It’s almost Valentine’s Day, so it’s time to brush up on your favorite love songs. Today, we’re taking a look at one of the most popular romantic tunes ever written: “My Funny Valentine.”

Written by the legendary duo Richard Rodgers and Lorenz Hart, the song was published in 1937 as part of the musical “Babes in Arms.” Like many standards of the Great American Songbook, that was just the beginning of its story.

According to The Whole Note, the song has been recorded over 1,600 times by more than 600 artists of all genres, from Frank Sinatra to Paul McCartney to Ray Charles. “My Funny Valentine” especially found favor with jazz musicians, who used the melody and chord changes to improvise their own ideas. It became a signature tune for vocalist and trumpeter Chet Baker, whose melancholic phrasing perfectly matched the song’s vibe. 

He first recorded it in 1954, but even later in life, he had a special connection to the song. Check out this performance from Tokyo in 1987.

You don’t need a degree in music theory to notice how unusual this song is for a standard love song. While we associate major sounds with happiness and love, “My Funny Valentine” is primarily minor. K. J. McElrath, musicologist for JazzStandards.com, notes that the song is 70% minor and 30% major, primarily during the bridge and tag sections. It also has a harmonic hook.

“The harmonic progression of the ‘A’ section is led by a chromatically descending bass line that changes each chord (somewhat reminiscent of ‘In A Sentimental Mood’ and ‘Blue Skies’),” he writes. “In the original key, it looks like this: Cm – G7/B –Eb/Bb – Am7(b5) – Ab – Eb/G – Fm – Eb – Dm7(b5). From the last chord, it is an easy return to C minor.”

The shifting chords make the perfect foil for the song’s simple, mostly stepwise melody, and the minor tonality reinforces the lyrics, which elaborate on an imperfect love that celebrates a partner’s imperfections rather than idealized beauty.

“Larry Hart, not unlike Randy Newman (who is Rodgers to his own Hart), delighted in dimensional human songs that reveal the realities of real people, replete with real human failings,” American Songwriter explains. “Hart wrote what can be considered an ‘I love you anyway’ love song lyric; rather than idealize the beloved, it does the very opposite, even specifying their foibles and fumbles, yet concluded with a declaration of love. As if to say, I love you – in spite of all the things you are.”

These unique attributes help to explain why “My Funny Valentine” endures nearly a decade after its debut. Rodgers and Hart built a song that acknowledges the messiness of real relationships. It’s this realness that helps artists connect to the music. Every time Chet Baker performed “My Funny Valentine,” he was reflecting a part of his life.

Now it’s your turn to express yourself. Get the lead sheet for “My Funny Valentine”: