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20 Stephen Sondheim Songs to Listen to Right Now

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The career of Stephen Sondheim, the celebrated Broadway songwriter who died on Friday at the age of 91, spanned decades and included 20 major productions, including forays into television and film. Here is one song from each of those 20 in chronological order, highlighting a genius that was evident from a jarringly early age (even if critics took a while to catch on) for mixing longing and ambivalence into clever, spiky, dependably unexpected lyrics.

‘What More Do I Need?’

From “Saturday Night,” 1954

Dyspepsia lurks way in the background of “Saturday Night,” his first complete musical (which wouldn’t see a New York stage until almost a half-century later). But in this song, performed here by Liz Callaway, Sondheim depicts a level of dewy-eyed optimism — “Why, I can see half a tree/And what more do I need?” — that will become rare in his later musicals, which tended to pull the rug out on his clearly deluded dreamers. Here is the work of someone barely out of college who can’t believe he is already creating would-be standards.

‘Something’s Coming’

From “West Side Story,” 1957

If this were a list of Leonard Bernstein songs, “Maria” or “Tonight” or “Somewhere” might easily take this spot. But it fell upon Sondheim to depict the inchoate yearnings of a street youth, played by Larry Kert, and offer a plausible glimpse into a mind barely able to glimpse it himself. Sondheim spent the next 60-plus years grumbling about the quality of his “West Side Story” lyrics: the unintelligible passages, the too-clever-by-half internal rhymes. We should all be so flawed.

‘Rose’s Turn’

From “Gypsy,” 1959

How to pick just one song from what many consider is the greatest musical ever? None other than Cole Porter gasped at one of Sondheim’s lyrics in “Together, Wherever We Go,” and “Everything’s Coming Up Roses” earned the 29-year-old a spot in Bartlett’s book of quotations. But it is Ethel Merman’s absolute tour de force — one that, owing to the composer Jule Styne’s previous engagement one fateful night, Sondheim largely willed into being at a rehearsal piano — that gave the clearest example of what lay ahead.

‘Comedy Tonight’

From “A Funny Thing Happened on the Way to the Forum,” 1962

The galumphing opening chords marked the first time Broadway audiences heard Sondheim’s music as well as lyrics. And they were this close to instead hearing an opening number called “Love Is in the Air,” which is sprightly and charming and the absolute wrong way to kick off an evening of vaudeville turns and eunuch jokes. Luckily, Jerome Robbins caught an out-of-town performance just before its New York transfer and mentioned this to Sondheim, who wrote that weekend the no less hummable “Comedy Tonight,” sung here by Jason Alexander. As exacting as he was with his notes and his words, Sondheim did what he had to do in order to make a show work.

‘Anyone Can Whistle’

From “Anyone Can Whistle,” 1964

There is a frequently cited notion (one that Sondheim just as frequently refuted) that the show’s title song represents the purest, most unadulterated look into his own emotionally stunted psyche. Leaving that aside, the song — performed on the original cast recording by Lee Remick — is a bittersweet oasis in a show stuffed with ideas and set pieces and pastiche numbers and the sorts of Big Ideas that Sondheim would soon learn to convey more adroitly. It’s not all so simple, not by a long shot.

‘We’re Gonna Be All Right’

From “Do I Hear a Waltz?,” 1965

Sondheim didn’t want to go back to solely writing lyrics, and he quickly regretted teaming up with Richard Rodgers, the longtime writing partner of Sondheim’s mentor, Oscar Hammerstein II. One of the collaboration’s many skirmishes involved this song, a wry evisceration of an unhappy marriage that apparently sounded an awful lot like Rodgers’s own. The version that made it to opening night is clever; the one that got tossed, later resurrected and sung here by Jason Danieley and Marin Mazzie, is brilliant.

‘I Remember’

From “Evening Primrose,” 1966

Not even the “I want” song remained intact in Sondheim’s visionary hands. This quirky made-for-TV romance, in which the female lead ruminates on the years she has lived inside a department store and pines to see the sky again, had all but disappeared until Mandy Patinkin invited his “Sunday in the Park With George” co-star Bernadette Peters to record the score with him on a 1990 album. With its trees like broken umbrellas and ice like vinyl, the song is more than a little bit creepy and altogether marvelous.

‘Getting Married Today’

From “Company,” 1970

Possibly the greatest artistic hot streak of the 20th century (take note of the dates on this and the next two entries) began with this quasi-Brechtian look at marriage through the eyes of 35-year-old Bobby, who — maybe, sort of, kind of — wants no part of it. This anxiety-drenched patter song from one of his friends, sung on the original cast album by Beth Howland, doesn’t do much to allay Bobby’s fears. In the process, the already high-bar of Sondheim’s lyrical virtuosity vaulted several notes higher.

‘The Road You Didn’t Take’

From “Follies,” 1971

The word “ambivalence” typically surfaces in a discussion of Sondheim and his themes, with “Company” as Exhibit A. (That score includes the song “Sorry-Grateful.”) But while the “Follies” score is chockablock with such barn burners as “Broadway Baby” and “I’m Still Here,” along with the piercing “Losing My Mind,” this character study, sung on the original cast album by John McMartin, sublimely lays the groundwork for the misgivings to come. And its final two lines — “The Ben I’ll never be/Who remembers him?” — should hang in a museum.

‘Send in the Clowns’

From “A Little Night Music,” 1973

The haunting “Every Day a Little Death” and the virtuosic triptych of lust that is “Now/Soon/Later” would be career-defining works for just about anyone else. But any time Sarah Vaughan, as heard here, and Frank Sinatra and Judy Collins and Barbra Streisand and Judi Dench and Krusty the Clown of “The Simpsons” can agree on anything, let alone a bittersweet rumination on lost love with an oscillating time signature, the choice is obvious.

