The Coolest Song Ever Sung Sarah Vaughan, Portugal, 1973 “Summertime.”

Among the various totems of cool, from dark shades to dance moves, none are as essential to the whole concept as popular songs. More often than not, though, when people describe a song as cool—which, of course, they continue to do every day—they mean that the musicians who play it seem cool to them or that you would be a lot cooler if you liked it. Pop songs themselves are rarely cool. They’re hot—lustful, angry, sad, boastful, celebratory. Passionate, in one way or another. A huge proportion of pop songs are love songs, which insist on the singer’s need or desire for another person. But coolness is not about need and desire. It’s even-keeled. Unflappable.

As Carl Wilson pointed out in the piece that kicked off this series, the term cool itself, in its contemporary usage, is often credited, correctly or otherwise, to Lester Young, a sax player, and its arrival in the mainstream was signaled by the Miles Davis album Birth of the Cool and the West Side Story number simply titled “Cool.” But before Davis’ dad gave his son a trumpet and before Sondheim and Bernstein got nearRomeo and Juliet, George Gershwin wrote a pop aria that captured “cool” better than any song that has come since. It’s called “Summertime,” and you’ve heard it a thousand times.

You’ve also heard it by a thousand people: Last year the New York Times said that there were more than 25,000 different recordings of the tune. That would mean a new one had been made nearly every day since the song was first performed in 1935. I’m not sure I totally believe that. But rest assured that many, many people have recorded this song, and some of them were cooler than others.

None of them were cooler than Sarah Vaughan. And her imperfect, more-than-once interrupted performance of the tune at the Cascais Jazz Festival in 1973 demonstrates the song’s underlying coolness as well as any rendition I’ve seen or heard.

“Summertime” is ostensibly a lullaby; it’s sung to a baby, after all, whom the singer tells to “hush,” in the traditional fashion. Among the songs that seem to have shaped it are “All My Trials,” itself based on a lullaby from the Bahamas and an inspiration for the lyrics, and “Pipi-pipipee,” a Yiddish lullaby. (A Ukrainian lullaby, “Oi Khodyt Son Kolo Vikon,” has also been suggested as a possible source.) Some slower versions of the song emphasize its sleepiness: Ella Fitzgerald was wont to perform it this way, for instance, and so was R.E.M., though not as often. Others elicit its melancholy undertow: Mahalia Jackson, who recorded it as a medley with another of its musical sources, “Motherless Child,” did a sad “Summertime” that cannot be outdone.

Vaughan’s version is cooler, sexier. And when she sang it in Portugal in 1973, at that now-defunct jazz festival founded by the fado singer Jo?o Braga and inaugurated by Miles Davis (among others) two years before, the song’s coolness saved her performance from a bevy of frustrations.

Vaughan opens by nodding to the conditions she’s dealing with. “It’s summertime, and the livin’ ain’t easy,” she sings. (Somewhere, Big Daddy Kane sympathizes.) But then she casually rubs the head of a cameraman trying to sneak by her—the filming of the concert appears to be causing many of her problems—and blows a kiss at someone in the crowd after laughing off a bad bit of feedback. She then has to stop and do something that is, in theory, decidedly uncool: “Watch me,” she tells the crowd, “Look at me.” She gets four more words out before having to stop again and explain to everyone how hard it is for everyone on stage that night.

Throughout all this she’s able to slip in and out of the song like it’s the world’s most comfortable nightgown, each time revealing for anyone with working eyes and ears that not only is she unimpeachably cool—utterly confident and composed under pressure—but that the song itself can sail through any sort of annoyance. A more passionate piece of music, a sadder or happier or angrier song, would need build-up, stage-setting, uninterrupted concentration—it would be nearly impossible for even a performer as masterful as Sarah Vaughan to drop into it again and again the way she does with this song. Each time she rejoins the song, “Summertime” is steady, assured, adaptable.

“Summertime” was originally composed for two (fictional) black women, but it was written by two white men: the Jewish George Gershwin and the South Carolinian Edwin Dubose Heyward, who created the characters, Clara and Bess, who sing it, and composed the lyrics. When the opera it’s a part of, Porgy and Bess, was first performed, Duke Ellington denounced it for “Gershwin’s lampblack Negroisms.”

But he came around. And “Summertime,” which mixed folk and blues and jazz and old Jewish lullabies, and originally aimed to bring peace and quiet to Catfish Row, has been masterfully done for decades by black as well as white performers, by Africansand Americans and by people from every other inhabited continent as well, so far as I can tell. Ellington recorded it, too, more than once. (His bouncy, fragmented instrumental take on Piano in the Foreground is not the coolest recording ever, but it’s one of the more interesting. Give that one a listen, too.) If, as seems likely, the idea of cool as it’s come down to us originated among black Americans and involves dealing with impossible difficulty, then “Summertime” is it, as much as any song could probably be. And Vaughan, who never cared for musical boundaries, and who could make her way through the song despite anything that might befall or bedevil her, is the coolest.

Courtesy David Haglund