Richard Linklater’s 2025 movie Blue Moon broadened interest in the composer Richard Rodgers (played by Andrew Scott) and the lyricist Lorenz Hart (played by Ethan Hawke, who was nominated for an Oscar). With a title taken from one of the songwriting duo’s most famous compositions, Blue Moon depicts the pair in 1943, shortly before the end of their partnership and Hart’s life.
Rodgers and Hart‘s partnership lasted 24 years and yielded three dozen stage and film productions. Among the stage productions was the 1937 musical Babes in Arms, and among that show’s standout songs was the subject of this article, the odd little romantic tribute “My Funny Valentine”.
In the song, a female character named Billie Smith addresses her male love interest, Valentine “Val” LaMar, as “my funny valentine / Sweet comic valentine.” No, Billie doesn’t sing “Valentine”. Ignore versions of the lyrics that capitalize it into a proper noun. The lowercase “valentine” is per Rodgers’s official website (with Oscar Hammerstein as Rodgers’s lyricist after Hart). The lowercase form means Billie is using the noun to pun on Valentine’s name, referring to him as her valentine. In the song’s last line, Billie fuses the two meanings, declaring that “Each day is Valentine’s Day.”
The creative team behind Babes in Arms clearly knew the power of “My Funny Valentine”. According to Wikipedia, it was after the song had been written that the character’s name was changed to match.
Hart’s lyrics for “My Funny Valentine” fascinate mainly because of this love song’s most unusual aspect. Instead of flattering descriptions of the beloved, the singer offers negative observations, such as “Your looks are laughable / Unphotographable” and “Is your figure less than Greek? / Is your mouth a little weak? / When you open it to speak / Are you smart?” The singer may be having fun, but if the song is performed outside the original show’s context, it’s easy to imagine the unnamed valentine being unpleasantly surprised and dryly replying, “Gee, thanks.”
Meanwhile, Rodgers’s uncannily beautiful melody provides challenges. For example, in “When you open it to speak,” the singer must reach for a higher note on the word “open”, imitating the awkwardness of the valentine’s facial movement. That struggle creates a pause, a moment of waiting and anticipation, like the one before the valentine speaks. Whether that something will be smart or not could go either way.
Mitzi Green’s rendering of “My Funny Valentine” in the 1937 production of Babes in Arms wasn’t recorded. However, in a 1999 production, Erin Tilly re-created that version using the original arrangement. Tilly’s rendition is sweetly loving, formal, with perfect diction, appropriate for the mainstream stage in 1937. On the word “open”, Tilly performs a feat, going operatic.
That version includes the introductory verse, which many subsequent renditions omit. For one thing, the language is gendered. For another, the language is tongue-in-cheekily Shakespearean, not in the song’s otherwise languorous mode: “Behold the way our fine-feathered friend / His virtue doth parade / Thou knowest not, my dim-witted friend / The picture thou hast made / Thy vacant brow and thy tousled hair / Conceal thy good intent / Thou noble, upright, truthful, sincere / And slightly dopey gent – / You’re…”
Omitting that introductory verse means the performer can launch right into the piece’s memorable melody.
The introduction isn’t included in the song’s first actual recording, an instrumental. In 1937, Fairchild and Carroll and Their Orchestra jauntily accentuated the positive on one side of a 78-rpm shellac record.
Two years later, Babes in Arms became a movie musical starring Judy Garland and Mickey Rooney. This adaptation omits nearly all the Rodgers and Hart songs, including “My Funny Valentine” (welcome to Hollywood). On YouTube, an AI version claims to be what Garland might have done with the song, but the “voice” sounds nothing like Garland’s (welcome to AI), and the “arrangement” recalls Ella Fitzgerald‘s utterly classy take, from her 1956 collection Ella Fitzgerald Sings the Rodgers and Hart Songbook.
Probably vying with Fitzgerald’s for most canonical recording is Frank Sinatra‘s 1954 rendering. That one shifts from elegance into swinging, as Sinatra’s breezy playfulness places personal style over spot-on interpretation. Fitzgerald plays it straight, fully inhabiting the song.
Instrumental versions of the tune can’t quite inhabit it, but they may explore the idea of narrative context. That is, with what color or colors do they paint the melody? In 1952, jazz saxophonist Gerry Mulligan’s Quartet, featuring Chet Baker on trumpet, set the template for a far more downbeat rendering, which also omits the introduction. The tune became a signature piece for Baker.
