"Lonely Teardrops" is a song recorded and released as a single in 1958 by R&B, Soul, and Rock n Roll singer Jackie Wilson on the Brunswick label. It is a 1999 Grammy Hall of Fame Inductee. The song became an across-the-board national Top 10 Pop smash (# 7),a # 1 hit on the R&B charts, and is ranked #315 on Rolling Stone magazine's list of The 500 Greatest Songs of All Time. It is ranked as the 57th biggest U.S. hit of 1959. "Lonely Teardrops" is also listed on the Rock and Roll Hall of Fame's list of "The 500 Songs that Shaped Rock and Roll".

Written by Berry Gordy Jr.,Gwendolyn Gordy (Berry's sister) and Roquel "Billy" Davis, going under the pseudonym Tyran Carlo, the single, alongside Wilson's debuting five consecutive singles between 1957–58, turned Wilson into an R&B superstar and influenced the later careers of Davis, who joined the staff of Chess Records while Gordy used the money from the song's success to form Motown Records within a year. The song raced up to number one on the Billboard R&B chart and became Wilson's first top ten hit on the Billboard Hot 100, eventually peaking at number seven. It was originally intended by Gordy to be recorded as a ballad. After recording it, Wilson and Brunswick executives felt the song lacked something. It was then given to veteran Decca Records arranger Dick Jacobs who re-arranged it into the smash hit it became. The hit's success helped land Wilson on American Bandstand and The Ed Sullivan Show performing to receptive audiences on the respective shows, as well as other shows such as Shindig and Hullabaloo.

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