I was a highwayman

Along the coach roads I did ride

With sword and pistol by my side

Many a young maid lost her baubles to my trade

Many a soldier shed his lifeblood on my blade

The bastards hung me in the spring of ‘25

But I am still alive

 

Jimmy Webb’s songs boom through the pantheon of great American music, echoing humanity’s deepest, most universal feelings – longing, heartbreak, grief. His words border the plane of existence – the lived reality of America’s blue-collar, its outlaws, its forgotten soldiers – and a collective subconscious, where dreams of reincarnation twirl into an eternal nightmare – the inevitable fear of death lingering at the end of a long, dark highway. His music captures what is fleeting, unravels what is confined, finds beauty in what is broken and finds sorrow where there was once joy.

 

MacArthur’s Park is melting in the dark

All the sweet green icing flowing down

Someone left the cake out in the rain

I don’t think that I can take it

‘Cause it took so long to bake it

And I’ll never have that recipe again

Oh, no

 

He’s revered as one of the greatest songwriters to ever live, balancing complex, jazz-inspired chord structures and experimental arrangements with stories about ordinary people that have resonated with audiences for decades. Bob Dylan once called his lonely western ballad “Wichita Lineman” the greatest song ever written.

 

I am a lineman for the county

And I drive the main roads

Searchin’ in the sun

For another overload

I hear you singin’ in the wires

I can hear you through the whine

And the Wichita lineman

Is still on the line

 

But before he was penning hits for Frank Sinatra, Donna Summer, Glen Campbell, Judy Collins, Willie Nelson, Kris Kristofferson, Waylon Jennings and Johnny Cash, Jimmy Webb was a “kid from the farm,” arriving from rural America to Southern California as a teenager in the 1960s. In an interview, he described moving to Los Angeles as “revolutionary.”

“The Beach Boys were wafting from every window, from every car radio,” said Webb, who now lives in Long Island. “It was really a great, eye opening introduction to Southern California.”

Webb was born in Elk City, Oklahoma, a small town along historic Route 66, and grew up about 100 miles north, in the rural community of Laverne. As the son of a Baptist minister, Webb’s childhood was shaped by religious fundamentalism and physical labor.

“I had a driver’s license when I was 15 years old because we got out of school to harvest, and we had to drive,” he said.

Some of his earliest musical memories in Oklahoma are of hearing a young Glen Campbell over a plastic transistor radio – an artist he fatefully vowed to one day write for.

Just like the Mother Road, Webb would go west. After his father accepted a role as a pastor in San Bernardino, the family moved to the Inland Empire, where Webb was exposed to L.A.’s burgeoning pop music scene, and his world opened up for the first time.

“This was like discovering heaven for me, because I was raised in a non-dancing family. That was one of the rules of our religion, was that dancing would lead to evil things,” Webb said. “All of a sudden, I could play in a band, the rules were relaxed a little bit.”

The 1960s saw a tidal wave of music come to life in Southern California – Dick Dale and the frenzy of “beach craze” musicians, crooning pop acts like the Righteous Brothers, the Beach Boys and their transformative “Pet Sounds” record. As Webb absorbed the sonic world around him, he befriended local DJs and musicians – Jimmy Messina, half of Loggins and Messina, was in the class ahead of him at Colton High School – and a new era of songwriting began to take shape.

“I was an unfinished product when I arrived in California. And when I left California, I was sort of a different person,” he said.

He began his career transcribing music for a publishing agency in Hollywood. By the time he was 19, he was under contract with Motown Records as a songwriter, working out of Chaplin Studios on La Brea Avenue and Sunset Boulevard.

“I owe everything to California,” Webb said. “California has been very good to me. I love it, and I miss it sometimes. In my mind, I still know every street, I know every corner.”

California’s influence extended far beyond the records Webb heard on the radio. In sun-soaked ‘60s Los Angeles, he found himself surrounded by a generation of songwriters who challenged his understanding of what popular music could be. He spent time with musicians including Gerry Beckley and Dewey Bunnell of America, Harry Nilsson, Johnny Rivers and Joni Mitchell, gathering at places like the Hollywood Roosevelt Hotel, Lucy’s El Adobe on Melrose Avenue and the Cock ‘n Bull on the Sunset Strip.

Of the artists he encountered in Los Angeles, Webb said Mitchell had perhaps the greatest influence on his own writing.

“I changed my whole style of writing when I met Joni,” Webb said. “Joni Mitchell told fabulous stories. She opened a new book for us of what she would reveal about herself. She, along with Randy Newman, is one of the people who kind of invented conversational tone – which is lyrics that are not really flowery. They just sound like people talking to each other.”

The people, places and stories of Southern California all had a profound impact on Webb as he began writing many of his most iconic songs.

“It was just a comprehensive, 360-degree education, re-education of me as a human being, I can’t over emphasize that,” Webb said. “And I loved it.”

