Incongruous Encounter: Frank Sinatra Meets Randy Newman

There have been some naturally skeptical reactions to the notion of Bob Dylan doing a cover album of songs associated with Frank Sinatra. With a voice that is more a rough in the diamond than the reverse, his about to be released Shadows in the Night stands to prove an interesting challenge that hopefully will yield better results than his crooning of Christmas carols a few years back. But Shadows in the Night got me thinking about another incongruous encounter between Sinatra and another unlikely performer long before he died.

I think it's safe to assume that when Frank Sinatra created Reprise Records in 1960, he didn't envision a line-up that would eventually include Tiny Tim, Jimi Hendrix, The Mothers of Invention, Captain Beefheart & His Magic Band, Neil Young, The Fugs and Randy Newman. However, by 1970, there they were, not to mention a host of others just like them – and here was Frank Sinatra situated among them. Curiously, at the time, Sinatra was also in need of a hit song. So he turned to an unlikely collaborator from his label: Randy Newman.

Frank Sinatra has been a best-selling artist for Capitol Records since 1953 after a long string of sensational albums. Sinatra possessed the kind of dreamy, forlorn voice that could reach down to the very essence of tenderness in a sad song. When he interpreted such indelibly sorrowful tunes as "I Can't Get Started," on No One Cares (1959), or "Willow Weep for Me," on Frank Sinatra Sings Only for the Lonely (1958), he would embody the song's anguish so effortlessly it was if the compositions were singing him. Sinatra had perfected a distinctly romantic style, a sexiness born of both heartbreak and despair. He played out the role of the lonely guy at the bar, nursing his glass of scotch, then imparting a lasting story of regret to you alone. In doing so, Sinatra could keep alive a slight flicker of romantic desire, hushed yearning or grievous moment that became more deeply intoxicating with every line he sang.

By the late Fifties, however, Sinatra's real unhappiness lay with Capitol Records. Disgruntled, he wanted out of his contract, citing exhaustion with the demands of the major labels. In Reprise, what Sinatra envisioned was an independent record label which might attract folks like fellow Rat-Packer Dean Martin and jazz music's true dignitary, Duke Ellington. But while Martin and Ellington eagerly jumped on the bandwagon, the Chairman of the Board still wasn't satisfied; he just wasn't making the huge impact he had years earlier. Sinatra's subsequent Reprise recordings didn't manufacture anywhere near the hits his years with Capitol produced. Even still, there was an abundance of wonderful songs. Who can forget the beautiful melancholic cadences of "Summer Wind," or the unquenchable craving of "Strangers in the Night," not to mention "That's Life," with its soulful swing? But by 1968, the songs were no longer singing him. Sinatra had grown far too comfortable in the role of the romantic icon. His cover of Paul Anka's self-pitying "My Way," for example, was so overwrought that it became a self-parody of the wounded romantic Sinatra had been playing for years. When "My Way" only climbed as high as #27 on the pop charts in 1970, Sinatra turned to Randy Newman. When Sinatra met Randy Newman in the studio, he found a singer-songwriter and pianist who was far from a wounded romantic, someone who shuffled shyly across the room as if trying not to be noticed. Yet Newman had already provided a nimble collection of songs for other proven performers including Dusty Springfield, who had just recorded "I Don't Want to Hear it Anymore" and "Just One Smile" for her soul classic Dusty in Memphis (1969), and earlier, in 1966, the unmatched heartbreaker "I've Been Wrong Before" (which would have been an ideal cover for Sinatra); the jaunty "While the City Sleeps" and the dark desperation of "Anyone Who Knows What Love Is (Will Understand)" for Irma Thomas; and the soft bossa-nova of "Take Me Away" for Jackie DeShannon in 1968. But the song he would dream up for Sinatra had the curious title of "Lonely at the Top."

What Sinatra clearly didn't know about Newman was that he was also a pop parodist. But most musical satirists who perform comedy songs ("Weird Al" Yankovic and Adam Sandler come to mind) commonly trash other, more famous, artists. After all, it's an easy way to create an instant hit record. Some, like "Weird Al," have built long careers solely on the backs on those they parody. When he demolishes Micheal Jackson's "Beat It," with his own "Eat It," it is nothing more than a one-note joke, one we feel perfectly safe in sharing because we aren't the butt of it. But Newman's work is cut from a different cloth. In his satirical numbers, parody is not an end in itself, it's merely a means to get at something more resonant in the target of the joke and to the culture that produced that target. Parodists like "Weird Al" and Adam Sandler also lay waste to the work of those with larger ambitions, but Newman is someone for whom artistic ambition is wrapped up in the question of what constitutes amusement and what constitutes art.

