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Remembering the man behind Company, Into the Woods, and Sunday in the Park With George.

Stephen Sondheim died last week at the age of 91, and there’s too much to say. For most people, it would be enough to be the lyricist and composer behind iconic individual songs like “Being Alive” and “Somewhere.” But Sondheim wasn’t just a clever and affecting songwriter; he wasn’t even just a giant in the world of musical theater — he was the giant, a genius who remade the entire genre in his image.

Sondheim musicals were once considered too cerebral for mainstream pop culture. Now, Sondheim’s songs, many of them rapturous odes to ambiguity, ambivalence, and the mortifying ordeal of being known — have become the gold standard by which onstage emotions are judged. “Isn’t it lovely how artists can capture us?” he wrote in his Pulitzer-winning Sunday In the Park With George (1984), and it’s true: No artist captured people quite like Sondheim.

Vox has gathered our thoughts on the impact of his work, but before we dig into some of our favorite shows, a quick personal note about the person he was.

In her 1999 autobiography, Wake Up, I’m Fat!, actress Camryn Manheim (who famously dedicated her 1998 Emmy win for The Practice to “all the fat girls!”) wrote about how impossible it had been for her to find an agent after Juilliard. Size discrimination was rampant, and Manheim was ignored despite her talent — until she got hired to do readings for Stephen Sondheim. As Manheim told it, Sondheim, after watching her work for a week, asked her to audition for him. When she confessed that she didn’t have an agent, he arranged for her to get one. Manheim never did audition for Sondheim, but thanks to him, she got her career.

As a fat person who’d been told all my life I was too fat to be onstage, having Sondheim show up in the middle of this book as the benevolent patron saint of fat women was a revelation to me. Because Sondheim, my lifelong hero, my own patron saint, had looked at Camryn Manheim and seen all her talent, I felt like he was looking at me, too, encouraging me to live my dreams without shame or fear. After all, if Stephen Sondheim could look past a person’s size, why couldn’t everyone else?

Thank you, Mr. Sondheim, for this, and so much more. —Aja Romano

Into the Woods

Into the Woods was my gateway Sondheim. When I was about 8 years old, my older sister sat me down in front of the PBS recording of the original Broadway cast performance, and together we bopped our way through the infectious nursery rhyme rhythms of the opening number. Cinderella, Jack (of beanstalk fame), and Little Red Riding Hood were all going into the woods in search of their wish, and I was enchanted.

Then my sister left me to watch the rest of the show myself. When she came back a few hours later, she found me much shaken by what I had just witnessed, and ready to rewind the VHS and watch the whole thing again and again and again until I understood it.

A lot of people have similar Into the Woods stories. It presents as unusually accessible for a Sondheim show, even cuddly, so much so that a bowdlerized version of the first act is frequently licensed to schools as Into the Woods Jr. (I made myself very annoying to the director of my middle school production by opining that adding the second act would really make our staging a lot richer.) After all, it’s a fairy tale mashup! With bouncy little songs about beans and cows and such! You can even hum them!

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The 2014 Paris staging of Into the Woods.

But if Into the Woods greets you with open arms, it’s only to hide the vicious points of its claws. That deceptively simple opening theme grows more and more unsettling as it repeats, until Rapunzel’s wordless arpeggios have turned into screams. And the characters’ wishes don’t rebound on them so much as devour them whole.

Sondheim understood something fundamental about fairy tales: that these are stories of grievance and vengeance and lust and the spite that curdles families like bad milk. When Into the Woods tells us that no one is alone, it’s both a comfort and a threat. —Constance Grady

Assassins

I was 13 the first time I saw Assassins. My mother and I, having driven 90 minutes for the privilege, were probably the only people in the audience at Circuit Playhouse in Memphis who knew what we were getting into.

At first, the rest of the audience didn’t quite know what to do with this sketchy, scathing satirical drama about the marginalized men and women who try to kill presidents in America, but by the time “The Ballad of Booth” was over, they figured it out. Sondheim spends the entire song making us sympathize with a racist, conspiracy-mongering narcissist, but at the climax, he reminds us exactly who we’re in league with by having John Wilkes Booth drop a racial slur. It hit the audience like something physical, exactly as it should.

We talk about the power of theater in the abstract, but Assassins impacted me in a very concrete way, more profoundly than any other single piece of media in my life. The ability of Sondheim and librettist John Weidman to both sympathize with and condemn their ensemble of historical outcasts, all while interrogating the larger social systems that failed them, taught me what deep, clearsighted empathy really looks like.

