_I stuck with a predictable clique of jazz music for a while, when I was younger—John Coltrane, Miles Davis, Thelonious Monk—then sought out less obvious talent. I backed up toward Ellington and Armstrong and Charlie Parker, but always remained fixed to the idea that transcendence in jazz ultimately depended on some degree of moody seriousness. An easy mistake, and lately I’ve taken small, important steps to correct it. I’ve shifted depths; my range of apprecia­tion has improved. For this Bob Dorough is largely responsible. His byzantine career is exhaust­ing to dig through. Finding his records takes work. But after considerable searching, and playing his songs, and cross-referencing, and patience, and ultimately cracking open the frigid attitude by which I considered his music an “acquired taste”—the flimsy compliment he’s been accorded by crit­ics to describe the strange wit of his songs—and simply after listening, without prejudice, to his music, I’ve eased into a fold wherein lies a delightful problem: Cursed with obscurity, Bob Dorough might nonetheless be a genius. Obscurity precedes him as a jazzman; as Americana, as pop cul­ture, he’s more familiar to us, since he’s the musical wizard behind the Saturday-morning jams known as Schoolhouse Rock!', a gig that provided rewarding, lucrative work, but which also meant that his fan club, if he’d had one officially, would have mostly consisted of milk-spilling, pretzel­-legged children splayed out on floors not five feet from the television, inadvertently mesmerized by his lysergic boogies on multiplication and the parts of speech. Who didn’t really collect jazz records. But who would, many of them, a generation later, recognize his voice while waiting on tables in a club where he’d be working through his repertoire, and would ask him...and affectionately request...until eventually the Schoolhouse Rock! stuff got mixed in with the jazz stuff, and Dorough would end up using rock as a “proselytization of jazz,” which to some degree has been working, since that is exactly how he piqued my interest and eventually led me to a kind of jazz enlightenment. All of this, of course, relies on a kind of cultural accident, just because an ad executive wants his kid to learn the multiplication tables by putting them to music, and he happens to meet a jazzman who can do it, so that in 1973 television history gets tweaked a little bit, and the jazzman’s career gets tweaked a lot.

_He started out with bebop ambitions, in 1949, traveling by bus from Texas to New York with books and records as his only pos­sessions. He waded through New York’s jazz culture by way of small gigs on Manhattan’s West Side, or in Brooklyn, or Queens, wher­ever they needed a piano player who could sing. He led a double life of sorts, obliging the East Side crowds with jazz standards— pleasant numbers like “Basie Blues” and Hoagy Carmichael’s “Up a Lazy River” (songs he loved)—then jamming fanatically with other beboppers after hours.

He scurried among the clubs on 52nd Street—the Three Deuces, the Downbeat, the Onyx—seeking Charlie Parker out. He’d find him regularly at Birdland, or follow him to ballrooms. He showed up at a high-school prom just to see him.

In the liner notes to a reissue of his first album, Devil May Care, Dorough writes lov­ingly and with hepcat enthusiasm about the thunderbolt Parker was to him:

Oh, it was crazy how we dug Bird. We'd give up pork chops for beans to have cab fare and admission to Birdland (cheep). We'd follow him whenever we could, session-gig-or-concert.... We loved every note he played. We loved the squeaks of his reed. We dug other people too, especially the giants and the survivors, Diz, Miles, Thelonious...but we really dug Bird...it was like idolatry...it was crazy...we were Bird-happy, Bird-struck and Bird­-bent...and mostly, tryin' to learn to blow a little.

Occasionally Parker would grace jam ses­sions at a basement apartment in the William Henry Hotel. There would always be one bass, one piano, one drum kit, and about fifty musi­cians sweating and smitten and pressing for a chance to play. Who knows how they lured Parker into it; promised him junk, no doubt. As for Dorough, he rarely ever got there early enough to sit in; usually he’d listen at the edge of the room. But on one night, when Dorough heard that Parker would be there, he rushed down in time for a good slot, and squeezed in among the piano players packed like gamblers around a hot hand at a craps table, listening to Parker flit through about twelve chorus­es of “(Back Home Again in) Indiana.” When it was over, with tense politesse the standing players requested turns, and Dorough leaned into the piano player’s ear and asked him: “Okay, man, you played a tune, now let me have one.”

Lips on the reed, eyes to the side, Parker unfolded the melody for the next song, and the new sidemen fell in, Dorough among them. He would recount this night for friends who couldn’t make it, share it proudly with his wife. The moment put a fire to his jazzman ambitions.

Months later, as luck would have it, he and Parker shared a stage. Buddy Jones, a mutual friend who often shuttled Parker around the city, showed up at Dorough’s East Side cold-water flat one evening to see if he was booked.

No, nothing.

