Fifty-one years ago, Frank Sinatra broke away from Capitol Records to form his own company, Reprise, launching the label with the 1961 album Ring-A-Ding-Ding! With Capitol, Sinatra had matured from a temperamental pop idol to a real artist, working to champion great American songwriters and musicians while popularizing the idea of “concept albums” built around a single theme or mood. But Sinatra could still be prickly, so at the peak of his power (and with his contract up), he set out to prove that Capitol needed him more than he needed it. With Reprise, Sinatra pledged to give himself and his colleagues the license to push themselves. As it happened, Sinatra’s commitment to artistic freedom coincided with a decade in which popular music would go through rapid and radical changes. As it also happened, Sinatra had long been a vocal opponent of many of those changes, dating back to the emergence of rock ’n’ roll as a viable genre in the ’50s. So Sinatra’s career in the ’60s—and the fate of Reprise Records—would become a case study in how a savvy entertainer and businessmen can both coast and crash on waves he doesn’t fully comprehend.
Concord Records reissued Ring-A-Ding-Ding! last month, and it’s still as bright and brassy a record now as it was 50 years ago. Unable to work with Nelson Riddle or Billy May—because they were still under contract to Capitol—Sinatra tapped 35-year-old horn-player Johnny Mandel, who’d garnered acclaim for composing the jazzy soundtrack to the grim 1958 melodrama I Want To Live! Mandel’s orchestrations for Ring-A-Ding-Ding! are less lush and more playful than Sinatra’s ’50s records. The song “Let’s Fall In Love,” for example, begins with big horns, which give way to romantic strings and peppy flute, all in the space of about 30 seconds. Then, a minute in, Sinatra hesitates for a full two seconds over complete silence before jumping into the chorus. One of Sinatra’s great gifts as a vocalist was his conversational quality, and here Mandel’s music matches that off-the-cuff/hey-I-just-thought-of-something vibe.
Sinatra’s spirits are bright on Ring-A-Ding-Ding!—almost aggressively so. He wanted to make a strong impression with his first Reprise record, so he banished the ballads and served up the swing, almost exclusively. The songs on the album are short, eschewing the complicated intros Sinatra sometimes indulged in, and instead investing standards like Gershwin’s “A Foggy Day” and Cole Porter’s “In The Still Of The Night” with the zip and optimism that people often associate with the early days of the Kennedy administration. Sinatra even revived a novelty number from his ’40s act, “The Coffee Song,” about how there’s so much coffee in Brazil that the natives don’t drink anything else. (“The politician’s daughter was accused of drinking water and was fined a great big $50 bill.”) The song is an early example of Sinatra’s efforts to spread the gospel of Latin music to his fans, but also an indicator of how loose and ready to entertain he was feeling as this new adventure began.
Capitol, meanwhile, responded to Reprise by digging into its vaults, releasing Sinatra’s Swingin’ Session!!! two months before Ring-A-Ding-Ding! and Come Swing With Me! three months after, hoping to saturate the market and drown out Sinatra. The strategy failed—at least where this first record was concerned. Like nearly everything else Sinatra was involved with circa 1961, Ring-A-Ding-Ding! was an unqualified success. Reprise, on the other hand, had a rougher launch, with the non-Sinatra records selling less than the proprietor had hoped. In 1963, Sinatra accepted a buy-out offer from Warner Bros., which had long wanted the singer in its stable. Under the direction of Warner—and specifically Reprise president Mo Ostin, whom Sinatra had originally hired away from Verve—Reprise developed a reputation as one of the most adventurous and quality-driven labels of the ’60s and ’70s. At various times over those two decades, the Reprise roster included The Kinks, Lee Hazlewood, Fleetwood Mac, Joni Mitchell, Captain Beefheart, Frank Zappa, Jethro Tull, T. Rex, Neil Young, Tiny Tim, The Fugs, Arlo Guthrie, Pentangle, The Meters, John Cale, Richard Pryor, The Beach Boys, and Nancy Sinatra.
