Roy Orbison’s Favorite Buddy Holly Song Was Recorded During His Final Studio Session and Released Weeks Before His Death in 1959

In 1957, Buddy Holly also recorded two of Roy Orbison’s songs on his debut, The “Chirping” Crickets, “You’ve Got Love,” and “An Empty Cup (And a Broken Date).” The latter, a story of a jilted date, was a track Orbison first recorded with his early band, the Teen Kings, in 1956, but never released as a single. Orbison later co-wrote a third song for the Crickets’ first album in 1962, featuring Bobby Vee, following Holly’s death.

Both teens from West Texas, Holly and Orbison, became friends in the mid-1950s, along with a friendly rivalry, and even played some shows together during the late ’50s. Orbison also turned Holly on to producer Norman Petty’s Studios in Clovis, New Mexico, where he and the Crickets would record most of their hits between 1957 and 1958, including “Peggy Sue,” “Not Fade Away,” “That’ll Be the Day,” and more.

By 1958, Holly also connected with Paul Anka after the two toured together as part of the “Biggest Show of Stars for 1957,” also known as the “Cavalcade of Stars” bus tour, alongside Fats Domino, Chuck Berry, Eddie Cochran, and the Everly Brothers. A fan of Anka’s 1958 song “You Are My Destiny,” Holly asked his friend to write him a song, and Anka obliged, delivering the sentimental pop ballad “It Doesn’t Matter Anymore.”

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[RELATED: Paul Anka Wrote One of the Final Songs Buddy Holly Recorded, Released a Month Before His Death, and Covered 20 Years Later by Don McLean]

“Rainging in My Heart”

The song was released on January 5, 1959, weeks before Holly’s death in a plane crash, along with the B-Side, “Raining in My Heart,” written by Felice and Boudleaux Bryant, the songwriting duo behind the Everly Brothers’ hits “Bye Bye Love,” “All I Have to Do Is Dream,” “Wake Up Little Susie,” and more.

Buddy Holly recorded both songs in New York City at Pythian Temple Studios on October 21, 1958, during his final studio session before his death in a 1959 plane crash, but it was the B-side that reportedly became Orbison’s favorite song by his friend.

The lyrics of “Raining in My Heart” follow the overcast feeling of loneliness following a breakup.

The sun is out
The sky is blue
There’s not a cloud
To spoil the view
But it’s raining
Raining In My Heart

The Weather Man
Says “Clear today”
He doesn’t know
You’ve gone away
And it’s raining
Raining In My Heart

“Raining in My Heart” was also released a month after Holly’s death on the posthumous compilation, The Buddy Holly Story, in March 1959.

In 1978, Holly’s song later became a hit for British singer-songwriter Leo Sayer, who already had a No. 1 hit that year with “You Make Me Feel Like Dancing.” Sayer’s version of “Raining in My Heart” peaked at No. 21 in the UK and No. 9 on the Easy Listening chart in the U.S.

Photo: Roy Orbison, October 14, 1964. (Evening Standard/Hulton Archive/Getty Images)