Sinatra Sings George & Ira Gershwin

Lore & Background

By the mid-1960s, Sinatra had long since left the Capitol Records era behind and was operating under his own banner, Reprise, with a creative freedom that earlier contract years never afforded. Choosing to dedicate an entire LP to the Gershwin brothers was a statement of artistic respect as much as commercial ambition. The Gershwin catalog had been a fixture of Sinatra's live sets for decades, but a studio commitment to the material—tracking it in a single, uninterrupted emotional arc—was a rarer and more deliberate act. The result is an album that sounds less like a collection of songs and more like a single, winding conversation with the past. The production, under Jack Pleau's steady hand, favors a lean, jazz-ensemble palette: acoustic piano, upright bass, a small horn section, and brushed drums. There is no orchestral bloat here; the space around Sinatra's voice is wide and dry, letting every syllable and every half-step of his phrasing land with crystalline clarity. This restraint became a signature of his Reprise period and is perhaps nowhere more apparent than in the way he lets silence do the work between phrases on ballads like 'Embraceable You' or 'Love Is Here to Stay.'

Critics and fellow musicians have long noted that Sinatra's Gershwin recordings from this era reveal a singer who had stopped performing and started *telling*. The swagger is still there in the uptempo numbers, but it is the quiet, almost whispered delivery on the slower pieces that separates this album from his earlier, more theatrical Gershwin work. It is Sinatra as a storyteller who has finally stopped winking at the audience and is simply telling the truth.

In Their Own Story

The studio lights are dimmed to a warm amber. Sinatra sits at a small round table, a glass of water within reach, his eyes half-closed as the pianist lays down the opening chords of 'The Man I Love.' He does not open his eyes. He hums a single note, adjusts his position on the stool, and when he finally speaks the first line, it sounds less like a performance and more like a memory he is letting slip out of his pocket. The engineer, watching the VU meters, notices that the needle barely moves on the quiet passages—Sinatra has dropped his volume to a near-whisper, trusting the room, trusting the listener, trusting that the words alone are enough. Somewhere in the control room, Jack Pleau nods once and makes a small mark on his notepad. The take is good. They will not do another.

Reader's Guide

1966 · Reprise Records · Produced by Jack Pleau

This album stands apart in Sinatra's discography for its singular focus: an entire LP devoted to the Gershwin brothers, arranged in a flowing arc that moves from playful swing to aching balladry without a single filler track. The mood is intimate, almost parlor-like, with a lean jazz ensemble that leaves generous space for Sinatra's phrasing to breathe. It captures him in the reflective, post-Capital era when his voice had deepened into a smoky baritone and his approach to a lyric became more narrative, less theatrical. Standout tracks include 'I Concentrate on You,' 'Embraceable You,' 'The Man I Love,' 'I Got Rhythm,' 'But Not for Me,' 'Fascinating Rhythm,' 'I've Got a Crush on You,' and the devastating 'Love Is Here to Stay.' The album earned a Grammy Award, cementing its place as one of Sinatra's most critically revered studio recordings. Fan takeaway: If you only own one Sinatra album and you want to hear the man *think* his way through a song rather than simply sing it, this is the one to press play on.

Did You Know?

• The album was recorded during Sinatra's Reprise Records era, a period when he had full artistic control over his releases and was no longer bound by a major-label A&R schedule.
• Sinatra had been performing Gershwin songs in his live shows and on earlier recordings since the 1940s, but this was one of the first times he committed an entire studio session to the Gershwin catalog as a unified artis
• The lean, small-ensemble production style on this record became a hallmark of Sinatra's mid-to-late 1960s Reprise albums, contrasting sharply with the big-orchestra sound of his earlier Capitol recordings.
• The album's track selection spans the Gershwin brothers' output across roughly three decades of Broadway and film, giving listeners a compressed survey of their songwriting evolution in a single sitting.