It's hard to say then if Newman wrote "Lonely at the Top" to take the piss out of the grandiose "My Way," or tweak the persona of the lone romantic, but a studio session was soon arranged for Newman to play Sinatra the song. Unlike "My Way," with its phony tough-guy platitudes, "Lonely at the Top" is a biting examination of the romantically fatalistic figure Frank Sinatra had spent a career creating. Sinatra pressed himself quietly against a studio wall while Newman crouched over the piano and slowly began to sing. As a piece of music, "Lonely at the Top" was your basic ragtime ballad, but the lyrics – spoken in the first person – were something quite peculiar. Not only did the song subtly mock the persona Sinatra had spent his career creating, it also caricatured the life and career of Newman himself: "I've been all around the world, had my pick of any girl," sang the unworldly Newman in his customary low drawl. "You think I'd be happy, but I'm not." Ol' Blue Eyes stood attentively trying to measure the meaning of this odd little ditty, while Newman continued his sly deconstruction of the Sinatra persona: "Everybody knows my name, but it's just a crazy game. Oh, it's lonely at the top." Could this clown be serious? Sinatra no doubt wondered. In all likelihood, Newman had already lost his big chance for a hit record, and by the song's conclusion, the jig was definitely up – "Listen all you fools out there/Go on and love me – I don't care/Oh, it's lonely at the top."

Without saying a word, Sinatra left the studio having made it perfectly clear there would be no hit song coming from Randy Newman. For his part, Newman wasn't terribly surprised, as he had immediately identified one of the significant differences between the two performers. Where Newman had written a character study of a man who couldn't find solace in being on top, Sinatra was an artist who believed that solace could only be found there. "It would have been real difficult," Newman recalled. "[Sinatra] couldn't have played many [types of] characters in his songs." Newman recognized that his song required that Sinatra distance himself from, even parody, the image he helped create. "He could have [truly got] it if he had this sense of humour and he actually was leaning against leaning against a lamppost, looking forlorn," Newman continued. But if you listen carefully to Newman sing "Lonely at the Top," you immediately catch the incongruities in the song, a caustic and clever ingredient that Sinatra surely resisted, and for good reason. Sung with a straight face, by any popular performer, Sinatra, or even Barbra Streisand (who also turned it down), the tune would lose its character and its point.

A couple of years after the fateful Sinatra session, Timothy Crouse, in Rolling Stone, elaborated on the discrepancy: "Although it was written for Frank Sinatra, 'Lonely' is really a parody of every self-congratulatory end-of-the-road song Sinatra ever sung." Since Newman was a "nobody," he could be anybody in his songs, a luxury Frank Sinatra, with all his fame, couldn't afford. "I can do personal stuff because no one gives a shit – no one knows who the hell I am," he said at the time. "But Sinatra can't sing 'Suzanne' [a Newman song about a rapist's fantasies] because he's somebody." After Sinatra's rejection, Newman sat down to write more songs and decided to keep "Lonely at the Top" for himself – as a cute joke in which the chap singing that he's lonely at the top hides a fear that he might actually be closer to the bottom. Newman eventually added it to live shows, the self-deprecating joke growing deeper each year he was continuously nominated for Academy Awards for his film music and rejected, and even included the track on his studio album, Sail Away, in 1972. Sinatra, meanwhile, abandoned recording and went into a brief retirement. But though the session did not produce a successful collaboration between these two radically different American performers, it proved to be an instructive experience for Newman. He could now put his futile attempt to emulate Sinatra behind him, and in the process, finally discover the paradoxical corners of his own voice.

**This piece is an edited and reconstructed portion from my book, Randy Newman's American Dreams (ECW Press, 2005).**

 - Kevin Courrier is a freelance writer/broadcaster, film critic and author (Dangerous Kitchen: The Subversive World of Zappa, Randy Newman's American Dreams, 33 1/3 Captain Beefheart's Trout Mask Replica, Artificial Paradise: The Dark Side of The Beatles Utopian Dream). Courrier teaches part-time film courses to seniors through the LIFE Institute at Ryerson University in Toronto and other venues. His forthcoming book is Reflections in the Hall of Mirrors: American Movies and the Politics of Idealism.