Carmen McRae was a good friend of Monk’s, and for my tastes, she sings this song better than anyone. Her tart, unsentimental intellect matches Monk’s own approach to music perfectly. Here she is performing “Round Midnight” in 1962.

Monk wrote his biggest hit back in the late 1930s, but he didn’t have a recording contract at the time and couldn’t get anyone else interested. A few years later, however, his luck changed. His friend Bud Powell was playing piano in a band led by former Ellington Orchestra trumpet star Cootie Williams. Powell convinced Williams to record “Round Midnight” in 1944.

The record made an impact, and “Round Midnight” became Cootie Williams’ theme song. Other musicians became interested in the tune as well. Dizzy Gillespie did a recording in 1947, for which he wrote his own distinctive intro and ending.

Monk himself liked Dizzy’s intro and ending so much that he promptly began including them in his own performances of his tune.

Later in 1947, Monk finally got to record his tune for the first time.

Much as I love Monk’s own playing, this recording is an awkward one, with a lame-sounding film noir arrangement in the horns. Fortunately, Monk recorded “Round Midnight” many more times over the course of his life. He tended to play it quite a bit faster and more abstractly than other interpreters. Here’s a live version from sometime in the sixties.

Monk’s best recordings of the tune were solo piano versions. My favorite is the one on The Composer, which sadly isn’t available on YouTube. The one on Thelonious Himself is good too.

The definitive version of “Round Midnight” is the one by Miles Davis, as recorded on his 1957 album ‘Round About Midnight (a widely used alternate name for the tune.)

Miles honed this arrangement in performances for years before finally recording it. He plays Dizzy’s intro on muted trumpet, in a severely stripped-down form. His take on the melody is similarly minimalist, using many fewer notes than the original. At the end of the head at 2:40, Miles inserts a whole new section of his own invention, a shout chorus that jumps unexpectedly into major tonality, played on unmuted trumpet. The shout chorus sets up John Coltrane’s assertive and energetic tenor sax solo. Then Miles brings the mood back down with his muted take on Dizzy’s ending. This recording was a jukebox hit in black neighborhoods, and it went a long way toward cementing Miles’ iconic status in the jazz world. If you had to explain jazz to a visitor from outer space, you could do worse than this recording.

Every jazz singer has attempted “Round Midnight” at one point or another. To pick one of many great versions, here’s Ella Fitzgerald, accompanied by Oscar Peterson.

As do most singers, Ella omits the intro and ending. The most complete vocal version, and maybe the most beautiful, is by Carmen McRae again, from her highly recommended 1988 album Carmen Sings Monk.

Everything’s here: all the sections, with the melody as written and also as interpreted by Dizzy Gillespie, all with lyrics. This, as far as I’m concerned, is the last word on “Round Midnight” — at least until the next evolution.

Hip-hop might point the way forward. The intro to Luchi De Jesus‘ recording of “Round Midnight” is sampled in “A Friend” by KRS-One.

Want to try playing “Round Midnight” yourself? It’s well worth it, you’ll learn a lot about music that way. The problem is finding a decent chart. Be warned that some of the chords in the infamous Real Book version are wrong, and it also omits Dizzy’s intro and ending. A more accurate transcription can be found in Hal Leonard’s lovingly rendered Thelonious Monk Fake Book, but that chart also leaves out the intro and ending. When I did the tune with my former jazz group, I decided to just transcribe the missing sections myself. Feel free to download my chart here.

Any crucial versions I missed? Leave them in the comments.

“Moody’s Mood” went on to inspire further analog remixing. In 1952, Eddie Jefferson wrote lyrics to Moody’s solo, and King Pleasure recorded them in 1954 with Blossom Dearie. Here’s Moody himself singing the Eddie Jefferson lyrics with Dizzy Gillespie – he sings Blossom Dearie’s part too:

Also, here’s a delightful performance of “Moody’s Mood” from the Cosby Show (sorry, no embedding.)

The vocal version of “Moody’s Mood” inspired a lot of singers, inside and outside of jazz. Jon Hendricks cites it as his central inspiration for the formation of Lambert, Hendricks & Ross. The practice of writing lyrics to jazz solos, known as vocalese, is a geeky fringe of an already geekily fringe music. But for me it has a lot of creative value beyond its hipsterish metacommentary. Artists like Lambert, Hendricks & Ross have been crucial to my deeper understanding of jazz. If you want to learn jazz improvisation, the best method is to memorize solos. It’s a heck of a lot easier to memorize them if someone writes lyrics. If the lyrics are witty and clever, like Jon Hendricks’ are, so much the better, since learning solos becomes a fun word game in addition to an act of musical scholarship.