Then get your hat and coat, Jones told him. Bird needed a rhythm section and had asked Jones to put one together. Bob would be the piano man, that simple. (“My spine went icy cold,” he says.) The gig was in Queens some­ where, a nondescript bar, but word got around and the place filled up. Dorough remembers Bird arriving in a cast up to his thigh. They sat him down and propped his leg up on a chair. The piano was an upright; Dorough faced the wall. Parker sat to his left. There wasn’t much small talk. The songs were standards, no pressure. When Bird played the first few notes of “Besame Mucho,” the drummer knew it was a rhumba. Dorough got there by the sec­ond chord, and the bass player followed. But why the cast? Dorough never asked him. “How could you?” he says, still awestruck. “How would you?”

_Charlie Parker's death in 1955 was especially painful to jazz musicians in New York, where the music was such an intimate art, its players separated by just a few degrees. Hearing and walking among and—if you were lucky—playing with flesh-and-blood giants like Parker created a musical zeitgeist that was badly weakened by Parker’s death.

Dorough had recently returned from Paris when it hap­pened. By then he had developed a singing style that drew from vocalese impresarios like Annie Ross, Eddie Jefferson, and King Pleasure, and was able to layer his various admira­tions—for the American songbook, for bebop and its off­-shoots—into one persona. As a tribute, he worked out a vocalese rendition of Parker’s “Yardbird Suite,” tacking lyrics to the horn’s part. “I’d stand, waiting for a train or bus,” he wrote, “vacant-eyed, staring, trying to make the lyrics fit the brilliant solo he’d recorded on Dial Records and which I’d first memorized. I didn’t think he’d care if I had to stretch it here and there.”

The song thrust his hyperactive, hyper-inflected, acrobatic Southern lilt at beboppers, traditionalists, and everyone else in the way. By giving his consonants unusual elbow room and letting syllables fall like a tall house of cards after Parker’s lead—“Whenhehad themiserablewoes / He seemed to pull-out-his-horn / And make each person lis-ten / Andfeelthathe’d never-known what bein’ low down could be”—Dorough flashed a personality in place of whatever groomed savvy a crooner might have projected.

“Yardbird Suite” was a highlight of Devil May Care (1956), a strange, romantic, infectious record guided by a gamboling voice. His singing style on that record—and throughout his career—projects an unguarded joy, even on his melancholy rendition of Hoagy Carmichael’s “Baltimore Oriole,” as smooth and gray a version as Carmichael him­self could have whispered.

The record flopped, and the jazz press was only lukewarm to it. (Over the years, it’s been said that he sounds like “Nat King Cole impersonating Louis Armstrong” or “a high-pitched King Pleasure.”) But Devil earned Dorough a cult sta­tus among fellow hoppers and hardcore listeners. Mort Fega, the legendary host of WEVD’s Jazz Unlimited, out of New York, was immediately hooked. “I became enamored of his style,” he told NPR’s Jazz Profiles in 1998, “and played the record generously. I created a lot of interest in it—as much interest that could be generated with the kind of performer Bob is. He doesn’t have a broad appeal. Actually, he’s too hip to have a broad appeal. His following to this day is very much a selective minority appeal.”

Fega would often play Dorough during the “Best Kept Secrets” portion of his radio show, and eventually would sign him to the short-lived Focus label, which released Bob’s sec­ond album, Just About Everything, in 1966. That record fea­tures a gnarlier voice, unafraid to swing lower than it did on Devil, slightly harder than the wispy thin-legged one his fans already knew. (He’d taken voice lessons while acting in a St. Louis production of A Walk on the Wild Side, and had learned how to project.) His style was bolder—and it would grow bolder still across a dozen albums—nasal, hyper-articu­late, clutching a line longer than comfortable, hogging the ball, but always romantic in tone. Just About Everything includes some sneaking through other genres, too, including a ragtime uptempo cover of Bob Dylan’s “Don’t Think Twice, It’s All Right,” which, by its wily style and stubbornness, makes Dorough cousin to Dylan, or at least a kindred spirit.

By the time Dorough recorded for Focus, he’d been in the music business long enough that, according to Fega, “he had a wealth of experience as a record producer. There was no ner­vousness about what he did in the studio. He was like in his mother’s arms. Very comfortable. It went down like milk and honey. It was easy.”

Just About Everything turned out to be one of Fega’s favorite projects, but failed to sell. In fact, none of Dorough’s albums, published mostly on small if not his own household labels, would do much better than Devil May Care. But his cult status would hold steady, and in the meantime he’d gig relentlessly, meandering like a Zelig through music: writing commercial jingles, producing a pair of albums for Spanky & Our Gang (which included the chart hits “Sunday Mornin’” and “Like to Get to Know You”), and working with the oddball counterculture noisemakers the Fugs (which led Allen Ginsberg to hire him to play piano and organ for a musical interpretation of William Blake’s Songs of Innocence and Experience). He’d write songs popu­larized by others—“Comin’ Home Baby” (written with his longtime bassist Ben Tucker), which became a Mel Torme standard; “Devil May Care,” “Nothing Like You,” and “Love Came on Stealthy Fingers” by several artists—and songs others would ruin (“I’ve Got Just About Everything” by Tony Bennett). He would make a record of Lawrence Ferlinghetti poems set to jazz (Jazz Canto, Vol. 1) and share a billing with Lord Buckley, the beatnik performance artist who recited hipster renditions of Shakespeare monologues. Lenny Bruce would hire him to play accompaniment for A Sick Evening with Lenny Bruce. (“When the intermission’s almost over,” he’d instruct Dorough, “go in and play a few of your shticks. Get ’em back in.”) Then Schoolhouse Rock! would make his voice famous.

