Essentials: The Top Ten Buddy Holly Americana Covers

It is a testament to his lasting influence and the fact that his songs have entered mainstream culture that Charles Hardin Holley, also known as Buddy Holly, is still a pervading musical presence 65 years after his tragic death in a plane crash in Clear Water, Iowa on 3^rd February 1959. This is even more remarkable when you consider the fact that his breakthrough hit ‘That’ll Be The Day’ was released in July 1957, and he only released three albums during his short career. While Elvis clearly influenced the British groups of the British Invasion, it was Holly who showed them the way as a guitar-playing singer-songwriter. His influence is also clear on the new wave artists of the late ‘70s and early ‘80s and beyond. However, he was never as popular in America as he was in the UK, and his last influence in his home country has been on more roots-orientated artists.

Buddy Holly was born in Lubbock, Texas, during the Great Depression on September 7^th, 1936 and grew up listening to the music of the day which included Bill Monroe, Bob Wills, Hank Williams and Hank Snow, and started playing country music before seeing Elvis Presley perform. While country music was his biggest influence, his guitar playing was influenced by artists such as Django Reinhardt, Chuck Berry, and Les Paul. While the backing band The Crickets are synonymous with him, they only became a named band because of contractual complications, and Holly changed the members of the band and recorded solo sides during his career.

It may surprise some listeners that some of his better-known songs were actually released posthumously during the ‘60s. His original backing band from Lubbock carved a career for themselves in the ‘60s with various musicians joining Jerry Allison and Sonny Curtis and playing sessions on America’s West Coast. Buddy Holly’s legacy got a boost in 1970 when fan Delaney Bramlett produced the Crickets’ “Rockin’ ‘50s Rock’n’Roll” which included new versions of Buddy Holly’s songs at what was the start of the first rock & roll revival. This provided the impetus for the Crickets to record and tour again, and this time they were joined by British musicians Ric Gretch on bass and Albert Lee on guitar, who originally was simply filling in for keyboard player Glen D. Hardin. A singer-songwriter friend of Grech expressed an interest in joining the band, but as they were taking a tour of the American South to Nashville to record, Sonny Curtis thought the new guy’s known drug use would be a problem. That singer-songwriter was none other than Gram Parsons.

From the ‘70s Buddy Holly’s music, and particularly his songs, have achieved iconic status, and have proved popular with roots and Americana artists through the subsequent decades.  In this list, I’ve attempted to show the broad influence Holly’s music has had on Americana, and also tried to give a representative sample of his songwriting skills which has proved a challenge with only ten songs to play with. Whatever readers think of the selections, and as always views and comments are encouraged, I am sure the music certainly didn’t die that day in Clear Lake, Iowa in 1959.

Number 10: Linda Ronstadt ‘That’ll Be The Day’  (1977)

Linda Ronstadt released her version of ‘That’ll Be The Day’ twenty years after Holly achieved his breakthrough success with it in 1957. Holly wrote the song in 1956 with Jerry Allison after watching The Searchers with John Wayne where he used the phrase a lot. The first version of the song was recorded in Nashville in 1956 with Sonny Curtis, Jerry Allison, and Don Guess, but it was not released at the time. Holly re-recorded the single version of the song in Clovis, New Mexico, in 1957 under the direction of Norman Petty, who got a co-write, with Joe B. Maudlin and Jerry Allison. The single was released under the name of The Crickets on Brunswick due to Buddy Holly still being under contract to Decca at the time, and was included on The Crickets’ first album, “The Chirping Crickets”.

Linda Ronstadt’s version was included on 1976’s “Hasten Down The Wind” and was a major success when released as a single. Other songs on the album were written by Willie Nelson, and then emerging songwriters Karla Bonoff and Warren Zevon, which emphasised the quality of the songwriting of ‘That’ll Be The Day’.

Number 9: Danny Gatton (with Rodney Crowell) ‘It Doesn’t Matter Anymore’  (1993)

Danny Gatton was a one-of-a-kind guitar player who didn’t really like touring which helps explain why he wasn’t more widely known and appreciated before his tragic death in 1994 from a self-inflicted gunshot wound. With his fifties quiff, he was often classed as a rockabilly guitarist, something his association with Robert Gordon reinforced. He himself called his music redneck jazz to better reflect his wide range of influences that included Les Paul, Charlie Christian, Scotty Moore, and Chet Atkins. He was given the nickname The Humbler because of his ability to beat other guitarists in cutting contest jam sessions.

