Dear listeners,
Over the weekend, I got to see an absolute songwriting legend in action when I caught Jimmy Webb playing some of his greatest compositions at City Winery in Manhattan.
Even if you don’t know Webb’s name, you certainly know some of his unimpeachable contributions to the American songbook: “Wichita Lineman,” “MacArthur Park,” “By the Time I Get to Phoenix,” “Up, Up and Away,” “The Highwayman” — I could go on. (And I will, in today’s playlist.) The show was a bit like being at a taping for an exceptionally entertaining episode of “VH1 Storytellers.” Webb, 80, was in fine form, sitting at a piano as he regaled the audience with witty anecdotes and star-studded memories of some of the musicians he wrote for, like Glen Campbell, Linda Ronstadt and Frank Sinatra (whom he still refers to, with the ingrained manners of a son of a Baptist minister, as “Mr. S”).
Webb got his start as a songwriter in his late teens when he moved from Oklahoma to Los Angeles and signed a contract with one of Motown’s publishing companies. His star rose quickly: He was barely 21 when the 5th Dimension’s recording of his song “Up, Up and Away” and Campbell’s indelible take on “By the Time I Get to Phoenix” both became smash hits in 1967. Throughout his long and varied career, Webb combined the tradition of Tin Pan Alley craftsmanship with the emerging sensibility of the counterculture, penning expertly detailed and deeply felt songs that reflected their moment but have also sturdily stood the test of time.
Today’s playlist celebrates some of Webb’s greatest and most enduring hits. You’ll hear some belt-able ballads, some country standards and even an underappreciated gem from Webb’s rich discography as a solo artist. (He’s still adding to that discography, too: Last week he released “Yours for the Taking,” an album of previously unreleased material that he wrote for other artists.)
Even if you weren’t lucky enough to see Webb on this tour, you can still experience the next-best thing by watching the latest episode of PBS’s “Great Performances,” which features Webb holding court and playing his classics with some stellar vocalists like Vince Gill, Lyle Lovett and Campbell’s daughter Ashley. And, of course, you can always listen to this playlist.
I hear you singing in the wire,
Lindsay
Listen along while you read.
1. The 5th Dimension: “Up, Up and Away”
Webb struck gold early in his songwriting career with this ever-ascending sunshine-pop smash — made famous by the 5th Dimension — for which Webb won the Grammy for song of the year when he was just 21. “Up, Up and Away” took home five total Grammy Awards in 1968, and for decades it had the distinction of being the single most winning song in Grammy history, until its achievement was tied, in 2025, by a very different song: Kendrick Lamar’s “Not Like Us.” (Amazingly, that is not the only Jimmy Webb-Kendrick Lamar connection; on his 2024 track “TV Off,” Lamar also sampled Monk Higgins’s take on “MacArthur Park.”)
Listen on Spotify, Apple Music or YouTube
2. Glen Campbell: “By the Time I Get to Phoenix”
Of the many, many musicians who have sung Webb’s songs over the years, the one he is probably most closely associated with is the Rhinestone Cowboy himself, Glen Campbell. A teenage Webb was first inspired to write songs after hearing Campbell’s ballad “Turn Around, Look at Me”; as Webb recalls in the PBS special, “I said, ‘That’s the guy I want to sing my songs.’” Webb’s wish came true just a few years later, though he later recalled that the clean-cut Campbell’s first words to him were, “Don’t you think it’s time you got a haircut?”
The wistful 1967 tune “By the Time I Get to Phoenix” was Campbell’s first major hit with a Webb song — and an early example of Webb’s remarkably succinct way with narrative — but it certainly wouldn’t be his last. To say that “By the Time I Get to Phoenix” is often covered is an understatement: BMI listed it as the 20th most performed song of the 20th century. No less an authority than Frank Sinatra has called it “the greatest torch song ever written.”
Listen on Spotify, Apple Music or YouTube
3. The Brooklyn Bridge: “Worst That Could Happen”
This wrenching breakup ballad, first recorded by the 5th Dimension but made into a hit by the pop group the Brooklyn Bridge, is a perfect example of the appeal of Webb’s dynamic melodies to vocalists who love to belt. Webb elevates pop-musical pomp to the level of orchestral grandeur here, seamlessly interpolating Felix Mendelssohn’s “Wedding March” during the track’s dramatic finale.
Listen on Spotify, Apple Music or YouTube
4. Joe Cocker: “The Moon Is a Harsh Mistress”
For this wistful and poetic song, Webb borrowed — with permission — the title of a 1966 science fiction novel by the author Robert A. Heinlein. Despite all its lunar imagery, though, “The Moon Is a Harsh Mistress” captures an experience that is all too human: loving someone who remains impossibly distant. Though it was later recorded by artists including Judy Collins, Linda Ronstadt and Joan Baez, the first to tackle it was Joe Cocker, whose definitive version appears on his hit 1974 album “I Can Stand a Little Rain.”
Listen on Spotify, Apple Music or YouTube
5. Art Garfunkel: “All I Know”
Art Garfunkel chose this soaring and melancholic Webb composition as the first single from his 1973 debut solo album, “Angel Clare.” Backed by the famed session musicians known as the Wrecking Crew, Garfunkel’s ethereal vocals bring an exalted quality to one of Webb’s purest musical declarations of love.
