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(Credit: Brunswick Records)


Six definitive songs: The ultimate beginner's guide to Buddy Holly


If you’re to believe the news, the genre of rock music is officially dead. While we’d bet the band of the moment would wholly disagree, we still feel it’s our duty to deliver you some lessons in rock’s greatest artist. Up for our brief introduction, today is Buddy Holly.

As we aim to offer up a little insight into the rock icons of the 20th century, we’re distilling their back catalogues into just six of their most defining songs. The tracks that offer up the first steps in getting to know the music and the person behind the legend.

When you’re thinking of rock ‘n’ roll legends it’s hard to find an artist more integral and pivotal in the genre’s birth and cultivation than Buddy Holly. Born in Texas on September 7th 1936, much of Holly’s legend is sadly swallowed up by his famous death, a moment in history known widely as “the day the music died”.

Involved in a plane crash alongside Ritchie Valens and The Big Bopper, Holly sadly died at the height of his fame. He was only 22 but despite his young age had begun to find nationwide acclaim and beyond. As the new generation of rock ‘n’ roll came to the fore, pushing pop music as it did, Holly was an integral member of the welcoming party.

After a run of supporting both Elvis Presley and Bill Haley, Holly decided that music was the only career for him and with the help of Eddie Crandall was signed up to Decca records. Disappointed with the results of being with a major, Holly took himself to see Norman Petty and form The Crickets. It was at Petty’s studio and with Brunswick Records that some of his most cherished songs were composed and recorded.

Holly toured the world following a string of successful songs but his opportunity to become the leading light of pop music in the new decade was cut short when he perished in that fatal aeroplane crash. Below, we’re providing you with the ultimate beginner’s guide to Buddy Holly and bringing you his six definitive songs.

Buddy Holly’s six definitive songs:

‘That’ll Be The Day’

Arguably Holly’s most widely adored creation, ‘That’ll Be The Day’ was written alongside Jerry Allison and performed with both the Three Tunes in 1956 and with The Crickets a year later in 1957.

The song is about the audio equivalent of a warm cup of coffee. Though it’s hard, looking back from 2020, to not see the song bathed in a golden-hued glow of nostalgia, the track also has a punch of energy and the unstoppable push of caffeinated teenage romance. The song was a noted inspiration for The Beatles and even covered by The Quarrymen in their time. It’s a joy even six decades later.

‘Peggy Sue’

The target of Holly’s affections on ‘Peggy Sue’ was Peggy Sue Gerron, the then-girlfriend of Holly’s drummer Jerry Allison. Allison, who wrote the song with Norman Petty, and Peggy Sue were dating when Holly wrote the song and the pair later married before divorcing a little over ten years later.

While the characters in the song may not have got their happy ending, the song has gone down as an esteemed part of pop music history. In Gerron’s memoir, Whatever Happened to Peggy Sue?, she stated that she first heard the song at a live performance at the Sacramento Memorial Auditorium in 1957 and that she was “so embarrassed, I could have died.” We’d quite like such a historic song named after us.

‘Oh, Boy!’

Originally recorded by Sonny West in the late fifties, the song failed to achieve any real success until The Crickets picked up the track for their own rocking rendition. The track was released backed with ‘Not Fade Away’ as the B-side and hit the charts in early 1958.

On the BBC’s Classic Albums series in 2019, West said, “I had a decision to make whether to say I want to do it myself and I said ‘No, I want Buddy to do it’, it can’t hurt anything and if it didn’t work I could go back and do it myself someday.”

In the same programme, West said of the lyric changes Holly made, “I said ‘All my love, all my kissing, you’re gonna see what you’ve been missing’. And with Buddy’s verse, ‘All my love, all my kissing, you don’t know what you’ve been missing’. I have no idea, maybe it has more punch that way.” Whichever way you cut it, ‘Oh! Boy’ is a powerhouse rock number.

‘Not Fade Away’

It’s not often that B-sides become behemoths in their own right but this 1957 song recorded with Holly and The Crickets is a juggernaut fo a rock ‘n’ roll song. Though it may not have received the credit it was due upon its first release, once The Rolling Stones got a hold of it, the track shot into stardom.

Many have pointed to this being the final song that Buddy Holly played before his untimely death. But this myth was perpetuated by the biopic The Buddy Holly Story which came out in 1978 and was purely poetic license. No matter, the song still remains one of Holly’s undying contributions to the rhythm of rock.

‘Rave On’

‘Rave On’ was originally written by Sonny West, Bill Tilghman and Norman Petty. Petty wanted to give it to another act, but Holly protested and persuaded the songwriters to let him record it—after West had already had a turn, of course. The song was recorded later that year and has become a key part of Holly’s iconography.

It was one of six recordings to hit the charts that year and signified that Holly’s career was beginning to really take off. Like many of Holly’s songs, and acting as a key indicator of his huge influence on the genre, this one has been covered by a host of huge names, everyone from John Mellencamp to Julian Casablancas have had a go.


Acting as a precursor to the pop ditties that would make the British Invasion bands land on American soil with the bit between their teeth, Holly’s delicate vocal and all-round tenderness on this song has made it a favourite with filmmakers and directors alike. It has featured in countless films and it is easy to see why.

The song is perfectly imbued with the innocence of a by-gone age and a gentle optimism that is hard to dislike. Written by Holly and Petty and released in 1957, the song has transcended genre and style and found its way into the setlist of many big performers including Fiona Apple, Erasure, James Taylor and more.