"My Funny Valentine” is a love song with no illusions

Lorenz Hart, who struggled with drinking, career stress, and loving people who didn't love him back, wasn't theorizing when he wrote "My Funny Valentine." That matters if you want to understand why the song feels so different from most Valentine's Day tunes.

Richard Rodgers wrote the melody in 1937 for Babes in Arms, but it's Hart who gives the song its lasting weight. Already deep into the sharper, more raw phase of his writing (and life), Hart avoided the sugar that Broadway audiences expected.

Lorenz Hart in 1936

The song was written for Mitzi Green to sing to a male character named Valentine LaMar. It wasn't conceived as a big, direct declaration of love. It was more like admitting your feelings while pretending to do something else.

That original context explains the tone. Yes, there's affection here, but it comes with clear eyes, a little sharpness, and some self-protection built in. Hart isn't idealizing a beloved from across a sunlit field. He's sitting in a dark corner of a bar watching from afar. He's noticing flaws, habits, and insecurities and choosing them anyway.

The lyrics say this right away. "My funny Valentine / Sweet comic Valentine" sounds playful. But then comes: "Your looks are laughable / Unphotographable." There's no metaphor to soften the blow, no poetic fog. It's love without retouching (or maybe love that insists on removing the filter entirely? It’s hard to say). An interesting bit of trivia: some early performers quietly altered or skipped lines like "Is your figure less than Greek?" when tastes changed. Hart's original phrasing is intentionally blunt, even awkward. The clumsiness is the point. Real love is rarely elegant.

The emotional center of the song isn't romance so much as sticking by someone even when you see them completely. "Don't change a hair for me" is often sung tenderly now, but on the page it reads almost like a warning. Hart isn't asking someone to become better, shinier, or easier to love. It's the plea of someone who has watched people twist themselves into different shapes to earn affection and lose themselves along the way.

Chet Baker sings - released in 1954

When jazz singers later took hold of "My Funny Valentine," the song shed its theatrical skin and became something more intimate. Chet Baker's versions, in particular, sound like a late-night admission rather than a performance. He presents it all so beautifully: delicate, hesitant, and a little exposed.

Even Frank Sinatra, who could easily have turned the song into a grand romantic statement, tended to slow it down, letting the lyric's harder truth show through.

Ernest Hemingway once said the hardest thing in the world is to write straight, honest prose about people. Hart managed something similar in just these few verses. He stripped love of its ornamentation and left what remained. "My Funny Valentine" sticks around not because it promised love will save you, but because love sees you for who you are and chooses to stay anyway.