The tight but loyal following would grow, slowly. He signed with Blue Note in 1997, his first major-label contract, and that resulted in three releases—Right on My Way Home (1997), Too Much Coffee Man (2000), and the live album Who’s on First (2000) with Dave Frishberg, the dry doppel­ganger to Bob’s nerdy showmanship, with whom he wrote the popular “I’m Hip,” a tune saturated with a wry self-awareness: “Well I’m dig / I’m in step / When it was hip to be hep / I was hep”; “I even call my girlfriend ‘man’ ”; “Bobby Dylan—he knows my friend!”

My favorite album of that trio, and a nice bookend to Devil May Care, is Too Much Coffee Man (sans comma because it’s a moniker). By the time it was released, Dorough had collected mostly guarded compliments from critics; but by snooping through blogs, talking with people who’ve heard him, and reading the feedback of customers who bought Too Much Coffee Man on Amazon.com (as I did), I got a clear sense of what the critics had missed, what’s so uncanny about this jazzman’s audience: With Dorough fans, appreciation gets slapped aside by passion. The hyperbole of those who bought that record proves it: “He has no equal,” wrote one buyer. “He is jazz, he is piano, he is mood, he is a poet in disguise”; “This is an example of the reason American music is great: startling creativity”; “Thanks for the great gift of yourself, Bob”; “Get this...and listen to it 10 times. You’ll be hooked... Whatever you do, thank your personal god that this man is alive and well and still making important American music.”

Unfortunately, such passion wasn’t enough to sustain his run with Blue Note. Since 2000, he’s recorded three albums, but on much smaller labels, including his own DeesBees Records. “If corporate strictures weren’t what they were now,” says Tom Evered, the man who brought Dorough to Blue Note, and who is himself a devoted fan, “I would gladly make another one with him. But it’s hard to get airplay. It’s hard to get expo­sure. It’s difficult to get a record like that out to the public.”

Any of the contemporaries Dorough’s been compared with—Mose Allison, King Pleasure, Randy Newman, Dave Frishberg—might be better singers technically, or better musicians technically, but none seem to trigger the same fever in ordinary people. And understand that Dorough’s humor has a bottom under it: Though he may not win acco­lades for a dazzling technique, his music is unquestionably sophisticated, with a gifted touch for arrangement. So how does a jazzman inspire such admiration from his peers, and such rock-star devotion from his fans, and still hunker at the respectable but dimmer status of cabaret singers? The safe answer, of course, is that he’s an acquired taste.

_Born in Cherry Hill, Arkansas, Dorough was eight when a his father took in a pair of vaudevillians passing through town. While staying with them, the duo prepared a routine for local schools, for which young Bob was recruited to sing such songs as “When Polly Was a Little Girl” and “My Blue Heaven.”

Music was a family talent. Dorough’s father played hymns on whatever organ he could find; his uncle favored cowboy songs on the guitar. Bob took a total of six piano lessons, then noodled around on his own, learning to play by ear. Later, violin lessons were a trial: “Just twenty kids playing ‘My Country ’Tis of Thee'—all the same notes.”

When the Doroughs moved to Plainview, Texas, Bob joined the high-school band and became a protégé of the band director, who taught him the principles of harmony, how to play the clarinet, and how to conduct. He found his groove in the dynamics of the ensemble. “Just sitting there and hearing the other kids playing different instruments,” he says. “How it all fit together, and realizing that the part I played was impor­tant to the whole texture.”

The Army drafted him in 1943, interrupting his studies in composition at Texas Tech University. He drifted through a few stateside bases with different Army bands, playing saxo­phone, more clarinet, and piano. He learned Nat King Cole, Louis Armstrong, Jack Teagarden, Hoagy Carmichael. He wound up in Hot Springs, Arkansas, while it served as an ersatz rehabilitation village, where he played afternoon “tea dances” for veterans returning from overseas. He met his first wife, who moved with him to Amarillo at the end of his service, the duration of which—two years, nine months, and twenty-seven days—he’s quick to rattle off.

In Amarillo, he began showing up at the Aviatrix, a club where several military musicians would reunite to play the big-band crowd pleasers that filled the nightly billing. Dorough met a pair of Air Force horn blowers who invited him over to listen to Dizzy Gillespie’s “Hot House” and “Groovin’ High,” as well as Charlie Parker’s “Ornithology.”

At first, the songs befuddled him. So they explained it—how “Hot House” was just a variation of “What Is This Thing Called Love?”; how “Groovin’ High” came from “Whispering”; how “Ornithology” mirrored “How High the Moon.” They played these songs over and over, distilling and decoding the phrasing. “They gave me the keys to the kingdom,” he says, “in one simple session.”

