Composer Jule Styne and lyricist Sammy Cahn wrote “I Fall in Love Too Easily” for the 1945 film Anchors Aweigh which was a big success for the MGM studio. Co-star Frank Sinatra, who had enjoyed several hits with Styne/Cahn songs, requested that they write the songs for the film in which he introduced the Oscar-nominated song “I Fall in Love Too Easily.” The picture won the Oscar for Best Music and Scoring of a Musical Picture (George E. Stoll). (The movie title is also the title of the song of the United States Navy, composed in 1906 by Charles A. Zimmerman with lyrics by Alfred Hart Miles.)

In 1945* Eugenie Baird with Mel Torme’s Mel-Tones and the Tony Pastor Orchestra took the song to the charts for one week where it peaked at #17. Although his version did not chart, Sinatra recorded the song in 1946 with the orchestra of Axel Stordahl.

(*The date is listed as 1943 in Joel Whitburn’s Pop Memories 1890-1954: The History of American Popular Music.)

In the film Sinatra and Gene Kelly play sailors on leave who meet an aspiring singer played by Kathryn Grayson. Sinatra, a self-confessed bumbling lover, falls for Grayson, and, under the tutelage of ladies man Kelly, he tries to win her affection by offering to get her an audition with a music producer played by Jose Iturbi. The problem is that Iturbi is unknown to either of the sailors. After a few twists and turns of plot, Grayson gets the audition, Kelly gets Grayson, and Sinatra falls for fellow Brooklynite played by Pamela Britton. The film is famous for Kelly’s dance with cartoon character Jerry, the mouse from the Tom and Jerry series.

In The American Musical Film Song Encyclopedia Thomas S. Hischak says, “‘I Fall in Love Too Easily’ is the bewitching ballad...admitting that one’s heart should be ‘well schooled’ in matters of love. Sailor Frank Sinatra mournfully sang it as he played the piano on the large stage of the deserted Hollywood Bowl....”

The lyric perfectly describes the situation--Sinatra’s sudden infatuation with Grayson and his lack of experience in matters of love:

I fall in love too easily
I fall in love too fast
I fall in love too terribly hard
For love to ever last

It is apparent that Grayson, who does not share his infatuation, is not the right girl for him. But perhaps this disappointing experience is just what he needs to prepare him for the right girl when he meets Britton, who promises compatibility and true love.

“I Fall in Love Too Easily” was recorded by Miles Davis in 1963 and 1965; Shirley Horn in a tribute to Miles; trumpeter/vocalist Chet Baker; pianist Bill Evans; and Sammy Cahn himself. Pianists Brad Mehldau and Jacky Terrasson, trumpeter Till Bronner, and guitarist Ralph Towner recorded it in the ‘90s. Since 2000 it has been recorded by vocalists Diane Schuur, Claudia Acuna, and Patricia Barber; the saxophone/piano duo of Jon Gordon and Bill Charlap; drummer Winard Harper; guitarist Romero Lubambo; and pianists Fred Hersch and Christian Jacob.