Chaka Khan in Berlin in 1995
Chaka Khan in Berlin in 1995 © Ullstein Bild

The 1937 Rodgers and Hart musical Babes in Arms, which gave generations of grateful cabaret singers "My Funny Valentine", also virtually invented the "Hey, let's put on a show!" genre. They did childcare differently in those days — in the musical, a group of home-alone teens must do something useful with their time to stop the local sheriff carrying out his threat to send them to the work farm. This is the Great Depression, and the parents are off working the vaudeville circuit.

The plot was flimsy and later much parodied, but the show produced several classic hits: "The Lady Is a Tramp", "Where or When" and "I Wish I Were in Love Again". "My Funny Valentine" became such a ubiquitous torch song over the years that, as the writer Alec Wilder noted in American Popular Song (1972), the owner of one New York club "inserted in all contracts with vocalists a clause which stated they were forbidden to sing it".

The original Rodgers and Hart number was sung by a female lead, fondly listing the faults of the lead male, Valentine LaMar. "Is your figure less than Greek? Is your mouth a little weak?/ When you open it to speak, are you smart?" But deeper feelings are revealed when the rhythm kicks in and she sings the refrain: "You're my funny Valentine, sweet comic Valentine / You make me smile with my heart".

A Variety reviewer worried that "no nudity, no show girls, no plush or gold plate may mean no sale", but the 1937 Broadway show stretched to 289 performances.

In 1939 Busby Berkeley directed a film version of Babes in Arms starring Judy Garland and Mickey Rooney. However, both plot and songs were drastically altered; "My Funny Valentine" was one of nearly a dozen numbers set adrift. It resurfaced in the 1957 Frank Sinatra and Rita Hayworth vehicle Pal Joey, lip-synced by Kim Novak in a nightclub setting, imbuing the song with the bittersweet hints of doomed romance that were to remain its stock-in-trade.

Chet Baker in the mid-1950s
Trumpeter Chet Baker in the mid-1950s © Metronome

Meanwhile, the composition made slow but steady inroads into the jazz repertoire. The song charted briefly with a sweet-toned big-band version recorded by the Hal McIntyre Orchestra in 1944. As became the norm, the introductory verse was removed and the band cut straight to the bittersweet refrain.

Baritone saxophonist Gerry Mulligan picked it up for his Quartet in 1952 and the austere, piano-free reading was the perfect vehicle for Chet Baker's trumpet. Among the many instrumental versions around, pianist Bill Evans and guitarist Jim Hall's up-tempo duet on the 1962 album Undercurrent stands out.

In 1954, Sinatra included it on Songs for Young Lovers, his first collaboration with bandleader Nelson Riddle. Baker recorded the tune again — this time as a vocalist — on his 1956 hit album Chet Baker Sings, and revisited it many times over the years, especially in live performance.

The song had gone mainstream, and the consensus on how many artists recorded it stands at about 600. Ella Fitzgerald recorded the song in its entirety — a rare thing — in a pristine 1957 cover featuring the Buddy Bregman Orchestra.

'My Funny Valentine' vinyl record

Miles Davis also made the song part of his repertoire and recorded it several times. The best is a live 1964 concert recording of a fundraising benefit for black voter registration in Mississippi. It is a 15-minute shape-shifting, mood-changing masterpiece.

A Babes in Arms subplot concerned a wealthy southerner bankrolling the show on the proviso that two African-American kids were sacked from the cast. So it's pleasing to note that a Chaka Khan account of "My Funny Valentine" was part of the award-winning soundtrack of the 1995 Whitney Houston movie Waiting to Exhale, which featured an all African-American cast.

But it is with Baker that the song has come to be most identified. In a nightclub scene in the 1999 film The Talented Mr Ripley, Matt Damon's Ripley performs a version, closely emulating Chet Baker's singing style to conjure a tangible sense of the late 1950s. A song that started life in a Depression-era musical comedy ended up associated with the boom years and a musician, Baker, whose life ended in tragedy.

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Photographs: Metronome; Ullstein Bild

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