Assassins doesn’t always work — its contradictions, its tripwire of Grand Guignol and pathos, can lead to productions that miss the point completely. But when Assassins works, it devastates. There’s a reason Assassins failed twice to come to Broadway: first, in 1990, when it debuted off-Broadway just before the Gulf War began and was deemed too anti-patriotic; then, in fall 2001, when it was canceled before opening. Assassins is often too uncomfortable, too painful to bear — which is exactly why, as our assassins observe, attention must be paid. —AR

Sunday in the Park With George

Sunday in the Park With George, the 1984 musical for which Sondheim won the Pulitzer Prize for Drama (alongside collaborator James Lapine), is about two kinds of artistic burdens.

The first act, which follows pointillist Parisian painter Georges Seurat as he creates his 1886 masterpiece A Sunday Afternoon on the Island of La Grande Jatte, is about the burden of genius. Seurat (who has been memorably played by Mandy Patinkin, Daniel Evans, and Jake Gyllenhaal, among others) becomes so consumed with creating an image that captures a singular moment in time that he shuts out the world, including his girlfriend, Dot.

The second act follows Seurat’s great-grandson in 1984. He constructs elaborate, experimental art installations that nobody seems too excited by, and he spends more time trying to find funding for his work than his great-grandfather had to. This act, then, is about the burden of realizing the limits of your own imagination, of understanding that you might not be a genius after all, or at least that what’s in your head will never quite translate into reality.

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Actress Annaleigh Ashford as Dot in Sunday in the Park With George, 2017.

Sunday is stacked with some of Sondheim’s greatest songs. The first-act standout “Finishing the Hat” (often spoken of as Sondheim’s single best song) depicts Seurat as he works to get a relatively minor detail — a hat — exactly right in his painting, isolating himself from the rest of the world in the process. “Children and Art” sees an elderly Dot contemplating the only two true legacies a person might leave behind. (They’re in the title.) “Color and Light,” “Putting It Together,” “Move On” — I could go on.

Yet I keep coming back to “Sunday.” The song shows the final assembly of A Sunday Afternoon, Seurat moving his various pieces around to create the painting we know today. It’s deeply, achingly beautiful, and the effect onstage of actors coming together to replicate the famous image is staggering. The music and lyrics somehow capture the feeling of light trickling through the treetops, frozen for eternity. It’s the song hundreds of Broadway performers gathered to perform as a memorial to Sondheim, and with good reason: The song feels like legacy, an unforgettable echo passed down through the ages. —Emily VanDerWerff

Company (or, Original Cast Recording: Company)

Company had made its 1970 Broadway debut only a week prior when the cast gathered in a studio to record the original cast album. An orchestra was there, too. So was the show’s director Hal Prince, playwright George Furth, and composer, a 40-year-old Stephen Sondheim. Serendipitously, so was pioneering documentarian D.A. Pennebaker.

Pennebaker, perhaps best known at that point for having made the 1967 Bob Dylan film Dont Look Back, had been brought in to film the recording session as a potential pilot for a TV series about different cast album recordings. But, as Pennebaker recounts in a humorous text crawl at the start of the film, that show never happened. The pilot remains a stand-alone film.

Original Cast Album: Company is a jewel of musical documentaries, capturing the cast’s incredible performances with the kind of close-up detail you can’t get when you’re down in the seats and they’re onstage. Most notable is Elaine Stritch’s grueling, yowling marathon recording of “Ladies Who Lunch.”

Yet somehow Sondheim manages to steal the show whenever the camera turns to him. He exudes some mixture of amusement, exhaustion, and quiet agony when he hears a rhythm go off just a little. He tries to get Pamela Myers to pronounce “Bobby bubi” correctly, an imperceptible difference to most ears; he catches notes that have crept out of line; he watches with anxious confidence as Beth Howland hurtles herself through the breakneck “Getting Married Today.” He knows this cast can do it — they’ve been doing it onstage — but ever the perfectionist, he won’t take his foot off the pedal until he’s sure it’s worthy of committing to vinyl.

Company, among the earlier shows for which he wrote both music and lyrics, was also one of the first on Broadway to center on adult relationships and mature themes. There are ways in which it’s aged weirdly, and others in which it feels like Sondheim wrote it yesterday. “Being Alive,” both in the show and in the movie, is so moving it makes your heart want to explode out of your chest — a testament to Sondheim’s uncanny grasp of the perplexities and weird, wonderful joys of just being a person in the world. The film offers a glimpse into the kindly exacting, genially unrelenting drive for perfection for which his collaborators loved him. —Alissa Wilkinson

Sweeney Todd: The Demon Barber of Fleet Street

My love for Sondheim blossomed immediately, despite my first encounter being an extremely high school production of Sweeney Todd: We tried to replicate a Broadway chorus using some ambitious teenagers with fake beards and … me, in a makeshift orchestra pit, staring down a trumpet part rewritten for xylophone. (It was still better than the Tim Burton version.)