What clicked? Reflecting on it, he recognizes a genealogy: “As a student of composition, and of music in general,” he says, “I had to know everything there was to know, if I could learn it. And, you know, bebop was highly affected by European music, the harmonies of French guys like Debussy and Ravel, and the rhythms of some of the wild guys like Stravinksy. The music was borrowing these rich harmonies for jazz, so it was easy to admire this cross-pollination. So I dug in. And, sure, I was enamored of bebop partly because it was bizarre.”

He ordered dozens of records from DownBeat and wore them out on the turntable, all the while collecting letters from a friend who had moved to New York and gushed over what he’d been hearing in Harlem’s clubs. Being outside that hot circle was too much: He headed North.

_By 1952, Dorough was deep into what he calls his “lean period.” For three dollars an hour, he worked as a session pianist at Henry LeTang’s tap dance studio in Times Square. One after­noon, LeTang mentioned a five-dollar job in the main studio down the hall. Sugar Ray Robinson, retired from boxing, was putting together a variety show and needed a piano player. Henry introduced them, and said, “Play ‘Green Eyes’ for Sugar.” Dorough played it, and when he was done, Sugar Ray said curtly, “You’re going on the road with us.” And that’s all there was to it.

It was the beginning of a two-year gig as the show’s musical director. Robinson hated to fly, so the cast and crew traveled by train—hitting Montreal, Chicago, Vancouver, and Los Angeles. The retinue swelled along the way: hairdresser, manager, chauffeur, valet, the wife and child (sometimes), more hangers-on.

The show included a retired vaudevillian named Joe Scott, who played the funny man to Sugar Ray’s straight man, and a girl who sang in French, another who performed ballet, and several more who danced a can-can. It included a juggler and a handsome triple-threat ventriloquist, magician, and “pick­pocket extraordinary.”

The job put Dorough with heroic company. He played opposite Louis Armstrong in Chicago (“I watched every set he played. It was always the same repertoire, four times a day, but beautiful”), opposite Earl Hines in Providence. He wrote and arranged charts, some of which were played by Count Basie and his orchestra as the opening act, after which Dorough would take over Basie’s hot seat and lead the band.

With hubris, Sugar Ray took the show to Paris, traveling first-class across the Atlantic on the Île de France, bringing along his pink Cadillac convertible for good measure. Opening night, at the Olympia theater, the show bombed. It wouldn’t run long after that, but long enough, at least, to give Dorough the chance to snoop through the city’s jazz clubs, to hear what was happening and pick up extra gigs. He found one at the Mars Club, a popular cabaret on the Right Bank, where the owner, an expatriate named Ben Benjamin, sug­gested that if Dorough ever quit Sugar Ray, he could play the Mars on a regular basis and, more importantly, play whatever he liked. The names of its alumni were written on the door: Bobby Short, Annie Ross, Billie Holiday, Eartha Kitt, Kenny Clarke, among others.

When Sugar Ray announced, without ceremony, that the show had been cancelled and that they’d be returning state­side within a week, Dorough took Benjamin up on his offer. He began a five-month stretch playing seven nights a week at the Mars, developing a confidence in his style that had eluded him in New York, flexing the idiosyncrasies that felt so natu­ral to him. “Something crystallized in Paris,” he says. “I didn’t reach some kind of level until that gig, where I could experi­ment and write my own songs, where I was the boss and no one could gainsay. It was the first time I got to do what I wanted to do.”

He worked with Blossom Dearie, of the glass-menagerie voice (and who would later sing Schoolhouse Rock!'s “Figure Eight”), and recorded with her French vocal group, the Blue Stars of France. He befriended the journeymen piano players Aaron Bridgers (“an elegant expatriate”) and Art Simmons. He backed up Maya Angelou, on tour as a chorus member with Porgy and Bess, for her repertoire of calypso numbers.

Homesick, he sailed back on the Île de France second-class (which was still rather nice) and returned to New York in 1955, “thinking I was hot stuff.” He booked more nights in East Side rooms and was finally discovered by an agent, who signed him with Bethlehem Records. Devil May Care was released the next year, beginning its slow commercial burn. 

_E ven if Devil May Care sold well, it would have been difficult for Dorough to play regularly enough to build a fol­lowing. He’d been arrested in 1953 for marijuana possession, at a gig in New Jersey, and had had his cabaret license revoked, part of a campaign to clean up jazz clubs that dam­aged many musicians’ ability to play. Gigging thereafter was difficult at best, with his playing limited to one or two nights in small clubs just to avoid the attention of the Liquor Board. It was an exhausting way to nurture a record, never mind a following.

Meanwhile, Bethlehem Records was in trouble. Red Clyde, an A&R man who’d left Bethlehem to start Mode Records in Los Angeles, offered to record Dorough if he could make it out West.With Bethlehem spiraling and New York being so difficult to work in, there wasn’t much to mull over. By way of a gig in Tucson, Arizona, Dorough reached Los Angeles in 1958.