‘Fear No More’

From “The Frogs,” 1974

As reluctant as Sondheim was to write lyrics for other composers, it was almost unheard of for him to write music for other people’s lyrics. But he made an exception for William Shakespeare (as one tends to do) in this curiosity that debuted in a Yale University swimming pool and reached Broadway 30 years later. In this adaptation of an Aristophanes comedy, Shakespeare squares off against George Bernard Shaw in an agon, the high-stakes debate that was common in ancient Greek comedies; Sondheim’s gossamer arrangement of this soliloquy from “Cymbeline,” sung here by George Hearn, helps earn the Bard a ticket out of the underworld.

‘Someone in a Tree’

From “Pacific Overtures,” 1976

Sondheim described the frequent request to name a favorite of his own songs as “understandable but unanswerable.” Still, he repeatedly answered it anyway by suggesting this prismatic song, in which an eyewitness and an earwitness give markedly different accounts of a meeting (accounts that are muddied further by the re-recollections of the eyewitness as an old man). Perhaps it was his wish to essentially elevate his audiences to collaborators: Whether high up in a branch or seated in a Broadway theater, the very act of experiencing something makes that thing real (“Without someone in a tree/Nothing happened here”).

‘A Little Priest’

From “Sweeney Todd,” 1979

Seconds before this song, the titular “Demon Barber of Fleet Street” has morphed from a revenge seeker into an indiscriminate psychopath in the bruising aria “Epiphany.” Only one song remains before intermission. How could the tension possibly heighten even further? It can’t, and so Sondheim (and book writer Hugh Wheeler) instead puncture it with an uproarious one-liner from Sweeney’s murderous counterpart, Mrs. Lovett, followed by a ghoulish list song — possibly the greatest of Act I finales — in which the two, here Angela Lansbury and Len Cariou on the original cast album, make macabre sport of listing the various individuals they plan to grind into meat pies.

‘Good Thing Going’

From “Merrily We Roll Along,” 1981

What do you call a recapitulation whose narrative unspools backward? A precapitulation? The DNA of this sadder-but-wiser lament can be found throughout the show, including in an earlier (or later, by the show’s logic) up-tempo iteration and in the evening’s very first (which makes it the very last) piece of music, a high school commencement song. But the third (first?) time is the charm, complete with a devastating and just-flashy-enough final line that helped turn it into a crossover hit for Sinatra, heard here.

‘Finishing the Hat’

From “Sunday in the Park With George,” 1984

Seeing as Sondheim named not one but two books after this song (the second edition is called “Look, I Made a Hat,” and both are essential reading), it clearly had significance for him. As a teenager, I thought this depiction of creation — and the combination of rigor and abandon that it requires — ended on a note that was equal parts proud and rueful. How wrong I was about the rueful part. And the immensity of “What you feel like, planning a sky,” sung here by Mandy Patinkin, will never dissipate.

‘On the Steps of the Palace’

From “Into the Woods,” 1987

So many of the most astonishing moments in Sondheim’s lyrics come from decisions made then and there: young Gypsy Rose Lee finding her voice mid-striptease, Bobby in “Company” resolving to be alive by not being alone, Sweeney Todd settling on the idea of mass slaughter. Perhaps the most beguiling is this number, in which Cinderella, played here by Kim Crosby, turns the act of leaving her glass slipper behind into a conscious choice. Sondheim credited his “Woods” book writer, James Lapine, for the idea, but the sparkling execution is his alone.

‘The Ballad of Booth’

From “Assassins,” 1990

More than 30 years into a convention-shattering career, Sondheim still raised eyebrows when he announced he was about to musicalize the likes of John Hinckley Jr. and John Wilkes Booth. Some of those eyebrows never totally lowered: A Broadway revival was postponed in the wake of 9/11. But this early set-piece, in which Booth (Victor Garber, joined by Patrick Cassidy as the Balladeer) mashes up grandiose poetry, self-pity, cogent criticism and vile racism in a plaintive cri de coeur, went a long way toward reminding audiences that they were in very good and very frightening hands.

‘What Can You Lose?’

From “Dick Tracy,” 1990

Madonna’s slinky “Sooner or Later” may have won the Academy Award, and “More” may be more chockablock with musical theater Easter eggs. But it’s this Harold Arlen-inspired song of unrequited love that gives Warren Beatty’s rather cluttered film the closest thing to a heartbeat. Sondheim’s original duet has become a heart-rending solo for the likes of Audra McDonald, Gavin Creel and, from his virtual 90th-birthday celebration, Judy Kuhn.

‘Loving You’

From “Passion,” 1994

“Passion” was the first musical I saw (and saw again and again) in its original run. And those initial audiences hated Fosca, the grasping, manipulative, unprepossessing third point of the show’s love triangle. This song comes late in the piece, just as she reappeared in a way that had people around me snickering and groaning at the mere sight of her. These 135 seconds — one of Sondheim’s simpler melodies — changed pretty much everything. Fosca, played here by Donna Murphy, was every bit as suffocating as before, and maybe even more baffling. She was also a heroine.

‘Isn’t He Something!’

From “Road Show,” 2008

This show — which started as “Wise Guys” and then became “Bounce” before settling as “Road Show,” each time with a starry new director and a commensurate lurch in direction — went through very public growing pains, including an ill-fated reunion with Hal Prince and lawsuits with Scott Rudin. This melancholy charmer, sung by a doting mother (here, Alma Cuervo) about her ne’er-do-well son, entered the show’s ever-changing song stack fairly early on and remained a high point each step of the way.

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