Pop culture can be as forbidding as it is inviting, particularly in areas that invite geeky obsession: The more devotion a genre, series, or subculture inspires, the easier it is for the uninitiated to feel like they’re on the outside looking in. But geeks aren’t born; they’re made. And sometimes it only takes the right starting point to bring newbies into various intimidatingly vast obsessions. Gateways To Geekery is our regular attempt to help those who want to be enthralled, but aren’t sure where to start. Want advice? Suggest future Gateways To Geekery topics by emailing email@example.com.
Geek obsession: Frank Sinatra
Why it’s daunting: The story of the 20th century is the story of Frank Sinatra. Born in 1915, the massively popular entertainer died in 1998—and during those 82 years, he intersected almost every major pop-culture trend as a leader, a dabbler, or an icon to react against. His towering legend alone is enough to make him an intimidating singer to approach, although that’s offset by the aura of quaintness that his music has been saddled with by later generations. Sinatra’s music transcends all that. His oeuvre may be staggering in its volume and scope, but at its heart is one simple, sturdy quality: his voice, which was supple, soulful, dimensional, tender, and titanic enough for Sinatra himself to be forever nicknamed The Voice. With a catalog as vast and pervasive as his timbre and his ambition, Sinatra casts a long shadow; it can be difficult to pick through his dozens of albums and hundreds of singles to find a concise, easily absorbable portrait of the artist-in-song.
Possible gateway: Songs For Swingin’ Lovers!
Why: Many anthologies of Sinatra’s classics exist, but the vast majority rely too much on threadbare hits; by doing so, they fall short in providing a snapshot of Sinatra in his zeitgeist-defining prime. Songs For Swingin’ Lovers! is that snapshot. Released in 1956, the album helped solidify the 41-year-old Sinatra’s triumphant comeback after his career fell into a slow tailspin in the post-World War II years. Gone was the wide-eyed gawkiness of his Columbia Records period, an era where he set the template for every teen-idol trend to follow, from The Beatles to Justin Bieber. In its place was a measured, effortless grace. Mature yet universal in its appeal, Songs For Swingin’ Lovers! collects a seamless string of jazz and pop standards, from the breezily ebullient “You Make Me Feel So Young” to the Cole Porter cork-popper “Anything Goes,” impeccably arranged by Nelson Riddle and delivered by Sinatra with a cool, career-defining joie de vivre. The “Swingin’” in Songs For Swingin’ Lovers! doesn’t just refer to the swing of the songs themselves; this is a wiser, stronger Sinatra, rocketing out of his corner with a spring in his step and both dukes up.
Next steps: For every outburst of joy and triumph that Sinatra mustered during his storied career, he also dwelled in the quieter, moodier side of the human psyche. Brooding and steeped in atmosphere, 1955’s In The Wee Small Hours is the lonely, after-hours companion to Swingin’ Lovers. This one also features Riddle at the arrangement helm, and Sinatra lets his voice float like a muted foghorn over the Bob Hilliard/David Mann-penned title track, a lament to absence and loss, which Sinatra introduced to the world and forever made his own.
Loneliness is even more palpable on, aptly enough, Frank Sinatra Sings For Only The Lonely. The 1958 album isn’t a collection of torch songs as much as a study in shadows; with heart-stopping intimacy, Sinatra renders chestnuts like “Angel Eyes” into entirely vital things. Sinatra’s greatest strength always rested in his unique convocation of conversational, behind-the-beat cadence and deceptively crisp phrasing. Here, his mix of confession and technique melt into an overwhelming, elemental whole. Sinatra is generally credited with popularizing the concept album, long before The Who did so in the rock world, and nowhere is that more poignantly evident than on Only The Lonely.
As if to counterbalance the cathartic heft of Wee Small Hours and Only The Lonely, Sinatra buoyed 1959 with Come Dance With Me! His rendition of Johnny Mercer’s “Something’s Gotta Give” is telling; balancing his darker tendencies against his bubbly side, Sinatra exhibits a rounded, complex vision of ’50s America—just as the seismic upheaval of rock ’n’ roll was about to alter the cultural landscape forever. His status as crooner du jour was being vigorously disputed by the likes of Ray Charles and Sam Cooke, but Sinatra rose to the challenge with a bouncy sock-hop soundtrack that marked one last jitterbug of innocence before the tumult of the ’60s.
Sinatra switched from Capitol Records to his own imprint, Reprise, in 1961. It led to a string of records that decade, most of which were hits despite flying in the face of the decade’s emerging youth culture. Sinatra resisted that trend at first, although he succumbed to the tide of history by eventually covering everyone from The Beatles to Simon & Garfunkel. On September Of My Years, though, the 50-year-old singer made one of the bravest statements of his career: Just as trusting people over 30 became taboo, he acknowledged, embraced, and romanticized his middle age. With lush yet suitably subtle arrangements by longtime collaborator Gordon Jenkins, Sinatra turned songs like “It Was A Very Good Year” into anthems for the inexorable march of time.
Sinatra anthologies are, for the most part, spotty and myopic, hewing too closely to theme, era, or label. Sinatra: Best Of The Best corrects that. The 2011 collection is, startlingly, the first affordable way to get the best of both his Capitol and Reprise output in a single package. From the well-worn yet still thrilling highs of “My Way” and “Theme From New York, New York” to the timeless understatement of “Summer Wind” and “Fly Me To The Moon,” Best Of The Best lives up to its title. And while the optional second disc contains a stellar live set from 1957, the one-disc anthology of studio smashes is the way to go—and the best single conglomeration of Sinatra’s bestsellers currently available.
Where not to start: Although the deluxe, 20th-anniversary reissue of 1993’s Duets came out this month, it is not an ideal introduction to Sinatra’s music—nor are any of his post-’60s albums. Neither is Sinatra’s earliest studio output in the ’40s a great first impression, as spunky and fun as they are. In the ’60s, he also leaned on a series of collaborative albums—with the likes Count Basie, Duke Ellington, and Antonio Carlos Jobim—that succeeded in shining a fresh light on Sinatra’s talents, even as they resulted in lesser entries of his discography as a whole. Sinatra always shared the spotlight grudgingly and sparingly, which was his prerogative as a singer whose heart-stopping tone could permeate every nook and cranny of any recording or concert hall. But it also yielded embarrassing mismatches like Duets’ team-up between Sinatra and Bono on “I’ve Got You Under My Skin.”
In addition to music, film was a platform for Sinatra’s free-flowing charisma. Most famously, his gripping (if scenery-chewing) turn in 1953’s From Here To Eternity earned him an Academy Award. He’s just as scene-swallowing in 1955’s The Man With The Golden Arm, but his most enduring tenure in cinema is with more lighthearted fare—specifically his movies with The Rat Pack, the boys’ club of suave entertainers he belonged to in the ’60s. Yet as magnetic as Sinatra could be on celluloid, music is the first, last, and best medium through which to discover this essential 20th-century icon.