Listen on Spotify, Apple Music or YouTube
6. Glen Campbell: “Galveston”
Though some interpret “Galveston,” Webb’s timeless tale of a homesick soldier, as an antiwar song — especially because Webb wrote it during the conflict in Vietnam — its perspective is actually somewhat ambiguous. The Hawaiian crooner Don Ho was the first to record a version of “Galveston,” in 1968, and he performed it as a mournful if defiant lament: “I’d go home if they would let me / Put down this gun,” he sings. The following year, Campbell had a hit with this more rousing and upbeat countrypolitan take, but he changed that lyric to suggest that the soldier was not fantasizing about shirking his duty: “While I watch the cannons flashing / I clean my gun,” goes Campbell’s version, “and dream of Galveston.”
When Webb released his own recording of “Galveston” in 1972, he certainly leaned into the song’s unease and melancholy. Still, he later clarified that he saw “Galveston” more as a humanist portrait than an unequivocal protest song: “I prefer to say it wasn’t antiwar — that it was more about an individual getting involved in a war and realizing that he’d rather be somewhere else.”
Listen on Spotify, Apple Music or YouTube
7. The Highwaymen: “Highwayman”
Before it became the signature song of the country supergroup the Highwaymen (which featured the real-life outlaw Mount Rushmore of Johnny Cash, Waylon Jennings, Kris Kristofferson and Willie Nelson), Webb released a solo version of “Highwayman” on his 1977 album “El Mirage.” (He wrote its first verse after waking from a nightmare in which he was being chased on horseback.) Campbell played this tale of reincarnation across space and time — the narrator speaks from the beyond in four different voices, as a bandit, a sailor, a construction worker and then an interstellar pilot — for the Highwaymen when they were making their 1985 debut album and suggested they should record it. When the Highwaymen heard the song for the first time, Webb recalls that Cash immediately declared, in his inimitable voice, “Well, I wanna fly the starship.”
Listen on Spotify, Apple Music or YouTube
8. Glen Campbell: “Wichita Lineman”
Perhaps the most celebrated of all Webb’s songs — Bob Dylan once called it “the greatest song ever written”; no big deal — “Wichita Lineman” has been described as “the first existential country song,” for its focus on the internal yearnings of an anonymous workingman. Inspiration for the song came in a flash, as Webb was driving on an unchanging stretch of Oklahoma highway and suddenly whizzed by a lone figure repairing a telephone line. “He was gone very quickly,” Webb once recalled, “and I had another 25 miles of solitude to meditate on this apparition. It was a splendidly vivid, cinematic image that I lifted out of my deep memory while I was writing this song.”
Listen on Spotify, Apple Music or YouTube
9. Frank Sinatra: “Didn’t We”
Early in his career, Webb would sometimes pitch songs to Frank Sinatra, who released a sparse, deeply felt rendition of this elegiac ballad — first recorded by the pop singer James Darren — on his hit 1969 album “My Way.” In his “Great Performances” special, Webb recalls that, when he first played “Didn’t We” for Sinatra, the singer told Webb that the song reminded him of someone from his past. Webb added, “I firmly believe that he recorded it for Ava Gardner.”
Listen on Spotify, Apple Music or YouTube
10. Donna Summer: “MacArthur Park”
It’s a testament to the lightness of Webb’s touch that one of his most ambitious compositions also became one of his most popular: “MacArthur Park,” a multipart suite first recorded by the actor and musician Richard Harris, and later transformed into a disco extravaganza by Donna Summer and the producers Giorgio Moroder and Pete Bellotte. (Summer’s version had a resurgence earlier this year, after the figure skater Alyssa Liu performed a triumphant, gold-medal-winning routine to it at the 2026 Winter Olympics.)
Of all the images in Webb’s songs, the melting cake that someone left out in the rain is perhaps the most memorable, and infamous. It’s an evocative metaphor, but Webb insists it was also a real sight he observed while spending afternoons with an ex-girlfriend in MacArthur Park in downtown Los Angeles. “Everything in the song was visible,” he said. “There’s nothing in it that’s fabricated. The old men playing checkers by the trees, the cake that was left out in the rain, all of the things that are talked about in the song are things I actually saw. And so it’s a kind of musical collage of this whole love affair that kind of went down in MacArthur Park.”
Listen on Spotify, Apple Music or YouTube
11. Jimmy Webb: “P.F. Sloan”
Let’s go out with the rough-hewed voice of Webb himself, and the jewel of “Words and Music,” his 1970 sophomore album. Named and written for a fellow songwriter who encouraged Webb in his early days but later disappeared into obscurity, “P.F. Sloan” is a beautifully rendered reflection on both the elusive craft of songwriting and the fickleness of music industry success. “Don’t sing this song, it belongs to P.F. Sloan,” he sings, with grit, on the chorus. But this one, like so many other classics, belongs to Jimmy Webb.
Listen on Spotify, Apple Music or YouTube
The Amplifier Playlist
“The Sublime Songs of Jimmy Webb” track list Track 1: The 5th Dimension, “Up, Up and Away” Track 2: Glen Campbell, “By the Time I Get to Phoenix” Track 3: The Brooklyn Bridge, “Worst That Could Happen” Track 4: Joe Cocker, “The Moon Is a Harsh Mistress” Track 5: Art Garfunkel, “All I Know” Track 6: Glen Campbell, “Galveston” Track 7: The Highwaymen, “Highwayman” Track 8: Glen Campbell, “Wichita Lineman” Track 9: Frank Sinatra, “Didn’t We” Track 10: Donna Summer, “MacArthur Park” Track 11: Jimmy Webb, “P.F. Sloan”
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