By the late ‘80s he’d made enough of a reputation that he was offered a 7-album deal with Elektra Records, and he got a Grammy Nomination for ‘Elmira Street Boogie’ from his debut Elektra record, “Elmira Street” in 1991. Changes in Elektra, and lack of sales due to his eclectic mix of genres, meant that his second album, 1993’s “Cruisin’ Deuces” was his last album for the label. “Cruisin’ Deuces” upped the country content and added a couple of guest vocalists, Gatton may have been a fantastic guitarist but he wasn’t a vocalist which may also have limited his commercial appeal.

In 1958 Buddy Holly was beginning to spread his musical wings, expressing an interest in recording with Ray Charles and Mahalia Jackson. He recorded four songs in late 1958 in New York backed by an 18-piece orchestra which included jazz saxophonist Boomie Richman. One of the songs recorded was Paul Anka’s ‘It Doesn’t Matter Anymore’ which was the last single released in his lifetime, and had been specifically written for him. Danny Gatton’s version includes the usual mix of genres but keeps things rooted in the Texas dirt with the addition of Rodney Crowell on vocals who brings his own take on the Holly trademark hiccup to the recording.

Number 8: Marshall Crenshaw ‘Crying, Waiting, Hoping’  (1987)

Nineteen eighty-seven was a major year for roots rock royalty, Los Lobos. They were able to put their head above the commercial parapet for a while and had a million-selling album and single. The challenge proved to be the fact that their success was due to their participation in the soundtrack to the biopic of Chicano teenage artist Richie Valens, who died in the same plane crash as Buddy Holly. The film “La Bamba” and its soundtrack were not only a commercial success, but also an artistic success and the film was added to the National Film Registry of the Library of Congress in 2017.

While Los Lobos played eight of the twelve songs on the soundtrack, Marshall Crenshaw covered Holly’s ‘Crying, Waiting, Hoping’. Crenshaw had been unsure when he was offered the part of Buddy Holly in the film but was won over by the quality of the screenplay. Also, while Holly was clearly an influence, his own songwriting was showing that he was his own man and who was not going to be constrained by expectations or genres. E Street Band bassist Gary Tallent was just beginning to spread his wings as a studio musician and producer when he produced ‘Crying, Waiting, Hoping’ after suggesting the song to Crenshaw. In the 1990s Tallent moved to Nashville and worked with artists like Jim Lauderdale and Soloman Burke, amongst many others.

Buddy Holly never released ‘Crying, Waiting, Hoping’, recording only a demo version that was issued posthumously. It was his first single to be released after his death and got to number 13 in the UK.  

Number 7: Nick Lowe ‘Changing All Those Changes’ (2011)

Nick Lowe has had an extraordinary career as a singer-songwriter, from helping create pub rock in the ‘70s with Brinsley Schwarz, to setting the template for ‘80s new wave with Rockpile, his solo recordings, and his production work for other artists, and from the ‘90s onwards he has been able to redefine himself as a mature singer-songwriter who is not afraid to show his ‘50s and pre-Beatles ‘60s songwriting influences. While Lowe may be one of the UK’s greatest songwriters, he has also been a prolific singer of other writer’s songs, often making them his own.

In his short career, Holly not only laid the foundation for guitar rock, but also defined the role of singer-songwriter, and showed enough self-confidence to want to take control of the direction of his own career, to be an ongoing influence for subsequent generations of artists. In 2011 “Rave On”, a Buddy Holly tribute album, was released with a range of cross-generational artists covering Holly’s songs reflecting his lasting influence. Holly had written ‘Changing All Those Changes’ in 1956 at the Decca Nashville sessions and it was released in 1958.

Unlike some of the other artists on the record, Nick Lowe plays the song very straight, retaining the original rockabilly pop vibe. He was ably assisted by regular band members Steve Donnelly on lead guitar, Matt Radford on bass, and Robert Trehern on drums, and if you hadn’t read the copyright details you would naturally assume that Lowe had written the tune himself.

Number 6: Waylon Jennings ‘Medley Of Buddy Holly Hits’  (1978)

In 1978 Waylon Jennings was at the peak of his commercial success as one of the leading artists of the Outlaw movement, but this success had come at the price of a significant cocaine addiction and a feeling that the Outlaw movement’s original integrity had been compromised by the movements wholesale acceptance by the Nashville of the day. This is the background to his 1978 album, “I’ve Always Been Crazy”, on which Jennings maintained his personal integrity while he questioned his own addictions and wondered about the state of the Outlaw movement. The cover songs on the record were more personal than previous albums and included songs by Johnny Cash and Merle Haggard that had influenced him as a country artist. He also looked back to his time as a member of Buddy Holly’s touring band with a medley of Holly’s hits where he is backed by the remaining Crickets.

