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Apr 25, 2025 By Arden Green

Frank Sinatra’s ninth studio album and overall artistic achievement In the Wee Small Hours remains among pop music’s most lusciously atmospheric recordings, its arrangements humming with a unique poetry all their own. An early prototype of the soon-to-be-popularized “concept” album, In the Wee Small Hours unites its 16 haunting tracks with a shared theme of melancholy, experienced, it would seem, while smoking ragged, filterless cigarettes beneath the ghostly indigo glow of ancient streetlamps, along an empty street late at night, while the rest of the world is fast asleep.

By 1955, the 40-year-old Sinatra was adrift at the center of midlife’s raging sea, his head full of liquor and a heart full of romantic anguish. Though still a tremendously popular act just entering his “golden age,” the adoring bobbysoxers of the pre-rock and roll 1940s who’d accounted for much of Sinatra’s early fan base had since matured, Elvis Presley was in between his debut and yet-to-be-realized international success, and eventual youth culture icon James Dean had made his big screen debut in Elia Kazan’s East of Eden a mere two weeks prior to In the Wee Small Hours’ release. Popularity, as many great artists have been forced to recognize, does not ensure relevance.

The times were shifting, with the enchanted age of early post-war optimism that Sinatra had known gradually slouching into a tumultuous era of adolescent alienation and societal restlessness, effectively paving the way for the following decade’s counterculture of political revolution and social upheaval. Surely, Sinatra recognized that the docile vocal jazz he’d once crooned in the name of young lovers had fallen out of favor, as he re-emerged onto the scene with an entirely new offering—which, though hardly confrontational as Elvis’ ascension would be, and by no means suited to a frustrated, disillusioned youth culture, as James Dean seemed, would serve as an act of personal creative reclamation on Sinatra’s part. Instead of retreading past hits or allowing himself to disintegrate into yet another nostalgia act, the ole Chairman teamed with producer Voyle Gilmore, arranger/producer Nelson Riddle, and audio engineer John Palladino to craft one of studio pop’s greatest exercises in technical ingenuity and artistic brilliance. Not only did Sinatra ensure his rightful place atop the era’s pop music throne, he upped his own ante, cementing himself as an artistic force to be reckoned with, even in the face of the emerging rock and roll movement.

As suggested by its noirish cover art, In the Wee Small Hours is a mistily dreamlit journey into the depths of depression and melancholia, its every corner awash in shades of blue. Sinatra’s amiable croon accompanies the listener through this sonic cycle of heartache, its rich orchestration and sleek production adding to its delirious effect as Sinatra reimagines the Great American Songbook (GAS) into his own midnight wonderland. Opening cut “In the Wee Small Hours of the Morning,” the album’s only non-GAS inclusion, beckons the listeners inside the dream with its gentle strings and tinkling piano notes. The track, which would quickly become a fan favorite and staple among Sinatra’s prolific discography, finds the iconic crooner exploring spaces far more vulnerable than before, singing Mann & Hillard’s lyrics as though they’d always been his own. Likewise, his emotive rendition of Duke Ellington’s “Mood Indigo” is especially affecting when experienced in the album’s melancholically atmospheric context. Other standouts include the haunting “Deep in a Dream” and intoxicating “Last Night When We Were Young,” the latter opening with the chillingly gorgeous tones of a ghostly harp, effectively drawing the listener deeper into the artist’s rheumy realm. So too, the heady sway of “I’ll Be Around” and rich moonglow fantasy “Dancing on the Ceiling” seduce listeners in a manner uniquely Sinatra. Even 70 years on, the album’s power is undeniable.
Throughout Sinatra’s illustrious six-decade career as an iconic singer and successful actor, Ole Blue Eyes produced his fair share of musical gems, great recordings that proved successful hits for him in his lifetime as well as timeless pop cultural treasures, but In the Wee Small Hours remains his aesthetic and artistic triumph. This critically acclaimed document of heartbreak and mournful dreaming tackles sentiments as perpetually relevant as they are universal. Comfort resides within the notes of this album, a seeping, saturating warmth to ward off the trials of a cold, lonely night. In the Wee Small Hours marked a crucial turning point for Sinatra as an artist, maintaining its often-overwhelming beauty even now. Enjoy to your lonely heart’s content and sink irretrievably into the night.

www.sinatra.com

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