Where to start with the music of Ol’ Blue Eyes himself, Frank Sinatra

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 protected].
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.