I hear a strong connection between the virtuoso wordplay of vocalese and contemporary hip-hop. I don’t know how many hip-hop MCs were inspired by vocalese. Queen Latifah cites about “Moody’s Mood” as an influence. I assume there must be others. I know that some of the best MCs have jazz training. Rakim Allah talks about having studied jazz saxophone, which you can hear clearly in his phrasing. Vocalese certainly did a lot to steer my attention toward hip-hop. I love traditional jazz vocalists, but the material they have to work with is increasingly dated and lame. Vocalese is more hip and challenging, but it still tends towards the slang and cultural references of the fifties. Hip-hop might not have the melodic and harmonic intricacies of vocalese, but the rhythms and internal rhymes are of a piece, and hip-hop speaks more to the world I live in. I’m hoping that as time goes on, hip-hop and vocalese will converge, and we’ll have our own generation’s equivalent of “Moody’s Mood.” Let’s get to work on that, my fellow musicians.

At various points in my quest, I thought I had identified some truly authentic musical forms and styles. Here they are, more or less in order of my embracing them.

Sixties Motown

When I was growing up, my mom and stepfather had the Big Chill soundtrack in heavy rotation. You could equate authenticity with soul, and there’s plenty of soul here.

In the eighties, my parents’ friends liked to praise the classic Marvin Gaye and Aretha Franklin recordings on this soundtrack as “pure,” by contrast to the music of the then-present: hip-hop, synth-heavy pop, Michael Jackson. I dutifully accepted this formulation, even though my ears told me to like the eighties stuff as much as the sixties stuff. I can’t argue with the musical qualities of the Big Chill tracks. The singing is full of emotional truth-telling. That said, the arrangements sound cynical and commercial to my ears now. All those strings weren’t exactly sticking it sonically to the man. The slickness of Motown drove me to eventually seek out…

Delta blues

Raw, intense, minimalist, tied to a specific time and place: this is as good a definition of musical authenticity as you could ask for. The fact that it’s being made by oppressed people is even better. I embody the cliched story of the white hipster going back through the Stones and Zeppelin and hearing all the music they were inspired by/stole from.

The blues is a powerful and truth-telling musical form. But my desire to participate in it quickly became a problem. Blues might have been authentic for Howlin’ Wolf, but for me, it’s an awkward fit. It’s not for lack of trying; I play the best white blues harmonica of anyone I know. The phrasing and microtones and general attitude have shaped my approach to every other style of music I’ve attempted. But if I was going to tell my own truth in music, I needed to find something socially a little closer to home. Jerry Garcia helpfully steered me towards…

Bluegrass

As the fans like to say, bluegrass is sung from the heart through the nose. It has all the earmarks of regional authenticity, including an apparent lack of concern with finding a wide audience.

As with blues, I ran up against some immediate cultural tourism issues when I started exploring this music. It’s easy for a New Yorker like me to condescend unintentionally, treating bluegrass as “pure” because its practitioners are supposedly unsophisticated hicks, and therefore “unspoiled.” The true story is more complicated. The bluegrass guys might be rural, but they most assuredly are not dumb. Bill Monroe conceived bluegrass partially on a commercial basis, choosing repertoire and instruments that appealed to the audiences of his time and place. Also, bluegrass requires a lot of technical skill, especially for the lead instruments like banjo and fiddle. It’s not a good genre for the casual dabbler. Besides, by the time I dug into this music I was also starting to get interested in…

Monk and Coltrane

One way to define authenticity is through exclusivity. Bluegrass excludes casual dabblers with its technical demands. But bluegrass isn’t remotely as demanding as bebop. This is part of the reason why bebop is as untainted by commercial success as any snobby hipster could wish. Hard jazz is consistently the worst-selling genre in America, year in and year out.

Monk and Coltrane don’t fit into the bebop box exactly, even though they helped define its sound. They’re good avatars of purity because of the extreme individualism of their respective sounds. Any three-second sample of either of them is instantly recognizable. Monk isn’t as impenetrable as his reputation would suggest — several of his tunes have melodies a normal person could whistle. Coltrane wrote some nicely approachable tunes too, but he gets extra authenticity points for spending his last few years playing harshly avant-garde experimental music.

I’d recommend that any musician tackle bebop if they want a rigorous education in American music generally. It’s all in there: the blues, the showtunes, the highbrow and the lowbrow, all the chords and scales and rhythms and textures our culture has to offer, at least up until the advent of electronic music. But much as I love it, bebop never really felt like home to me. I’ll continue to study Monk and Trane and their cohorts, and will continue to enjoy and be inspired by them, but if I want to express my experience in the present reality, they don’t have all the answers I need.

Klezmer

Okay, so if urban black or rural white music is an awkward fit for a New York Jew, how about the music of the tribe? Klezmer is culturally close to home for me. It straddles the shtetl and the big city, the old country and the new one, ancient folk forms and American pop.

Klezmer sometimes gets called “Jewish jazz” but a better comparison is to country. There’s the oompah-derived boom-chick beat, the harmonic minimalism, the melodic improvisation, and the emphasis on rawness and feeling over technical complexity. The scales are different — you don’t get a lot of Ahava Raba scale in country. But the comparison is close otherwise. Discovering this music was a key puzzle piece for me; I use those Arabic scales any chance I get. Klezmer’s mutt-like fusion of disparate styles is a truer statement of myself than anything that could be described as pure. Unfortunately, klezmer isn’t a great way to connect with other people aside from other NYC hipsters with Jewish ancestry, so it was never going to be my ultimate destination. But I’m glad to have gotten acquainted.

