[This article has been updated and expanded in the book Song Book; it originally appeared in Shindig! issue #59]

‘The First Cut Is The Deepest’ has been a hit for several artists in several countries over several decades, but’s it a challenging song to unravel. A deceptively simple ode to resignation and redemption, its composer Cat Stevens has said “The words of my songs speak for themselves”, and many of the artists who have covered the song don’t appear to have much to say about it either. But ‘The First Cut Is The Deepest’ has often marked a time of transition in its performers’ careers – which perhaps is fitting for a song about moving into a new relationship while dealing with the emotional baggage of a previous relationship.

The former Steven Georgiou may have recorded a demo of ‘First Cut’ as early as ’65, and it was likely among the dozen or so songs that Stevens played in his ’66 audition for producer Mike Hurst. Growing up in the intellectual and cultural melting pot of London’s West End, and absorbing an eclectic range of musical influences from Bob Dylan to the Beatles to Broadway musicals, Stevens had a fresh, distinctive approach to songwriting. He quickly found success in ’66 with the singles ‘I Love My Dog’ and ‘Matthew and Son’, and then found that success created the expectation of more success.  But, he told interviewer Michael Wale, “it’s not as easy as that because the songs aren’t like that. Life isn’t like that, you just don’t do the same thing over and over again. You do it another way, somewhere else.”

In early ‘67, Hurst was working with vocalist PP Arnold, who had been signed to Andrew Loog Oldham’s Immediate label. After Arnold’s first single flopped, Hurst sought new material for her. Stevens “had this song and it wasn’t finished, but the idea was there, the title and everything and the basic tune. Pat [PP] needed a song, so I played a few things and we just finished this one. It really suited her, but I can’t say I wrote it for her because I can’t do that sort of thing.” Allegedly, Stevens received a mere £30 for letting Arnold record the song. Her stormingly soulful rendition, released in May ’67, reached #18 on the UK charts.

In October ‘67, Stevens recorded ‘The First Cut Is the Deepest’ himself, for his second album New Masters which was released in December. By that time, the relationship between Stevens and Hurst had deteriorated to the point where, according to Hurst, “[w]e did the album with lawyers actually in the studio. It was horrendous.” When asked to compare his take on the song to Arnold’s, Stevens said, “I didn’t like my version too much. I preferred hers.” In mid-’68, a bout with tuberculosis, exacerbated by stress and overwork, put Stevens in the hospital for several months. During that time, he rethought his musical direction, and re-emerged as the bearded troubadour who became an international star with albums such as Mona Bone Jakon and Tea for the Tillerman.

‘First Cut’ also made a detour to Jamaica in ’67. Sir Coxsone Dodd, at his renowed Studio One, produced Norma Fraser’s reggae version of the song, which was released in October on a double single with Bumps Oakley’s ‘Rag Doll’. In ’68 in the UK the Koobas took the song in another direction with their fuzztone- and echo-drenched interpretation, laced with searing guitar solos.

As a DJ on Radio Caroline, Keith Hampshire likely would have been familiar with both Arnold’s and Stevens’ ‘First Cut’. During his stint at the pirate radio station, Hampshire released a novelty single under the name of ‘Keefers’, but it was only after he returned to his native Canada that he seriously pursued a recording career. Produced by Bill Misener, a former member of Toronto psych legends The Paupers, Hampshire’s ’73 rendition of ‘First Cut’ was a #1 hit in Canada and made the Top 10 in Australia. Its horn-powered arrangement evokes the sound of other popular bands of the time, such as Lighthouse and Blood, Sweat and Tears – and indeed, more than a few commentators noted the vocal similarities between Hampshire and BST’s David Clayton-Thomas.

Dozens of covers of the song followed in subsequent years, including numerous reggae interpretations by such well-known acts as Marcia Griffiths, Judy Mowatt, Dawn Penn, and I-Roy. But many of the non-reggae versions, unfortunately, demonstrated how hard it is to perform this song well. ‘First Cut’ has a gorgeous melody and chord progression – brought out in Martin Simpson’s charming slide-guitar instrumental interpretation – but to truly capture its lyrical dimensions, a singer must convey vulnerability, world-weariness, and determination. The two versions of ‘First Cut’ that were most successful in the US are examples of when this is and isn’t accomplished.

Rod Stewart recorded ‘First Cut’ during the sessions for his ’75 album Atlantic Crossing, which marked his move to the US, but the song didn’t appear until his ’76 album A Night on the Town. The appalling ‘Tonight’s the Night’ was the first single from that uneven album, but ‘First Cut’ was roundly praised by reviewers. Bud Scoppa in Phonograph Record noted, “[It] has all the poignance and passion of the mature Rod Stewart. When he hits the chorus — ‘When it comes to being lucky she’s cursed/ When it comes to loving me she’s worse’ — there’s no doubt that Stewart owns those lines absolutely.” ‘First Cut’ eventually became the third single from A Night on the Town. Released in ’77, it reached #19 in the US and #1 in the UK, where, in a temporary victory for spandex and eyeliner, it kept the Sex Pistols’ ‘God Save The Queen’ from topping the singles charts.

Sheryl Crow’s 2003 interpretation of ‘First Cut’ was initially a bolt-on for her greatest-hits set The Very Best of Sheryl Crow, but it received enough airplay that it was released as a single. Crow is an enormously accomplished musician who often doesn’t get the credit she deserves for the quality of her work, but her take on ‘First Cut’ is overly glossy and emotionally monotone. Nevertheless, it became a crossover hit by reaching both #14 in the US pop charts and #35 in the US country charts, and thus paved the way for her current career as a country artist.

In ’77, after a near-death experience, Stevens became a Muslim and changed his name to Yusuf Islam. He abandoned his musical career and, according to several reports, went through his song catalogue to identify songs he deemed as being “anti-God” and which he then disassociated himself from. It’s not clear whether ‘First Cut’ was ever on that list, but when Yusuf returned to live performing in the early 2000s, ‘First Cut’ was part of his shows, and it remains in his set list to this day. In 2006, Yusuf received the award of ASCAP Songwriter of the Year, with ‘First Cut’ being cited as an “enduring classic”; it’s also mentioned as a “modern standard” in his biography at the Rock and Roll Hall of Fame, which he was inducted into in 2014.  After 50 years, the words of ‘First Cut’ are still speaking for themselves.