Bethlehem soon folded, and Mode never got off the ground. Dorough was stranded, with no label whatsoever, but free to play as much as he wanted. He began buying his own records wholesale from Bethlehem’s distributor (a buck a piece) and using them, as many jazzmen did, as calling cards for gigs. Whatever was left over he sold on the side.

He quickly plugged into L.A.’s jazz circuit, playing the Renaissance, the Twelfth Knight, George's Caprice, and fre­quenting the Hillcrest. “It was incredible, what was happen­ing there,” he says. He crossed paths with the wild talent of Paul Bley, Dave Pike, and Eric Dolphy. He turned around one night to find Ornette Coleman on stage with him. (“I heard this strange alto sound come in suddenly, cranked my neck around, and he was blowin’ this plastic horn. The sound was startling. It was blood curdling.”)

Miles Davis came to LA. with his sextet in 1959, settling in for an extended gig. While in town, Davis visited with Terry Morel, a friend he and Dorough had in common. One afternoon Davis noticed a copy of Devil May Care propped on Morel’s shelf and asked to hear it. The next day he asked to hear it again. Excited by his apparent interest, Dorough asked Morel to accompany him to one of Davis’s shows so they could meet.

They arrived to find Miles standing idly offstage while the rest of the band—John Coltrane, Cannonball Adderly, Wynton Kelly, Philly Joe Jones, Paul Chambers—kept play­ing. He and Dorough were quietly introduced, and, forego­ing cordialities, Davis took him gently by the wrist and whispered: “Bob, go up and sing ‘Baltimore Oriole.’ ” He  then led Dorough to the stage, cutting short the song and motioning for Coltrane, Adderly, and Kelly to step aside. Befuddled, all Dorough could do was look at Chambers and give him the song’s key. “I don’t remember much about it,” he says. “I just felt weird. It was a jazz job of the highest order, and I didn’t know what these guys were gonna think. I just said to Paul, ‘Well, it’s in F minor, just follow me.’ I didn’t know what to do but just sing it.” When it was over, the band took a break and gathered at the bar for drinks. By then Davis had disappeared.

That strange encounter led to a friendship of sorts. They’d attend the same parties, and if Miles saw a piano he’d pull Dorough aside and ask him to play. “That’s how I introduced him to ‘Nothing Like You,’ ” he says. “He was always getting me to sing something for him.” Dorough would open for Miles at the Village Vanguard once they reunited in New York. He would spend evenings at Miles’s home on 77th Street, listening to the rushes for Sketches of Spain, sprawled on the living-room floor, the casual intimacy of which he remembers as a “wondrous experience.”

One morning in the summer of 1962, Dorough got a call from Davis, who asked if he would write a Christmas song for an upcoming Columbia Records project. It was a quick call, mostly with Miles’s attorney, Harold Lovett. Dorough imme­diately began work on what would become “Blue Xmas,” a hard bop number in which he transposes his interpretation of a Miles Davis attitude into the lyrics, aiming for a “very Dickensian ‘Bah! Humbug!’ sentiment.”

They arranged the song with Gil Evans the night before recording, and even devoted some time to working on Dorough’s “Nothing Like You.” The musicians gathered at the studio the next day—Dorough, Willie Bobo, Wayne Shorter (his first time playing with Miles). Evans’s charts arrived by messenger. Miles was in the booth, tied up on the phone.

As Dorough wrote in his book on the experience, Blue Xmas, “everything was going pretty smoothly, in that I was with some friends for the purpose of making music.”

Then Dorough figured out what had been occupying Davis: He was desperate to find another piano player and had been calling around. Wynton Kelly was stuck in Philadelphia; Bill Evans was tied up with his own session. Writing about it later, Dorough recalls Miles driving in the dagger:

I kept saying to Miles, “I can play it, man,” and I was in place at the Steinway since nobody else was sitting there. That’s how I did my vocals—seated at the piano. Miles would say, “Lay out.” I had one delicious thought that I was being put in a class with Thelonious Monk. I’d once been present at Birdland when Miles kept turning to Monk say­ing, “Lay out.” This came to be known as a texture called “strolling,” where the horns and the bass and drums go with­out the piano chords.

I said, “Miles! These tunes are too hard! I gotta play to help me stay in key.” He’d say, “Just hit the first chord, Bob, then lay out.” So that’s how we did it.

The song required one take (afterwards, they moved on to “Nothing Like You,” on which Dorough sang but was again dis­couraged from playing). When all was said and done, he would walk away with a standard musician’s fee, with Davis listing himself first on the songwriting credits.

“We’ve all heard stories about Miles putting his own name on other cats’ tunes,” Dorough wrote. “To tell the truth, I stayed quiet about it and pretty much forgave him because of the mag­nitude of his talent.... My meeker, humble self rationalized that without Miles I wouldn’t have a track on Columbia Records at all.” And although Dorough actually owned copyrights to the song through the Library of Congress, “I just sat on the secret and let it ride.”

