[This article has been updated and expanded in the book Song Book; it originally appeared in Shindig! issue 73]

Hearing that your true love has married someone else is a devastating experience that you wouldn’t wish on your worst enemy. (Unless you are a nasty, miserable excuse for a human being, in which case you should probably be reading a different magazine.)  As music fans, we tend to want our favourite artists to be happy – but we also recognize that an artist’s personal misery often results in great art. And so it is with Jimmy Webb’s ‘The Worst That Could Happen’: a song that draws on Webb’s own life events to brilliantly encapsulate the torment of someone else’s happiness becoming your sadness.

By the time Webb wrote ‘The Worst That Could Happen’ in the mid-60s, he had already been a staff writer for Jobete, Motown Records’ publishing company, and his work had been recorded by the likes of Johnny Rivers and Vikki Carr. But, as he describes in his new autobiography The Cake and the Rain, he was somewhat at loose ends when Rivers asked him to work with The Versatiles, a group managed by Motown executive Marc Gordon.  Webb has recalled being impressed by the group because “there was no sense of ‘band uniform’ like most of the Motown acts had. Here was this black group that had thrown all that away and were dressing very individually. And here was this beautiful sound of a blend of girls’ and boys’ voices. We had five people, so we could do very rich, close harmony, from a more traditional era.”

The Versatiles became The 5^th Dimension, and, after gaining attention in late ’66 with a cover of The Mamas & the Papas’ ‘Go Where You Wanna Go’, they scored a US Top 10 hit in ’67 with Webb’s breezy ‘Up, Up and Away’, from the album of the same name. That success led to arranger Bones Howe asking Webb to work on the group’s next album, The Magic Garden. Howe envisioned the album as “the Jimmy Webb album”, a “song cycle” weaving together Webb’s songs and arrangements.

Webb told Andy Morten of this parish, “There is no denying that The Magic Garden was designed to be cohesive, and though the connections between the songs are not obvious, they were all inspired by the same romantic situation.” That situation was Webb’s on-and-off involvement with his high school girlfriend Suzy Horton. Webb describes her in The Cake and the Rain as “the closest thing I ever had to a childhood sweetheart…She was the quintessential California blonde, with a stunning figure, large blue eyes, and a sweet smile.” Their passionate but turbulent relationship lasted until Horton moved to Nevada to pursue a career as a professional dancer, and met the man who became her first husband. Finding out about their marriage was the event that inspired Webb to write ‘The Worst That Could Happen’.

In his ’98 book Tunesmith: Inside the Art of Songwriting, Webb describes ‘The Worst That Could Happen’ as being structured like a series of connected and increasingly elaborate rooms. “The verse begins a story or chain of reasoning that leads to an expository statement, much like an elegant foyer prepares the visitor for an entrance into a large and impressive room full of architectural detail and significance.” He also depicts the song visually as a sequence of rising waves – to steal a poetic phrase, wave after wave, each mightier than the last. “Songwriters,” he says, “are quite shamelessly playing with the emotions of human beings when we do this and it is a dirty job, but someone has to do it.”

The sweeping crescendos of ‘The Worst That Could Happen’ were ideally suited to a dramatic, powerful vocalist like The 5th Dimension’s Billy Davis Jr. The song was among the group’s favourite tracks on The Magic Garden. However, the potential success of their version was pipped at the post in ’69 when a near-identical rendition by Johnny Maestro and the Brooklyn Bridge reached #3 in the US charts. The 5^th Dimension’s outstanding rendition would have seemed to be an ideal choice as a single from The Magic Garden, but the success of the Brooklyn Bridge’s version likely pre-empted any possibility that The 5^th Dimension’s version could be a hit. However, that didn’t stop Soul City, the group’s record label, from piggybacking on the Brooklyn Bridge’s success; Soul City re-released The Magic Garden in ’69 under the title of, you guessed it, The Worst That Could Happen.

However, one listener – the subject of the song – was not thrilled by its success. ‘The Worst That Could Happen’ was one of “countless” songs that Webb wrote about Horton (the others include ‘Wichita Lineman’, ‘By The Time I Get to Phoenix’, and ‘MacArthur Park’). Webb admits in The Cake and the Rain that Horton was bothered by his ongoing musical declarations of unrequited love, which were “a devastating and constant psychological weapon on the radio.”

‘The Worst That Could Happen’ was covered several times, in ’69 and later, by a variety of acts including the Lettermen, BJ Thomas, and J. Vincent Edwards. It also regularly showed up on records by groups like the Johnny Mann Singers, who specialized in softening popular songs into “easy listening”. Even the more musically adventurous acts that covered the song, like Tinkerbells Fairydust and The Goodees, kept their interpretations fairly close to Webb’s original arrangement. The most different version, surprisingly, may be Webb’s own rendition from ‘96’s Ten Easy Pieces, on which he performed songs he had written that had been hits for other artists. Webb is definitely not a shouter when he sings, so his rendition of ‘The Worst That Could Happen’ is an intimate, low-key affair foregrounded by just his voice and piano. Not surprisingly, given his personal affinity with the song, the toned-down arrangement works remarkably well even without the usual dramatic vocalizing.

Webb reveals in The Cake and the Rain that Horton’s mother regularly notified him when Horton was encountering difficulties in that first marriage. When she and her husband eventually separated, he seized the opportunity to rekindle the flame. They became a couple again in the early ‘70s, but Webb’s philandering and drug use drove them apart. Horton developed a musical career of her own, married Linda Ronstadt’s cousin Bobby, and now performs with him and former Stone Poneys member Bobby Kimmel in the group I Hear Voices!.

In addition to working as a solo artist, Webb has explored writing for musical theatre and for orchestras, as well as overseeing the legacy of his vast musical catalogue. In May of this year, his work was recognized in a “Celebration of Jimmy Webb” concert at Carnegie Hall. The event was staged as a fundraiser for research into Alzheimer’s disease, the terrible condition that in August claimed Webb’s “brother in music” Glen Campbell. One of the highlights of the show was Billy Davis Jr.’s soaring rendition of ‘The Worst That Could Happen’.

And while romantic anguish inspired ‘The Worst That Could Happen’, the story of the relationship behind the song actually has – well, not a traditional happy fairytale ending, but a resolution in a connection of mutual respect and affection. “Jimmy’s songs have followed me my whole life,” Horton told the Los Angeles Times in 2013, “and we are still friends to this day. Jimmy has a lovely wife and I have a wonderful husband. They have both had to deal with our histories. I mean no disrespect to anyone but I have to say, I have loved Jimmy for 50 years and I always will.”