In the late ‘60s, after scoring his first major hit with “Up, Up and Away” – a shimmering pop tune that was recorded by The 5th Dimension and swept six categories at the Grammys – Webb moved into a home on Kirkwood Drive in Laurel Canyon, the epicenter of the hippie movement in Southern California. As the counterculture rejected the material, embraced the abstract and sought new ways of connecting with a spiritual realm, Webb’s creativity broke free.

“I had one piece of furniture,” Webb said. “I had a grand piano that I bought with the royalties from ‘Up, Up and Away,’ and I slept under the piano – a nine foot concert grand. It’s like the Titanic. I slept under it, and I would just get up and sit down on the bench and start writing. I would write three, four songs a week. I was pouring them out.”

It was underneath the grand piano nestled in Laurel Canyon in 1967 where Webb would write his seven-minute orchestral epic “MacArthur Park,” a nod to the Los Angeles locale where Webb would frequently meet his then-muse Suzy Horton.

Webb offered the song to the sunshine pop group The Association, who rejected it because it would not fit on their album due to its unusual length. However, the song was brought to life when it was recorded by Richard Harris, an Irish actor who had never laid down a record.

The Harris rendition became an unexpected hit on underground radio stations that played longer, jam-band recordings by acts like the Grateful Dead that were being passed by the major rock ‘n’ roll stations. “MacArthur Park,” despite its unheard-of 7 minute and 21 second runtime, eventually forced its way onto top 40 radio, even prompting stations to rearrange their ad sequences.

“The DJs loved it,” Webb said. “I’ve had DJs tell me they’d go home and feed their dog during ‘MacArthur Park.’ I’ve heard them tell me they did other things, which I don’t think you want to print. They did all sorts of things while ‘MacArthur Park’ was playing – it was like a coffee break for them.”

Throughout the next few years, artists across various genres would deliver their own unique renditions of the surreal pop song – Waylon Jennings, Tony Bennett, the Four Tops and Maynard Ferguson, to name a few. In 1978, “MacArthur Park” was reincarnated yet again, with a disco version by Donna Summer smashing the charts.

“I remember the day that Donna’s record went No. 1, and I hired a limousine and I just drove around all day saying to myself, ‘I’m number one, I’m number one, I’m number one,’” Webb laughed. “I would roll down the window and tell people on the sidewalk, ‘I’m number one.’ It was just a big deal for me.”

The song has experienced a level of immortality that few compositions enjoy, with pop culture appearances including a reference to the lyrics in “Seinfeld,” a brief sample in rapper Kendrick Lamar’s 2024 single “TV Off” and even as a soundtrack in a 2026 gold medal-winning Olympic performance by U.S. figure skater Alysa Liu.

With more than 60 years of material, Webb’s music continues to live on in America’s collective consciousness, and he is currently working on a new album with songs that were previously written but never recorded.

“I think it’s going to be very interesting for people to hear some of the songs that were overlooked,” Webb said. “It’s going to be called, ‘Yours for the Taking: Found Music.’”

In the long road of Webb’s career, perhaps no song has taken on a life of its own quite like “Highwayman.” The haunting tale of rebirth emerged out of Webb’s subconscious – a nightmare that shook him awake while he was in London in the mid-1970s.

“It started out as a very vivid dream that I woke up from. Night sweats. I was terrified – to be chased and to think that I was going to be hung from a tree. It was very real,” Webb said. “I rolled out of bed. I always kept the piano close to my bed, even when I was on the road. I still do if I can. I rolled out of bed and jumped on the piano and wrote the first verse … It had this otherworldly, sort of supernatural aura of a guy changing bodies but retaining his consciousness, living different lives, but never forgetting who he was.”

Webb took the song back to California, where he showed it to Glen Campbell, who immediately fell in love with the ethereal composition.

“Glen took it over to Capitol Records. He said he wanted to do it. They didn’t want him to do it. He quit Capitol,” Webb said. “He quit them after 12 years. They wanted him to cut ‘My Sharona.’ So he stormed out of there.”

Years later, in 1985, producer Chips Moman had assembled the Four Horsemen of outlaw country music – Willie Nelson, Kris Kristofferson, Waylon Jennings and Johnny Cash – to cut a record with the help of Campbell, who taught the supergroup “Highwayman.”

Webb recalled that Johnny Cash was the last to hear the song, and the rest of the group was concerned that as a devout evangelical Christian, the theme of reincarnation might not sit well with “The Man In Black.”

“They were all on pins and needles waiting to see what ‘Big John’ would say about it,” Webb said. “They played my demo, and after my demo was over, they all sat there waiting for John, and finally John looked up and said, ‘well, I want to fly the starship.’”

The supergroup scored a No. 1 country hit with Webb’s song, even deciding to name themselves “The Highwaymen.”

Decades later, “Highwayman” remains one of Webb’s enduring works – a meditation on time, consciousness and mortality.

 

I’ll fly a starship

Across the universe divide

And when I reach the other side

I’ll find a place to rest my spirit if I can

Perhaps I may become a highwayman again

Or I may simply be a single drop of rain

But I will remain

And I’ll be back again

And again and again and again and again and again and again