Miles and Dorough would remain acquaintances, but their relationship would be lopsided at best. Bob would sometimes stop by Miles’s home only to be turned away by a stranger; and on one occasion in the Village, Davis spotted Bob walking and flagged him down, but just to borrow twenty bucks (“Gotta see a man,” he told him). Years later, at a musicians’ hangout called Junior’s, Dorough discovered Davis’s rendition of “Devil May Care” on the jukebox. Miles had recorded the song just a couple of days after the “Blue Xmas” session, though Dorough never knew about it until he saw it on the Wurlitzer. He was shocked, but he was more bowled over by Gil Evans’s arrangement. “I used to sashay into the bar...and go right up to the box with a quarter in my hand before ordering a beer.... I spent a lot of quarters on that.” Davis would tip his hat again, in his own way, when “Nothing Like You” wound up on his 1967 record Sorcerer—a. wispy, vocalese-bop intrusion on this otherwise atmospheric windup, its only connection being Evans’s pianoless arrangement, its horn and bongo backbone. “I was dumbfound­ed,” says Dorough. “Miles just dropped it in. Maybe he needed three more minutes, I don’t know.” Dorough would get royalties, but by then his relationship with Miles was all but dead.

Songs aside, Miles didn’t do Dorough any favors with his brief mention of the “Blue Xmas” session in his autobiography, which amounts to a dismissal: “Then Columbia got the bright idea of making an album for Christmas, and they thought it would be hip if I had this silly singer named Bob Dorough on the album, with Gil arranging.... The less said about it, the better....”

_Miles Davis may be his own revisionist, but his dismissal cuts to the quick of Dorough’s curious struggle as a jazz artist, which in turn leads to the curious issue of jazz’s cult of high seriousness, the door through which most people first enter jazz.

The players who first guided my own fascination with jazz— Coltrane and Davis especially—were of that cult, masters of bebop’s musical puzzle and arbiters of its detached cool. Charlie Parker was, in a sense, a transitional figure, a sanctified hunger­ artist who suffered famously but played with an untouchably pretty style and obvious wit. It’s hard to say whether his vices handicapped his music, but it’s clear that his sad backstory cre­ated an irresistible irony to how lovely that music was.

But to the extent that Parker introduced a bright complexity in jazz, so many of the trailblazing jazzmen who followed drew the music out to such depths of humorlessness that it remains stuck there. Coltrane, with his blitzkrieg solos, offered no musi­cal levity to his addictions and suffering the way Parker did. No matter how brilliant, his sound is infused with moaning, low or high, always laced with the tragic. Davis, with his freaky, esoteric discipline and Prince of Darkness persona, flatly rejected ingra­tiating himself with an audience. Ornette Coleman, meanwhile, played with such abstract intensity that his music sometimes resembled a thesis.

To a greenhorn like myself, modern jazz is appealing for obvi­ous reasons, not the least of which is the chance to bear witness to such profound talent. But jazz also appeals for many of the same reasons that a band like the Replacements did when I was younger: The music is mood-driven, often introspective, speaks of suffering with beautiful flourishes. The rub is that jazz, by virtue of its difficulty, is exclusionary, a quality reinforced by the attitude of seriousness.

Dorough, of course, knows this peculiar form of exclusion— bebop’s inner-sanctum politics—because he was there in the thick of it. Decoding the obtuse was a form of initiation. “It was supposed to be a revolutionary music,” he says, “and its creators were trying to obfuscate the scene a little bit. They didn’t want you to dig ’em. They say around Minton’s Playhouse, where a lot of the fomenting took place, they had secrets, like knowing that ‘Hot House’ was really ‘What Is This Thing Called Love?’ but unless you were an exceptional musician you wouldn’t know what the hell they were playing. And you’d take your horn and sit down because you didn’t understand it. So they were weeding out the lesser lights. It was a cutting session. We as students of the music, we were doing our best to be in on the secret. It was esoteric stuff, there was no doubt about it.”

And while high seriousness developed naturally out of such complicated music, the posture of cool matured for a new pur­pose—mainly, the shirking of the traditional entertainer’s role. Coolness on stage was a form of dignity, which young black players demanded not only through their technique, but also through their stage presence. Being funny, being lighthearted, being cordial all risked smacking of Stepin Fetchit.

That’s a familiar line in jazz’s sand: art vs. entertainment. It’s a line that traces back to Louis Armstrong and his use of humor as a form of supplication. Beboppers rejected him for that easi­ness in his personality, the grin, his implicitly self-deprecating sense of humor, which they tagged to minstrelsy. But, as Ralph Ellison clarified when he wrote about this division in 1962, to dismiss Armstrong was to confuse politics with artistry.

