Perhaps it could only happen to a white American boy writing songs and recording music during the first decade of rock ’n’ roll and at a time of American economic and cultural supremacy that, at his death on 3 February 1959, at the age of 22 years and 149 days, he could leave behind such a wealth of recorded material and a life of such tragic and tangled consequence.

Buddy Holly was born in Lubbock, Texas, in 1936 and came to prominence at the tail-end of the first wave of rock originators: Presley, Little Richard, Jerry Lee Lewis and Gene Vincent. Having left Texas and his band of the previous years, The Crickets, Holly set off from New York for his final tour and the plane crash that would take his life. His home was a modern apartment at 11 Fifth Avenue in Greenwich Village, and it was here on a portable Ampex tape recorder that Holly was to make his last set of recordings. They are known as the ‘apartment tapes’ and contain new songs, sketches and cover versions, and they sound very different from Holly’s official recordings; the latest of which was the orchestra- and string-led sessions for ‘True Love Ways’ and ‘It Doesn’t Matter Anymore’. Amidst these freshly written songs was a number called ‘Peggy Sue Got Married’. It begins with the opening chords of ‘Peggy Sue’ and then shifts to a new melody whilst rhythmically and stylistically echoing the earlier hit. Musically it is playful, and artistically it is a fresh idea – linking songs from varying career stages into a continuing narrative – and it is also of note that Holly was married when writing the latter song but single when composing ‘Peggy Sue’. Like other late-period, self-penned classics on the tape, such as ‘Crying, Waiting, Hoping’ and ‘Learning the Game’, ‘Peggy Sue Got Married’ gets a breezy, confident performance from Holly on acoustic guitar and vocal.

Fifty-three years later the song leaps from the New York apartment to a full band recording in South Pasadena, California. John Doe is singing. He is from the LA punk-era band X, and his voice has the craggy, ‘seen and done it all’ tone of Mark Lanegan or Tex Perkins. The band is ragged as the singer and the song is pushed to almost four minutes from Holly’s one minute, 46 seconds. This is an act of wilful and purposeful transformation, no mere cover version, but taking the cheekily sung facts of the original and pumping it up with a magnificent arrangement to big, heartbreaking news of the marriage of a former lover or friend. Four songs earlier on Rave On Buddy Holly, a 19-track compilation of artists performing the songs of Buddy Holly, Modest Mouse have taken the opening lines of ‘That’ll Be the Day’ at face value – “That’ll be the day when you say goodbye / That’ll be the day when you make me cry / You say you’re going to leave me, you know it’s a lie” – to turn a rocking pop song into a burnt-out piece of Americana and, like Doe, they have injected their interpretation with a fevered new meaning that also honours the emotion of the original. No other artists on the record will be so bold, or so successful, settling instead for varying degrees of reverence in interpreting the Holly originals.

Rave On is released to mark the seventy-fifth anniversary of Holly’s birth and it is a testament to his stature that such a tribute has been instigated, with so strong a collection of contributing artists. Paul McCartney, Lou Reed and Graham Nash are the old guard, starstruck teenagers no doubt during Holly’s blaze of back-to-back hits. Patti Smith and Nick Lowe represent the next tier in age and career, leaving the bulk of the album to younger, mostly American artists, sympathetic to the project through musical outlook. A Holly record without Holly the performer serves to heighten the emphasis on his songwriting and he is, with Chuck Berry and Hank Williams, one of the three great singer–songwriters of the 1950s. Each of them was a significant influence on the evolution of rock in particular and songwriting in general over the succeeding decades; Holly’s hand was particularly felt in the ’60s, when his electric, rhythm-guitar pop sound and hooky songs affected a generation of rock bands, none more than The Beatles, who performed his songs and whose first-ever recording, as The Quarrymen, was a cover of ‘That’ll Be the Day’ – done when Holly was still alive.