The impenetrable avant-garde

You could define authenticity as an uncompromising commitment to inner truth, the desire to please others be damned. There’s something noble and admirable in this commitment. The problem is that the furthest reaches of inner space don’t usually produce music that other people can connect to. I never enjoyed extremely experimental music, but the academic world and critical establishment hold it in high regard. As an educated highbrow type, I felt like I had to dutifully subject myself to a lot of avant-garde experiments in an effort to purge myself of my weak-minded desire for music to be fun. I guess I learned a few things about the limits of human tolerance, but mostly I learned that I really do just want to have fun. Here’s a hilarious quote from “Can Machine-Made Music Sing Without a Composer?” in New York Magazine:

[O]n February 5, the Fireworks Ensemble will perform a live version of Lou Reed’s notorious 1975 album Metal Machine Music, at Miller Theatre. Listening to Reed’s original double LP is a test of endurance. In his garment-district loft, he leaned various electric guitars against their amps so that they howled at each other in crescendoing feedback loops, and welded the tracks into deafening industrial polyphony. The result was one of the most loathed records ever to hit the market. Nevertheless, the intrepid composer Ulrich Krieger decided to arrange it for traditional instruments, an undertaking that smacks of flagellant zeal.

I like the word “flagellant.” We just can’t shake our puritan roots, can we? There’s a lingering notion that painful music has the deepest purity. I’m grateful to have rid myself of this silly idea. Deliberately annoying music seems to me now to just be another form of class competition, its flamboyant uselessness a bigger statement of materialist affectation than any crassly commercial pop.

Fake is the new real

So where has the authenticity quest ultimately led me? As a kid I loved Michael Jackson and Run-DMC to pieces, but as I got a “music education,” I felt morally obligated to reject their music for their sinful use of drum machines, synthesizers and borrowing other people’s ideas. Most especially, I felt I had to reject them for their emphasis on pleasing people above all other musical concerns. Now pleasing people seems to me to be the only good reason to make music. If “fake” and accessible sounds like synths and drum machines put bodies on the dance floor, then fake is better than real.

I’ve had an instinctive attraction to electronic music dating back to loving science fiction sound effects and scores as a kid. But my peers and educators pressured me to be suspicious and hostile towards high-tech, pop-friendly musicians like Herbie Hancock. Herbie’s acoustic piano work is acceptable to the guardians of the jazz canon, but controversy continues to roil over his embrace of the synthesizer, sequencer and the sounds on the radio.

I’m glad to have withdrawn from the battle over purity. Not everything you hear in clubs or parties is terrific, but rejecting it wholesale was getting me nowhere. Giving myself permission to enjoy pop-jazz fusion, Herbie’s seventies and eighties future sounds, hip-hop and dance music has opened up huge new continents of sonic enjoyment to me. Authenticity is about truth-telling. For a high-tech city dweller, loop-based electronic sounds are more truthful to my experience than banjos and mandolins. I’ve whole-heartedly embraced the whole bag of technological tricks: Auto-Tune, lip-synching, whatever you’ve got.

Musical authenticity is in the emotional content, not the tools used to make it. Many musicians of my acquaintance fetishize vintage gear. There’s the hope that if you play the same harmonica as Little Walter Jacobs through the same mic and the same amp, maybe some of that Little Walter Jacobs magic will rub off on you. No doubt, quality gear sounds good in the right hands. But the hands are more important than the gear. Good tools can make it easier to realize an idea, and can even spark ideas. But a lame, unpracticed or anxious harmonica player will sound lame, unpracticed or anxious no matter what. And there’s nothing inherently soulful or un-soulful about any instrument. Drum machines only sound inauthentic when they emulate human drummers. Drum machines are perfectly authentic when used for their uniquely posthuman quality. It all depends on the musician. Like Herbie Hancock says, the machine doesn’t program itself.

As of this moment, my favorite song is “Empire State Of Mind” by Jay-Z and Alicia Keys.

Is it authentic? Not really. It panders to me on many levels, as a hip-hop head, an R&B fan and a patriotic New Yorker. But Jay and Alicia pander so well, the beat is so tight, the chord progression and melody are so energizing, who cares?

The concern over purity is really about exclusivity. A mutt like me is is no position to be excluding anyone. But then, no one really is in a position to be excluding anyone. The shocking truth of biological evolution is that if you go back far enough, we’re all cousins with each other, and if you go back further, we’re cousins with bats, bananas, and bacteria. I believe strongly that the rules of evolution apply to music too. Our music all descends from the same monkey calls, so who’s in a position to be disputing the musical methods of anyone else? You don’t have to like everything, but disliking something is no reason to call its basic validity into question.