In 1958 Buddy Holly arranged Jennings’ first recording session. At the time, Holly was putting a new touring band together and offered Jennings a job playing bass. Jennings was there on that fateful night in 1959 when, due to the bitterly cold weather, Holly chartered a plan to fly the tour to the next gig. Unfortunately, two of the touring party had to continue the tour on the tour bus, and Jennings gave up his seat on the plane to The Big Bopper, who was suffering from flu at the time. This was a life-changing decision, and as well as what is now known as survivor’s guilt, Jennings was also haunted by having joked with Holly, “Well, I hope your ol’ plane crashes”.

After recording and touring with Ric Grech and Albert Lee in the early ‘70s, the Crickets’ profile had once again dipped. However, Jennings’ medley of some of Holly’s biggest hits in arrangements that reflected his own style, helped bring the music to a new audience, as did the 1978 film “The Buddy Holly Story”. The Crickets subsequently toured with Waylon Jennings in the ‘80s for five years.

Number 5: John Prine ‘Oh Boy’ (2004)

You are one of the most respected songwriters and lyricists of your generation, and when you decide to break with the then industry model and form your own fully functional independent label, what would you call your label? In John Prine’s case, he decided on Oh Boy Records, which is a good indicator of the influence Buddy Holly had on his own music.

At the turn of the Century, the three remaining Crickets, Jerry Allison, Joe B. Maudlin, and Sonny Curtis, decided to celebrate their history by inviting fellow artists who had been touched by their music. Two of the first musicians to join the project were Glen D. Hardin, who had been a Cricket himself as well as playing with Gram Parsons, Elvis Presley, Emmylou Harris, Merle Haggard, J.J. Cale and countless others, who played keyboards and the UK’s own guitar legend Albert Lee who played electric guitar throughout the album, and who played with the Crickets in the early ‘70s. Other artists who joined the party to record ‘The Crickets And Their Buddies”  included Waylon Jennings, Rodney Crowell, Nanci Griffith, Graham Nash, J.D. Southern, and Phil Everly.

Buddy Holly recorded his version of ‘Oh Boy’ in 1957 and it was his second single release and was included on “The Chirping Crickets”. The song had been recorded as a demo by fellow West Texas artist Sonny West, who wrote the song with Bill Tilghman, and Norman Petty pitched the song to Holly. The rest, as they say, was history as the song became one of the signature rock & roll songs. It seemed inconceivable that anyone other than John Prine should cover the song on “The Crickets And Their Buddies”, and he was joined by Nanci Griffith and Sonny Curtis on background vocals.

Number 4: Joe Ely ‘The Midnight Shift’  (1980)

In the ‘70s Lubbock became the centre of another musical explosion as a group of local musicians stretched the boundaries of what could be classed as country music. These artists included Butch Hancock, Jimmie Dale Gilmore, multi-media artist Terry Allen, Lloyd Maines, and Ponty Boon.  The artist with the biggest profile at the time was Joe Ely who toured the UK in 1978 and stuck up a surprise friendship with the Clash based on a sense of mutual admiration. The Joe Ely Band toured with the Clash and Ely sang backing vocals on the Clash track ‘Should I Stay Or Should I Go’. “Live Shots” is a live album recorded in 1980 when Joe Ely was touring with the Clash, and it was originally only released in the UK as something of a souvenir album but it turned out to be one of Ely’s best albums.

Buddy Holly recorded ‘Midnight Shift’ in Nashville at Bradley’s Barn in 1956, though the track wasn’t released until 1958 on “That’ll Be The Day”. Sonny Curtis backed him on lead guitar, Grady Martin on acoustic and rhythm guitar, Don Guess on bass, and Doug Kirkham on drums, and ‘Midnight Shift’ was one of the more successful recordings of what came to be known as the Decca Sessions. It was written by Earl Lee and Jimmie Ainsworth and is about a woman who dresses up for the midnight shift and it wasn’t a song about bobby sox and blue jeans.

With “Live Shots” Joe Ely captured the power of his band and his songs, he also tipped his hat to his influences and history, and ‘Midnight Shift’ fit the bill perfectly and is captured in great form.

Number 3: Nanci Griffith ‘Well All Right’ (1996)

Nanci Griffith may have found fame as a folk singer-songwriter but she also had a Texas rock & roll heart. She recorded and toured with the Crickets at various times, and cited Holly’s songwriting and his and Sonny Curtis’s Stratocaster playing as major influences on her own music.  Her experiences of growing up in West Texas provided the raw material for her subsequent songwriting, and Holly and the Crickets were at the centre of that. She said that Buddy Holly and the Crickets’ music had a rhythm, a heart and that you knew who it was as soon as you heard it.