An album of 19 tracks by various artists is never going to have the flow of a normal record – as a listening experience, it’s stop and start. With the performers having recorded in isolation, those who commissioned them hope in the accumulation of tracks to present a portrait, or at the very least a contemporary response to Holly’s legacy. What does get exposed is the methods that most artists use when covering another person’s song. The process begins with song selection and then moves to instrumentation and arrangement. Holly being a ’50s artist means there is going to be a lot of rockabilly guitar and reverb-ed vocals. Justin Townes Earle on ‘Maybe Baby’, Nick Lowe on ‘Changing All Those Changes’ and Jenny O with ‘I’m Gonna Love You Too’ echo the originals and attain only accuracy, while Gnarls Barkley’s Cee Lo Green on ‘(You’re So Square) Baby I Don’t Care’ and Kid Rock on ‘Well All Right’ give their tracks an Amy Winehouse–like retro shake and bring them to life. Sometimes a great cover version can stick close to the original, and imbuing it with a certain spirit or the lick of a great talent can transform a song without major change. A wonderful example of this is Fiona Apple and Jon Brion’s take on ‘Everyday’ – the chiming celeste is there, the light three-chord strum; doing the song as a duet and Apple’s smokey voice earn it a place alongside Holly. Similarly, The Black Keys pick an ‘apartment tape’ obscurity, Mickey and Sylvia’s ‘Dearest’ and, with inventive care, augment it with a great vocal from the band’s Dan Auerbach.

The second half of the album is better than the first; the more adventurous and older artists are here, including John Doe and Modest Mouse. The record is blunted by an earlier run of younger artists (She & Him, Karen Elson, The Strokes’s Julian Casablancas) who, though enthusiastic, contribute little more than a sonic update to what Holly and his band did 50 years before. They have inexperience and, perhaps, a sense of awe as mitigating factors, but no such excuses exist for Paul McCartney. He comes in at song three with an overheated, stadium-rock take on ‘It’s So Easy’ that also contains two rap or scat sections, where McCartney (presumably with his band not knowing where to look) goes into a preacher-man – “we’re gonna be down by the old juke joint” – routine. A cough into the talkback mike from The Beatles’ producer George Martin or a narky put-down by John Lennon (a Holly worshipper) would have had this in the bin, but who’s telling McCartney now? Lou Reed does better with ‘Peggy Sue’ (nicely sequenced before ‘Peggy Sue Got Married’), his voice not too far from scary pensioner, as he kind of gets the melody over a wild, art-rock backing (including Laurie Anderson gamely wailing away on electric violin). A decent mix may have had this as a late-period Reed masterpiece.

Which leaves Graham Nash and Patti Smith. Unlikely bedfellows – Nash the genial west-coast hippie, Smith the fire-tongued New York poet. Both, though, know how to sing a song that moves them and both are enamoured of Holly. Nash used to be in The Hollies, a band named after its musical hero. He ends the album with a heartbreaking version of ‘Raining in My Heart’. The arrangement idea may be simple – strip the song of its original violins and sugar production and go earthy with Fender Rhodes and a straight vocal – but gee it works. And Patti Smith continues a late-career purple patch. Her recent memoir Just Kids is the best thing she has ever done, and although her career has seen cover versions as one of the planks of her recorded work, there is a confidence and gravitas to her voice when she starts to coo the lyrics to one of Holly’s finest songs, ‘Words of Love’, that puts most of the singing on Rave On in the shade. And if you listen intently, you can hear a few words of Spanish. Why? At a guess she is addressing the Puerto Rican–born María Elena Santiago, Holly’s surviving widow, who could be heard washing dishes and talking on the ‘apartment tapes’ all those years ago.

There is much speculation about what Holly would have done musically had he lived longer, and there can be no doubt that part of the romance of the man, and the fascination that he still holds, comes from his early death. Like James Dean, he artistically never made a foolish move. What would he have done? Some argue and project from the pop productions of his last records and the folk style and Greenwich Village wanderings of his last months, and have him leading both The Beatles and Bob Dylan into the ’60s. Footage of him on English TV in 1958 has him rockin’ in style but with a severely receding hairline for a 21 year old. It might sound a ridiculous point to add to the debate, but a balding Holly in his late twenties when mop-top beat groups and then psychedelic rock are hitting? Rave On has him as a master tunesmith – maybe he would have stayed at home and written some more glorious songs.

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