Some songs arrive as afterthoughts and leave as standards. “Raining in My Heart” was written by Nashville’s most successful husband-and-wife songwriting team, recorded by Buddy Holly at the very last studio session of his life, and then — almost casually — tucked away on the B-side of another song. It peaked at a modest number 88 in America. Yet twenty years later, Leo Sayer pulled it out of the Holly catalogue, dressed it in the soft California production of Richard Perry, and carried it back into the charts on both sides of the Atlantic: number 21 in Britain, number 47 on the Billboard Hot 100, and number nine on the US Easy Listening chart. It remains the definitive demonstration that a great ballad does not expire — it simply waits for its next singer.
Written by Nashville’s Royal Couple
The song came from Felice and Boudleaux Bryant, the husband-and-wife team who were among the most successful songwriters in Nashville history. The Bryants built their reputation supplying hits to the Everly Brothers and a string of country and pop acts, and they had a particular gift for the bittersweet ballad — songs in which the singer smiles in public and falls apart in private. “Raining in My Heart” is built on exactly that contrast. Its narrator looks out at a beautiful day — sunshine, blue skies — and feels none of it. The weather in the lyric is fine; the weather in the singer is not. It is a simple device, but in the Bryants’ hands it was strong enough to hold a melody that singers are still borrowing more than six decades later.
The song found its first and most famous interpreter quickly. Buddy Holly, then in the middle of reinventing himself, had split with his producer Norman Petty and relocated to New York. He was writing, experimenting, and — crucially — listening to what a bigger canvas might do for his music. A lush Bryant ballad was an ideal test piece.
Holly’s Last Session: The String Sessions
On 21 October 1958, Holly walked into Decca’s recording studio in the Pythian Temple on West 70th Street in New York City for what would become his final studio session. Coral Records’ new head of artists and repertoire, Dick Jacobs, produced and conducted, and behind Holly stood an eighteen-piece ensemble drawn largely from former members of the NBC Symphony Orchestra — violins, violas, cellos and a saxophone section that included Boomie Richman. Fans have come to know the date simply as “the string sessions.”
In roughly three and a half hours, Holly recorded four songs. Alongside “Raining in My Heart” — Holly’s version runs just 2:48 — the session produced “True Love Ways,” written for his wife María Elena, who was present in the studio, and “It Doesn’t Matter Anymore,” the Paul Anka song that would become the A-side of Holly’s next single. It was a remarkable afternoon: a 22-year-old rock and roller, a music the business still considered a teenage fad, standing in front of an orchestra and singing like a crooner. Holly was moving toward the kind of orchestrated pop that singers such as Bobby Darin would soon make fashionable. He simply ran out of time.
A B-Side in a Tragedy’s Shadow
Coral released the single (catalogue number 9-62074) on 5 January 1959. “It Doesn’t Matter Anymore” took the A-side; “Raining in My Heart” was placed on the flip. Less than a month later, on 3 February 1959, Holly was killed in a plane crash in Iowa, aged just 22 — the date Don McLean would later immortalise as “the day the music died.” The single charted in the shadow of that loss: as a double-sided release it climbed through the spring, with “Raining in My Heart” credited with a peak of number 88 on the Billboard chart. In March 1959 the recording was included on The Buddy Holly Story, the posthumous compilation that introduced Holly’s music to much of its future audience.
As chart positions go, number 88 is a footnote. But B-sides have long memories. The recording’s tenderness — Holly’s voice floating over Jacobs’ strings, the ache in the lyric never quite breaking the song’s composure — kept it alive in the Holly catalogue, and singers kept finding it. Skeeter Davis included it on her 1967 tribute album Skeeter Davis Sings Buddy Holly. Dean Martin recorded it for For the Good Times in 1971. The Dave Clark Five cut it the same year. The song was becoming what the Bryants had quietly designed it to be: a standard, available to any singer with the voice and the heartbreak to carry it.