Sweeney Todd — a tragicomedy about a mythic serial killer — has given Sondheim a certain macabre reputation, despite his many proudly quotidian musicals. But Sondheim knew that people want to see the pure expression of emotion in a musical, and that there are plenty of ones worth exalting besides joy and sorrow. In Sweeney, he summoned a monster to swallow up all our fears of change and of staying the same. Not to mention fears of, well, being chopped into bits.

The grand theatrics are still a bit of a departure. The ordinary people Sondheim is known for appear here only as a faceless chorus and bit-part fools; they feed the cruel machine of the Industrial Revolution. The main figures are larger-than- life oddballs: a barber with a mysterious past, an obsessive judge, a hardscrabble pie-maker. Dense music and lyrics often abruptly shift in cadence, dancing around the inevitable bloodletting; medleys usher victims into the barber chair even as they chatter and croon about their dreams.

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Actors Patti LuPone, Michael Cerveris, and Alexander Gemignani onstage in the 2005 Broadway staging of Sweeney Todd.

The lighter Sondheim touch is thankfully present throughout; there are some quiet, lovely songs (“By the Sea”), and almost every scene is leavened by the wit of the bumbling yet cunning pie-maker, Mrs. Lovett. The highlight is one of her duets with Sweeney, “A Little Priest,” in which Sondheim delivers on the impossible task of coming up with new twists on all the puns you might expect from the start of the musical.

Still, depending on your feelings about musicals that are really operas, it may all seem a bit much by the second reprise of a ballad sung to some shaving knives. That was definitely the vibe I got from confused friends who showed up to a high school musical about Victorian cannibalism. (The next production chosen was The Pajama Game, and I think our suburban principal let out many sighs of relief.) But if the world is “man devouring man, my dear,” then, as the demon barber himself asks, “who are we to deny it in here?” —Tim Williams

And some of Dorsey’s personal plans and interests gave external critics more reasons to push for his replacement in recent years. Dorsey famously wanted to leave Silicon Valley to move to Africa for at least three months in 2019 (he later scrapped those plans), and for the past few years, he began devoting more of his time to developing a new decentralized social media ecosystem, Bluesky. In Dorsey’s tweets and public interviews over the past few years, he’s spent more time talking about Bluesky, crypto, blockchain, and other related decentralized internet endeavors than growing Twitter’s main product itself.

Elliott Management group made Dorsey’s divided attention the backbone of its failed attempt to push Dorsey out of the company last year.

Still, despite these challenges, Dorsey is leaving Twitter in a place of relative strength compared to even a year ago. In recent months, Twitter has been monetizing more of its products at a rapid pace beyond just advertising, introducing tools like Twitter Blue, a paid subscription version of the platform. And the company’s earnings the past few quarters have been relatively strong.

“Jack says he is choosing the company over his own ego, but I think this is about as good as it gets for the company — and he is leaving being able to say the stock was up,” one former Twitter executive told Recode. The source also said that Dorsey trusts the new CEO Agrawal, who has executed his vision so far. “Leadership change always gives engineers a reason to freak out … so putting a CTO in place keeps the engineers placated and maintains the steady, iterative product direction Jack oversaw.”

Dorsey stepped down as Twitter CEO once before, after being pushed out by his board in 2008, only to have a Steve Jobs-style return in 2015. It seems less likely, though, that he would return a second time.

There’s a lot we still don’t know about the leadership switch at Twitter. In the coming weeks, we should expect to find out more about the circumstances around Dorsey’s exit and how the company might change under Agrawal.

But what’s most clear now is that Dorsey’s exit is another example of a trend at other significant tech companies. As my colleague Peter Kafka wrote earlier this year when Amazon founder Jeff Bezos said he’d step down from his CEO role, Big Tech has gotten so big that it no longer needs its demigod-like startup founders at the helm. Bezos, Steve Jobs of Apple, and Sergey Brin and Larry Page of Google all turned over their companies to trusted stewards with more low-key personas — and those companies are still financially doing great.

The exception to that is Mark Zuckerberg, the tech founder CEO who seems to have no plans to step down, even though he and his company are perpetually mired in scandal. Unlike Dorsey, Zuckerberg has been rewarded by Wall Street for his relentless focus on growing his company’s profits. And also unlike Dorsey, Zuckerberg managed to negotiate unilateral control over his board from the very beginning.

Dorsey could still be in charge if he had more power over Twitter’s board or if he grew the company at an expansive scale like Facebook.

But instead, Twitter will move into a new era — one without an eccentric, wizard-bearded leader who trolled Congress and waxed poetic about the future of the decentralized web. The Dorsey years may not have been the most focused, but they were memorable.

Peter Kafka contributed reporting to this article.

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