‘Well All Right’ was released as the B-side to ‘Heartbeat’ by Buddy Holly on 5^th November 1958, and was written by Buddy Holly, Jerry Allison, Joe B Mauldin, and Norman Petty, and subsequently released on the 1960 compilation, “The Buddy Holly Story Vol II”. It is a surprisingly modern-sounding song featuring Holly on an acoustic guitar. The lyrics also have an element of protest and being true to yourself, and Nanci Griffith picks up on all this and makes the song her own in a folkabilly way, with the help of Crickets Sonny Curtis and Jerry Allison, leaving no doubt about the influence Holly’s music had on her own. Nanci Griffith’s version was included on the tribute album “Not Fade Away (Remembering Buddy Holly)”.

Number 2: The Bunch ‘Learning The Game’ (1972)

In 1971 it had only been 12 years since Buddy Holly had died, and the pace of change throughout the music industry in the ‘60s had been unprecedented, so much so, that there was a mood at the time amongst musicians to start recognising and celebrating music’s then short history. Australian folk artist Trevor Lucas was looking to move into record production after being in the ‘60s cult band Eclection before forming Fotheringay with his then-wife, Sandy Denny. Sandy Denny was touring with Richard Thompson to promote her “North Star Grassman & The Ravens” album, and the pair joined Fairport Convention’s show at The Rainbow for an impromptu encore which included some rock and roll songs.

Trevor Lucas thought that if he could get the Fairport Convention and Fotheringay extended family into the studio he could give listeners a glimpse of the musicians that listeners hadn’t heard before. This led to everyone going into Virgin Record’s Manor Studio for Lucas’s first production which became “Rock On” by The Bunch. Vocals were shared but Sandy Denny sang lead on the three Buddy Holly covers. Holly recorded ‘Learning The Game’  in 1958, and it was released posthumously in 1960. The version by Sandy Denny is the best track on the album, featuring her plaintive vocals, Richard Thompson’s guitar, and Mighty Babe’s Ian Whiteman on piano with Fotheringay’s rhythm section plus Fairport’s Dave Mattacks on congas.

Number 1: Grateful Dead ‘Not Fade Away’ (1971)

While every Top 10 will have its contentious issues, it wouldn’t be too surprising if there were a number of voices questioning why the Grateful Dead tops this particular list.  That they are one of the great bands of the ‘60s who laid the foundation for americana is not contentious, particularly given the influence their songbook has on current artists, and the clincher is that there was a complete symbiosis between the Grateful Dead and ‘Not Fade Away’, so much so that according to some lists it is the seventh most played song by the band throughout their storied career.

Buddy Holly wrote the song with his manager Norman Petty in 1957, and it was released as the B-side to ‘Oh Boy’, and it was included on Holly’s debut album, “The Chirping Crickets”. The song borrowed Bo Diddley’s rhythm which itself was influenced by African rhythms. The potential of the song was highlighted by the success the Rolling Stones had with it in 1964. The Grateful Dead slowed the song down again and concentrated on the rhythm, the vocals were shared by Jerry Garcia and Bob Weir, and the simpleness of the tune facilitated the potential for the Grateful Dead to jam to their hearts’ content.

There are countless official versions of the song due to the Grateful Dead’s prolific archival release program, but the version included here is the first official release of the song on the live “Grateful Dead” AKA “Skull and Roses” album. This album is central to the Grateful Dead’s development from simply a psychedelic San Francisco band to a rock band for the ages. It included largely cover versions, two new Grateful Dead songs, and one extended jam. While it came after “Working Man’s Dead” and “Americana Beauty”, it is the album that was the entry point for many of their subsequent fans. The Grateful Dead had been playing ‘Not Fade Away’ since 1966 and it was, even then, one of their most popular tunes. It was an end tune played towards the end of a performance and it allowed the band to jam and vary the rhythm. The opportunity to vary the rhythm meant that it was perfect to pair with other tunes, and from ’70 to ’74 it was paired with ‘Goin Down The Road Feeling Bad’, which it is on this version. The song received its last outing on July 5^th, 1995, clear evidence of its staying power as Jerry Garcia’s last show with the Grateful Dead was on the 9^th July. It was such a perfect fit for the Grateful Dead, that there are some people who believe it is now a Grateful Dead song.