“Louis always remained a consummate entertainer,” Dorough says. “But it’s true: Since his time, if you become a singer, it’s different. It’s commercial, it’s troubadorish, it’s clownish. That’s why the beboppers wouldn’t announce tunes or say anything to the audience. It was a political thing. So they’d just go on the stand and they’d nod at each other and go dulitlitulitididididuh—and when it was over they’d do another one. I’m a different kind of personality. I’ve just always felt that if I had a job, I had to say, ‘Good evening.’ ”

So Dorough chats, introduces songs, tells a funny anecdote, hams it up. But does that mean that he lacks seriousness? In a narrow sense, yes. But he also exudes the tragic potential of the comedian, the offbeat wisdom of a trickster. I’d risk, too, that he often reflects the “crazy wisdom” of the Eastern holy fools. Tom Robbins, writing about the dour literature venerated by Western intellectuals, suggests that crazy wisdom might be an antidote to the “toxic contagions of sordid fiction” he finds so depressing. He refers to those Tibetan mystics for whom folly and humor have as much spiritual potential as any Catholic tradition, who use play­fulness to kick apart the wooden strictures of conformity, clearing paths to enlightenment through a “wisdom that turns the tables on neurosis by lampooning it”—which, through a deceptively breezy approach to love and suffering, Dorough does.

Much of his holy-fool effect relies on his voice. It flits and sidewinds through a ballad, but then dips into drunk­-tank sourness in a song like “Small Day Tomorrow,” drag­ging the preposition (tah-maah-wrowww) like he’s having a slow-motion tantrum.

The voice, in turn, prods the lyrics, reams of which were writ­ten by Fran Landesman, whom Dorough met while acting in St. Louis. Through dozens of songs, her hipster sentimentality jux­taposes elegantly with Dorough's glib delivery. Sentiments like “Yes, you showed me all the colors of the rainbow / But I didn’t know the price I’d pay / Have mercy on me, babe...” are trailed by something that wavers between a raspy croon and a yodel.

So really, the problem isn’t that Dorough is inappropriately funny, or even silly. He’s strange, sublimely so. Unintelligibility is easy to defend against, but strange gets under your skin. And artistic strangeness is rather difficult to achieve. In this case, being a jazz artist, it relies on musical prowess without taking the sentiment too seriously. The juxtaposition, when it works, works beautifully, as it does in “Whatever Happened to Love Songs?” The line I’m thinking of seems innocuous enough: “No magic left in the music / Now that my lover has gone.” Reading it, you’d never guess how Dorough stretches that last vowel toward a high “A” just shy of the pitch. It is the opposite of crooning. It would make a balladeer wince. But it is lovely here—uncomfortable, intelligent. Granted, his style suits the giddy dangers of falling in love better than heartbreak’s darker fallout; but no one does giddiness like this.

_The story is that David McCall, a New York advertising executive, was at the end of his wits: His son simply could not grasp the multiplication tables, but knew every Rolling Stones lyric cold. McCall figured that if he could set the multi­plication tables to rock, his boy would finally get it. He would fund the whole thing—costly, yes, but he was desperate.

He and his creative director, George Newall, auditioned dozens of Broadway songwriters. Newall, meanwhile, was going through a divorce and spending a lot of time at the Hickory House, listening to and hanging out with jazzmen he met there. He befriended the bassist Ben Tucker, who imme­diately recommended Dorough for the project. Newall had never heard of Dorough, but he was game.

“The other musicians all came up with something very sim­ple,” says Dorough, “you know, doggerel poetry and simple rhythms and melodies, as though children couldn’t handle it. I thought he was going to give me a high-price jingle to write. But then he said, ‘But don’t write down.' That sent chills up my spine.” Dorough left the meeting somewhat terrified, but thrilled. “Here was a chance to communicate with children— who didn’t want simple stuff, who wanted something.” He pored through books left over from a college course, studied for weeks before writing a single note. “I wanted to put the multiplication later,” he says, “and first tell them something about the Trinity, the triangle. I dug up things from the Bible and philosophy. And I was a fan of Buckminster Fuller, who said, simply, that the triangle is stronger than the square or the rectangle, because you can’t push a triangle over. It sup­ports itself; there’s nowhere to go.”

“Three Is a Magic Number” was the result, the first song Dorough submitted for McCall’s Multiplication Rock project. Ironically, it was never intended for television; it was only supposed to be a record. But it just so happened that Tom Yohe, the agency’s art director, was in the room when McCall played the tape; he started sketching out what images the lyrics triggered. Those sketches evolved into a storyboard, and soon enough bulbs went off and wheels started spinning  and both the song and storyboard were presented to McCall’s biggest client, ABC. The network bought the project and commissioned the rest of Multiplication Rock, which included the songs “Three Is a Magic Number,” “Figure Eight,” and “My Hero, Zero.” The group then tackled the eight parts of speech through Grammar Rock, which includ­ed trumpeter Jack Sheldon singing “Conjunction Junction.” Dorough put his touch on all of it, songs about science and history and civics. The show would be cancelled in 1985, but by then would have already imprinted in a million minds the basic lessons of education’s three Rs through a simple musi­cal principle—repetition. And, to boot, the songs easily hold their own against any of that era’s pop music.