Twenty Years On: Sayer Finds It
Leo Sayer arrived at the song at a turning point in his own career. His 1976 album Endless Flight, produced by Richard Perry, had given him two American number ones, “You Make Me Feel Like Dancing” and “When I Need You,” and Thunder in My Heart (1977) kept the run going. For his sixth album, the self-titled Leo Sayer, released on 11 August 1978, Sayer and Perry deliberately changed the temperature. The record — described in its genre billing as country pop — leans into mellow, song-centred material, much of it other people’s songs: Jackson Browne’s “Something Fine,” Andy Fairweather Low’s “La Booga Rooga,” the Amazing Rhythm Aces’ “Dancing the Night Away,” and, closing side one, the Bryants’ “Raining in My Heart.”
Contemporary reviewers noticed the shift. Toronto’s Globe and Mail observed that Sayer had “fully abandoned” his earlier pop-disco style and was offering “a plate full of mellow tunes, geared primarily to show off his vocal chords.” AllMusic, looking back, judged the album “one of the artist’s most respectable in a large body of good work,” and British buyers sent it to number 15 and a Gold certification.
Sayer’s “Raining in My Heart” runs 3:16 — nearly half a minute longer than Holly’s — and the extra space is the point. Where Holly’s record is a young man’s promise, all strings and held breath, Sayer sings it as an adult standard: unhurried, polished, and built for the adult-contemporary audience that Perry knew how to reach. The lyric’s contrast does the emotional work; Sayer simply stands in the middle of it and lets his high, clear voice register both the sunshine and the rain.
A Quiet Transatlantic Hit
Released as a single in the United States in September 1978 — with Sayer’s own “No Looking Back,” the album’s closing track, on the B-side — the record performed exactly as its makers hoped. In Britain it reached number 21 on the UK Singles Chart. In America it climbed to number 47 on the Billboard Hot 100 and number 43 in Cash Box, but its real home was the easy listening audience: number nine on Billboard‘s Easy Listening (Adult Contemporary) chart and number ten on Canada’s RPM Adult Contemporary listing. It even crossed over to number 63 on Billboard‘s Hot Country Songs chart — a fitting nod to the Bryants’ Nashville roots — and reached number 26 in Ireland.
Those numbers tell a particular story about Leo Sayer in 1978. He was no longer only the exuberant hitmaker of “You Make Me Feel Like Dancing.” With records like this one, he was building the second career that would sustain him for decades: the interpreter, the balladeer, the singer trusted voices on adult radio turned to when a song needed tenderness rather than fireworks.
The Song That Wouldn’t Dry Out
Sayer’s hit was not the end of the song’s travels — it was barely the middle. Anne Murray recorded “Raining in My Heart” for her 1979 album New Kind of Feeling, a year after Sayer’s single. Peter Skellern took it up in 1980, Connie Francis included it on her 1996 Holly tribute With Love to Buddy, and Status Quo covered it on their 1996 album Don’t Stop. Hank Marvin recorded an instrumental version on Hank Plays Holly, and in 2011 Eric Idle contributed a deliberately Spike Jones-flavoured rendition to the tribute album Listen to Me: Buddy Holly.
The song had also, quietly, entered the bloodstream of the Beatles. Their 1963 recording “Please Please Me” carries the line “there’s always rain in my heart” in its bridge, and in 1968 “Dear Prudence” opened by paraphrasing the Bryant lyric’s sunny-day setup — the sun up, the sky blue — a debt hiding in plain sight on the White Album. In 1984 Alvin Stardust built an entire hit around the feeling, singing “I feel like Buddy Holly, ’cause it’s raining in my heart.”
And the chain continues back to Sayer himself: nearly half a century after his single, the song still appears in his live setlists, performed on tour as recently as 2025. That is the real measure of “Raining in My Heart.” A B-side that peaked at number 88 became, through Holly’s strings, the Bryants’ craftsmanship and Sayer’s second-act reinvention, one of those rare ballads that every generation of singers seems obliged to test itself against. The forecast in the lyric never changes. Neither, apparently, does its appeal.