"I Was Such a Fool (to Fall in Love with You)" is a song written by Michael Canosa and Danny Stradella, and was released first as a single in late 1959 by The Flamingos. The song was revived three years later by Connie Francis.Connie Francis, "I Was Such a Fool (to Fall in Love with You)" single release Retrieved May 5, 2023
The Flamingos version The Flamingos released the original version of the song as a single in December 1959, with the recording session produced by George Goldner. Their version reached No. 71 on the Billboard Hot 100 chart the next year.The Flamingos, "I Was Such a Fool (to Fall in Love with You)" chart positions Retrieved May 5, 2023 It was ranked higher on the Cashbox Top 100 Singles, where it peaked at No. 67.
Connie Francis version Background
In early 1962 "Don't Break the Heart That Loves You" had become Francis' third and final single to top the Billboard Hot 100 and the Billboard Easy Listening charts. The single also rose to high positions on international charts as well. After the chart-topper, she would have two more top ten singles and later "I Was Such a Fool (to Fall in Love with You)", a familiar ballad like singles before, was scheduled to release in the fall of 1962. The recording session was arranged and conducted by Bill McElhiney.
Release and reception "I Was Such a Fool (to Fall in Love with You)" was released as a seven-inch single in September 1962 by MGM Records. It was backed by a country song, "He Thinks I Still Care" on the B-side, which was lifted from her album Country Music Connie Style released earlier that year. It was produced by Danny Davis. "I Was Such a Fool" would make its album debut three years later on Connie Francis Sings "For Mama".
The single received a positive critical reception upon its release. Cashbox stated that "The lark, who just has a solid sales “Vacation,” heads into the Fall months with a double-decker that's sure to be all over the charts in no time flat. One half, “He Still Thinks I Care,” is a lilting, crying towel ‘answer’ to the recent George Jones country smash. “I Was Such A Fool” is a beat-ballad new comer also from the weeper dept."Cashbox magazine, Record Reviews, Pick of the Week. 1962, page 12. Billboard believed that it was "two more powerhouse sides from Connie." Saying "Both are in the ballad groove," continuing that "He Still Thinks I Care" is a "moving weeper done with country touches against chorus and ork", and called "I Was Such a Fool" a "tender ballad which the lass emotes over tasteful backing."Billboard magazine "Singles Reviews", September 29, 1962. Page 27, retrieved January 27, 2026
Chart performance "I Was Such a Fool (to Fall in Love with You)" debuted on Billboard magazine's Easy Listening chart on September 20, 1962, peaking at No. 8 during a seven-week run on the chart. The single didn't reach the top 10 on the Billboard Hot 100, although it reached the top 40, and peaked at No. 24 on the chart.Connie Francis, "I Was Such a Fool (to Fall in Love with You)" Chart Positions Retrieved May 5, 2023 On Cashbox magazine's Top 100 Singles chart the single was ranked higher, peaking at No. 18. The single also reached No. 19 on the Music Vendor 100 Top Pops chart. The single also sold well in Canada, reaching No. 32 on the CHUM charts. "He Thinks I Still Care" reached No. 26 the next week on the same charts.
Charts
Connie Francis version Chart (1962) Peakposition US Billboard Hot 10024 US Billboard Easy Listening8 US Cashbox Top 100 Singles18 US Music Vendor 100 Top Pops19 Canada CHUM Hit Parade32
The Flamingos version Chart (1960) Peakposition US Billboard Hot 10071 US Cashbox Top 100 Singles67
References