Linklater’s “Merrily We Roll Along,” filmed over a 20-year span to follow the chronology of the show, there are plenty of screen versions of Sondheim’s work available to stream today. Here are six of the best, with notes on where to find them.

To borrow from “Company” scene-stealer Joanne: Let’s all drink to that.

“West Side Story” (1961)

One of the greatest movie musicals ever made, the original “West Side Story” is getting a contemporary remake from Steven Spielberg in two weeks. “West Side Story” features a book by Arthur Laurents, music by Leonard Bernstein, and lyrics by Sondheim, who was just 27 years old when “West Side Story” premiered. A brilliant lyricist from the start, his fingerprints are all over the clever songs, easily recognizable in lines like: “I like the isle of Manhattan/Smoke on your pipe and put that in.” The upbeat “Gee Officer Krupke” is a rare bop from the king of malaise, his comedic chops shine in collaboration with Bernstein’s more traditional melodies.

Available on HBO Max and to rent on Amazon Prime, Apple and other services. The Spielberg remake opens in theaters on December 10. 

“Sweeney Todd: The Demon Barber of Fleet Street” (2007)

One of Sondheim’s darkest works (rivaled only by “Assassins”) was introduced to a global audience in 2007, courtesy of Tim Burton. The director cast his frequent collaborator Johnny Depp as the murderous barber, and Helena Bonham Carter as Broadway’s Lady MacBeth, Mrs. Lovett. Though the stars, not known for their singing, struggled with one of Sondheim’s more difficult scores (it is, after all, an operetta), Burton’s commercial take on the cannibalistic story proved to be the perfect marriage of sensibilities. A hit with critics and audiences, the film is one of Hollywood’s better musical adaptations in recent memory.

Available to stream on Hulu, Paramount+, Amazon Prime, and other services. 

“Original Cast Album: Company” (1970)

original cast album company

“Original Cast Album: Company”

Shot in black and white for an unfinished series, D.A. Pennebaker’s beloved cult classic takes you behind-the-scenes inside the recording studio for the original Broadway cast album of “Company,” one of Sondheim’s most brilliant and enduring works. Documentary lovers came to the film for Pennebaker, and musical theater lovers came for Elaine Stritch’s iconic breakdown as she muscled through the recording of “Ladies Who Lunch.” The movie also features unprecedented footage of Sondheim giving notes, which could be notoriously exacting. God bless Donna McKechnie for pronouncing “bubbi” for the man. The film was unavailable for decades, an oversight recently corrected by Criterion. (For a perfect double feature, pair it with the “Documentary Now” episode “Co-op: Original Cast Album,” set in a New York City co-op.)

Available to stream on Criterion. “Documentary Now” available on Netflix. 

“Best Worst Thing That Ever Could Have Happened” (2016)

Lonny Price’s documentary about the original production of “Merrily We Roll Along” is an intimate portrait of one of Sondheim’s greatest heartbreaks. “One of the lessons of adulthood is disappointment,” says a bleary-eyed actress who muses on her time in “Merrily,” a notorious 1981 flop for Sondheim and Hal Prince that ended their decades-long collaborative friendship. The nostalgic documentary chronicles the dashed hopes and dreams of the young performers who thought they had landed their big Broadway break, only for the show to close after  sixteen performances. “Merrily” has since been re-evaluated, and will someday hopefully be fully redeemed by the aforementioned Linklater adaptation. But “Best Worst Thing” offers a historical reminder that Sondheim wasn’t always as universally beloved as he is today.

Available on Netflix. 

“Into The Woods: Original Broadway Cast” (1987)

To fully understand Bernadette Peters, one must see her Sondheim. Though she had fun screen roles in “The Jerk” and “Mozart in The Jungle,” Peters is a true Broadway icon in the vein of — well, they just don’t make ’em like Bernadette anymore. Kristen Chenoweth can try to emulate her bubbly lilt, but she’ll never be able to ruin a rutabaga with such panache. Sorry to Meryl, but she doesn’t even come close in the 2014 big screen version. Probably Sondheim’s biggest commercial hit, and his most accessible show, nothing beats the original Broadway cast of “Into The Woods.” It’s a miracle we even have access to this 1987 stage version — it’s very rare for a film of a Broadway show to make it to the screen.

Available to rent on Apple TV.

“Gypsy” (1972)

Old Hollywood buffs will enjoy seeing Natalie Wood’s Gypsy Rose Lee opposite Rosalind Russell’s Mama Rose, the most iconic Broadway role for a woman ever to be written. Sondheim landed his second lyric-writing gig following his success on “West Side Story,” which impressed the initially hesitant composer Jule Styne enough to take a chance on the kid. It’s no surprise that Sondheim had a hand in one of the greatest musicals of all time, which weaves a devastating show business fable into one powerful story. Vaudeville, burlesque, fame, and the original battle axe stage mother — “Gypsy” has it all. While it’s a tragedy that Ethel Merman’s performance isn’t caught on tape, Russell’s is certainly closer to it than Bette Midler’s 1993 effort.

Available on HBO Max. Midler’s 1993 version is on Amazon Prime.

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