The song was first recorded on December 17, 1958 by Holly (only himself with guitar) in apartment 4H of "The Brevoort", Fifth Avenue (Manhattan), N.Y.C. After Holly's death on February 3, 1959, his home recordings of his last six compositions were turned over to record producer Jack Hansen. Hansen hired studio musicians and a backup vocal group, the Ray Charles Singers, to augment Holly's vocal and guitar. The idea was to match the established sound of Buddy Holly and the Crickets as closely as possible.
"Crying, Waiting, Hoping" is technically the most successful of the six overdubs; it turned out so well that it was originally intended as the "A" side of a 45-rpm single. Holly wrote and recorded the song with pauses ("Cryin'... waitin'... hopin'... you'll come back"). Hansen ingeniously turned the solo into call-and-response verses, so the backup singers fill in the pauses with an "echo" of each word. (For a German reissue of this song, the producer took the "echo" idea literally, and played the Hansen recording in an echo chamber.)
Hansen's studio version of "Crying, Waiting, Hoping" was recorded on June 30, 1959 at Coral Records' Studio A, along with "Peggy Sue Got Married"). Both sides were released as Buddy Holly's first posthumous single. (The remaining four tunes on Holly's tape were re-recorded by Hansen and company in 1960. All six were issued on an album, "The Buddy Holly Story, Vol. 2.")
Because "Crying, Waiting, Hoping" was popular in England's Merseybeat-scene, the song was recorded by others, including a remake by The Beatles, with George Harrison doing the vocal and replicating studio guitarist Donald Arnone's instrumental bridge, note for note.
Holly's manager, Norman Petty, recorded his own versions of the last six Holly originals in 1964, using his own studio facilities and backup group, The Fireballs. Petty's versions differ from Hansen's versions in that there are no background vocals, and the melodies have new surf-guitar arrangements added to them.
The original, undubbed tape from 1958 has not seen widespread release but has circulated among collectors.
In 1987 Marshall Crenshaw portrayed Buddy Holly in the movie La Bamba, he is featured singing the song on what is supposed to be February 3, 1959, "the day the music died". Crenshaw's version of "Crying, Waiting, Hoping" was produced by Garry Tallent and is featured on the original motion picture soundtrack.