On his 1960 album Exotic Sounds Visit Broadway, exotica pioneer Martin Denny brought Broadway into his space-age bachelor pad. If this isn’t the weirdest interpretation of “My Funny Valentine”, it’ll do until the real thing comes along. Denny treats the introduction as Elizabethan, then shifts into an Asian music-box vibe, then into easy listening, then back to Asian:
The Miles Davis Quintet recorded a somewhat uptempo “My Funny Valentine” in the studio in 1957. With a different Quintet, Davis recorded his most famous version in 1964. As his former compatriot John Coltrane did with Rodgers and Hammerstein’s “My Favorite Things” in 1961, Davis stretched out, tunneling into feelings that other versions barely hint at.
Rodgers wouldn’t have recognized some of the melodic variations on display in that version. However, the complex melancholy would have been familiar to Hart.
As depicted in Linklater’s movie, Hart was painfully self-conscious about his physicality (extremely short, unhandsome, balding), romantically and sexually thwarted, and alcoholic. In writing the unflattering portions of the lyrics, he might have drawn on personal experience. Perhaps the redemptive lines, such as “Yet you’re my favorite work of art”, represented the writer’s wishful thinking. Penning the punning “You make me smile with my heart” must have delighted Hart.
From 1961’s The Soulful Moods of Marvin Gaye, the soul man’s first album, here’s a version that acknowledges the pain but, in its old-fashioned neo-doo-wop tempo and implied smiles, celebrates the redemption. Picture Gaye sitting across a restaurant table from the date he has been pursuing:
The lyrics’ tension between acknowledgement of flaws and abiding love results, by the end, in a breathtaking acceptance: “But don’t change your hair for me, / Not if you care for me. / Stay, little valentine, stay.” Four decades later, a songwriter versed in the Great American Songbook drew, consciously or not, on that conclusion for this latter-day standard.
Around the same time that Billy Joel was channeling his inner Rodgers and Hart, Elvis Costello was riding the new wave. In 1980, he released a promotional single of his and the Attractions’ 1978 cover of Nick Lowe‘s “(What’s So Funny’ Bout) Peace, Love, and Understanding”. Costello and Lowe, his producer at the time, must have laughed about covering “My Funny Valentine” on the flip side of that single, providing two sides of “Funny.” However, the singer injects no irony into “My Funny Valentine”, taking the opportunity to exhibit his vocal dexterity. At around a minute and a half, adding no frills, not repeating the whole thing as is customary, Costello’s solo version may be the shortest and most arresting.
In 1983, the UK rock band My Bloody Valentine became a shoegaze sensation with their pummeling interpretation of their near-namesake tune. OK, that’s not true. Hart would probably have loved the twist on his title in their name, but to the best of my knowledge, MBV never covered a Rodgers and Hart song. They named themselves after the 1981 horror movie, whose title was inspired by the song.
However, on the indie-rock side, the chanteuse Nico, a goth favorite, covered the song on her 1985 album Camera Obscura. While possibly the most Germanic rendering not performed in a beer hall, and including a “professional” singer’s least successful struggle to reach that high note on “open”, plus a not-too-confident closing note, Nico’s take reveals a surprisingly romantic heart. Much credit goes to producer John Cale, keyboardist James Young, and trumpeter Ian Carr.
From a different universe comes Chaka Khan’s version, originally included on 1995’s Waiting to Exhale soundtrack. Amidst spacious production and smoothly soulful grooves largely by Babyface, Khan funks up the melody, leading to a version that most likely would not have been approved of by Richard Rodgers, had he been alive to hear it. Her roar on “open” displays Khan’s characteristic fearlessness:
Rodgers might have been far more comfortable with Rufus Wainwright’s take. For Sweetheart, a 2005 multi-artist compilation of love-song covers, Wainwright drew inspiration from Ella Fitzgerald’s version. He includes the introductory verse, but replaces the orchestration with solo piano. In terms of spare sonics, this version recalls Elvis Costello’s, but Wainwright effortlessly works in some melodic variations that Miles Davis might have envied.
Two decades and however many interpretations later, Sung Holly shows that delicate guitar notes, crystalline voice, and commitment can cast a “My Funny Valentine” spell.