Sinatra Sings the Great Songwriters

Lore & Background

By 1966, Sinatra had spent over two decades on the road, on television, and in the studio, and the Great American Songbook was no longer a repertoire to be conquered—it was a language he spoke fluently. The concept behind this album was deliberately editorial: rather than a grab-bag of standards, each side (or section) was anchored to a particular songwriter's legacy, inviting the listener to hear how Sinatra's timing, breath, and subtle vocal coloration interacted with, say, the wry wit of Cole Porter versus the sweeping romanticism of Rodgers and Hammerstein. It was a statement of respect as much as a performance. The collaboration with arranger-producer Billy May was a natural one. May's mid-1960s arrangements for Sinatra tended to be warm, slightly behind-the-beat, and generous with space—giving the voice room to lean, to push a syllable, to let a note hang a half-beat longer than the score strictly demanded. That sense of conversational ease, of a man sitting across from you at a dimly lit bar, is the album's signature texture. It is not the bombastic orchestral spectacle of the Capitol era; it is something more intimate, more considered. Fans often point to this record as evidence that Sinatra's artistry deepened rather than plateaued in his fifties. The phrasing is less showy, more surgical. Where a young Sinatra might have leaned on volume or a dramatic key change, the 1966 Sinatra earns his emphasis through restraint, through the micro-decisions of where to breathe and where to let a lyric land in silence. It is the work of an artist who has stopped performing and started telling.

In Their Own Story

The studio was quiet past two in the morning. Billy May had already walked out, satisfied, leaving the console warm and the tape rolling in standby. Sinatra stood at the mic with his hands loosely in his pockets, a half-empty glass of something amber on the stool behind him. He had just taken a song—something with a melody that climbed and a lyric that whispered—and he ran it back one more time, not because it was wrong, but because the second take let him find the exact spot where the singer's voice should crack, just barely, just enough. He nodded to the engineer, lifted the glass, and said, "That's the one." The tape kept spinning. The city outside the studio windows was already waking up, but in that room, the song was still breathing, still alive, still his.

Reader's Guide

1966 · Reprise Records · Produced by Billy May. Sinatra Sings the Great Songwriters arrived in the middle of Sinatra's most artistically self-directed period, the era when he owned his own label and could shape a record's arc without a major-label A&R committee breathing down his neck. The album's organizing principle—grouping songs by their original composer and lyricist—gave it a quasi-educational, almost anthology-like quality that set it apart from the typical Sinatra LP of the era. The mood is warm, unhurried, and deeply conversational; Billy May's arrangements sit slightly behind the beat, leaving generous pockets of silence where Sinatra's phrasing can stretch, dip, and surprise. Standout moments include Sinatra's treatment of Rodgers and Hammerstein material, where his baritone carries the romantic weight of the score without tipping into sentimentality, and his readings of Irving Berlin and Cole Porter numbers, where his dry, almost sardonic timing turns a wry lyric into a small act of theatrical comedy. The Bacharach-and-David numbers on the record showcase a different Sinatra—more rhythmic, more playful, more in step with the contemporary pop landscape without sacrificing his signature vocal color. The album charted solidly on the Billboard pop LP list and was well received by critics who praised its cohesion and Sinatra's interpretive depth. While it did not generate a single breakout radio single in the way some of his earlier records did, it became a staple of the "serious Sinatra" listening canon and remains a go-to recommendation for newcomers who want to understand why his voice was considered a major interpretive instrument. Fan takeaway: If you want to hear Sinatra not as a legend being performed but as a man in a room, thinking about a line of poetry and deciding, in real time, exactly where the comma should fall—this is the record.

Did You Know?

• The album's concept of grouping songs by individual songwriter was somewhat unusual for a pop LP in the mid-1960s and gave the record an almost programmatic, concert-suite structure that listeners still discuss today.
• Billy May, the producer and arranger, had been working closely with Sinatra through the early and mid-1960s, and his slightly behind-the-beat, spacious arrangement style is a defining sonic fingerprint of this era of Rep
• Sinatra's ownership of Reprise Records meant he had final say over track selection, sequencing, and the album's overall editorial concept—a level of creative control that was rare for a pop artist of his stature at the t
• The album is often cited by vocal coaches and music journalists as a masterclass in phrasing: how a singer can take a well-known melody and make it feel newly written simply by shifting where the breath falls and how lon