Dorough had no idea if the show was successful; it wasn’t anything you could measure in sales. “I didn’t know if any­body else was watching it,” he says. “So I volunteered to do assembly programs. I took the Manhattan Yellow Pages and booked about ten recitals. I’d say, ‘This is Bob Dorough. I’m with ABC Television and Schoolhouse Rock! We have a Christmas present for the kids....’ ABC had nothing to do with it. I booked all these concerts myself. All I needed was a piano and a mic. I’d arrive at the school and the principal would say, ‘Well, we never heard of you, but the kids seem excited.’ And after getting up on stage, I’d go into ‘Three Is a Magic Number,’ and I would look out and see the kids. They’d be nudging each other: ‘It’s him.'

“Then I knew.”

_I saw Bob Dorough perform a few times before I got to know him, most recently in the sleepy lake town of Heber Springs, Arkansas, at a chamber music festival. His daughter, Aralee, is principal flutist with the Houston Symphony Orchestra, and had recently recorded an album with him, The Houston Branch. She’d been invited to Heber Springs to play chamber music and mentioned that her father was born in Arkansas, which inspired the festival organizers to invite him down as part of Arkansas Heritage Month. (He’d already been inducted into the Arkansas Jazz Hall of Fame.)

The turnout for his show was small, about twenty-five people. The intimacy worked and it didn’t; the lo-fi dynamics were an injury. A good deal of Dorough’s performance depends on the way his singing barges in on, ribs, and kneels before the music. Running his voice through what sounded like a tube amp made things a little rough.

But what the show lacked in hi-fi was overshadowed by intelligence. Dorough minded this classical context: New arrangements of his bebop songs were followed by a modern, contrapuntal duet for flute and oboe (featuring Aralee and her husband), followed by a piano/flute duet of “Yesterday” (an arrangement he’d written for Aralee as a child), and then an abstract version of “All the Things You Are.” The songs were threaded together by the flute’s touches. This was, after all, his daughter’s occasion.

The second set opened with the Schoolhouse Rock! stuff (it usually does), and I got that slight nostalgic rush. So did the soundman, who was so moved he hooted. This material was really all I knew of Dorough’s music then; seeing him perform it twice now, introduced the same way, as a singalong, and hearing a timid audience tip-toe through the multiplication bridge in “Three Is a Magic Number,” I realized that he might actually be sick of having to work these songs into his set. So the nostalgia vanished, though I did my best to shout the numbers out. We met up the next day, rising early. He seemed doleful—chuckling, and sweet, but also understated and careful. I ordered eggs. He ordered pancakes, said to the waitress: “but done, you know what I mean? And a side of bacon, just for atmosphere.”

We talked about Sugar Ray and Los Angeles; he introduced me to a couple of theories on harmony. Thinking back on it now, his demeanor, I’m reminded of what Ellison wrote about Armstrong and the hard boppers:

Certain older jazzmen possessed a clearer idea of the divi­sion between their identities as performers and as private individuals. Offstage and while playing in ensemble, they carried themselves like college professors or high church dea­cons; when soloing they donned the comic mask and went into frenzied pantomimes of hotness—even when playing “cool”—and when done, dropped the mask and returned to their chairs with dignity. Perhaps they realized that what­ever his style, the performing artist remains an entertainer, even as Heifetz, Rubinstein or young Glenn Gould.

We talked about Schoolhouse Rock!, of course, and I asked him if he ever tired of playing it. “I’d be a poor musician if it wasn’t for Schoolhouse and a few other songs,” he said. “Theoretically, I make enough money to live on. I could just go to the mailbox every week. But I troubadour because I love to perform. And I’m a ham. I just feel I should get out there when I see the right opportunity and take a gig and work it.”

He’s played all over the planet; was there a kick to playing a quiet town like this one?

He chuckled: “I just go where there’s a gig.”

_Ajazzman steps out of the sideman's shade and sings, a per­sona for the public to consider. He makes an adequate living at it, but a better one helping other people make their own music. Still, those who hear him become members of a wildfire cult.

I’m one of them. It took some work. I didn’t take him serious­ly at first; I didn’t give him credit. I had to study a little—not just the music but the backstory, which, all things being equal, drives the music home. Charlie Parker’s aura was generated by his music, but his legend owes something to his suffering. Bob’s will owe something to his resilience and adaptability. His surviv­ability. Maybe that sounds melodramatic, but it fits the cult of Dorough. Even Mort Fega, always crisply professional, gushed when he was asked for his impression of Bob: “I can’t say enough nice things about him as a human being; and as nice as the things I might say about him as such, I’d say even nicer things about him as a musician—both a composer and a per­former. Does that sound like a love affair?”

Or sentimental? Let it go. Loosen up. Shed the hairshirt of high seriousness. Crack apart the frigid attitudes by which you’ve approached jazz music. Listen to Bob Dorough, and lis­ten again. After a while, the weird bliss gets through, and your prejudices begin to thaw. His selfless wit opens new paths to the jazz sublime, and you realize that, despite his obscurity, he is, in many respects, a genius.

I could go on. But I should probably just defer to that cur­mudgeonly hipster cousin of his whose line best describes what it’s like to succumb to the Dorough effect: I was so much older then; I’m younger than that now.