The success of the lattermost was greeted by Frank Sinatra with a mix of pride and rue. On his popular ’60s TV specials, Sinatra sometimes introduced himself as “Nancy’s father,” and made jokes about her rapid rise up the charts in a tone that subtly implied that her success was an indictment of a pop music business that had lost its damn mind. While ever-younger and shaggier record company executives seemingly threw money at any longhair who could scream on-key 70 percent of the time, Sinatra—ever the dedicated muso—spent the ’60s recording albums with Count Basie, Duke Ellington, and Antonio Carlos Jobim. He paid tribute to his own career on the best-selling A Man And His Music, and contemplated his obsolescence on September Of My Years. The latter two albums were released within a month of each other in 1965, and did so well that Sinatra regained his chairman-of-the-board swagger on the 1966 albums Strangers In The Night and That’s Life. But by the end of the decade, Sinatra found himself trying to maintain those hot sales by pandering (at last) to the young set, recording songs by the likes of Hazlewood, Mitchell, Paul Simon, and The Beatles. Sinatra ended the ’60s with the odd A Man Alone, a collection of tuneless songs written by drippy poet Rod McKuen, then began the ’70s with the poor-selling but brilliant Watertown, a sort of “pop opera” about a struggling single dad, with songs co-written and produced by The Four Seasons’ Bob Gaudio. While still popular as a concert attraction and with the “golden oldies” crowd, Sinatra’s broader commercial momentum had stalled.
I confess to a certain fascination with how pop music’s biggest stars weather these kinds of changes in their profession. I could write another whole article (and plan to someday) about how some of the most staunchly anti-rock New York folkies added more electric guitars and drums to their records as the decade progressed, often to wonderful effect. Similarly, by the end of the ’60s even some of the tamest pop stars were hiring edgy songwriters and producers to help them craft their very own semi-psychedelic song cycles. The same sort of decision-points would arise for platinum-level rockers in the ensuing decades: first when disco emerged, and then again in the mid-’80s when the prevailing production style leaned heavy on synthesized sounds, and yet again in the ’90s, when critics trumpeted the death of rock and declared that electronica was the future. Working musicians with long, thriving careers have to give some thought periodically to what their job description entails. Are they obliged to keep up with the times? Never mind what it takes to maintain a position in the marketplace; if they courted a young audience at the start of their career, do they want to keep thinking of themselves as young and hip?
It’s awfully hard for musicians to hold onto the younger demographic over the decades. More often, the fan base ages along with the artist, and eventually shrinks. And those fans that do stick around sometimes resist a star’s attempts to contemporize. The same critics who were electrified by Bob Dylan’s embrace of rock ’n’ roll in the mid-’60s, for example, were less forgiving when his records got slicker in late ’70s, even though Dylan was just keeping up with the times as he’d done the decade before. (See also: Empire Burlesque, Dylan’s most ’80s-sounding album.) And almost no one bought Sinatra’s Watertown, even though its downbeat theme wasn’t too far removed from his classic ’50s albums In The Wee Small Hours and Only The Lonely. It didn’t matter; the modern pop production eluded the older audience, while Sinatra himself remained too fusty for the kids.
Of course, that failure was still nine years away when Sinatra released Ring-A-Ding-Ding!, on the label he founded himself, while he was still one of the biggest stars in the world. Sinatra could’ve done just about anything he wanted as a recording artist in 1961, and would’ve gotten a fair hearing. His choice? To deliver a surefire hit, tweaking his popular “swing” sound with Mandel’s snazzy arrangements and an upbeat tone. Yes, there would be challenges ahead, for Sinatra and the country. There would be choices, and divisions, and Sinatra wouldn’t always end up on the right side of the lines that were about to be drawn. But perhaps because of those changing times, he’d make some of his most fascinatingly eclectic albums in the decade to come, bouncing between modernization and an almost petulant recidivism, sometimes within a matter of months. Only in the first chapter of the “Sinatra in the ’60s” story was everything spectacularly sunny. Back then, the singer considered what he’d been through, guessed at what lay ahead, and crooned, “Let’s Face The Music And Dance.”