Frank Sinatra’s destiny was always to be a solo artist. Despite his immense popularity with the Tommy Dorsey Orchestra, Frank harbored an undeniable urge to forge his own path. In 1942, the musical landscape was different; singers typically found their place within the comforting structure of a big band. While solo performers like Al Jolson existed, they were not the norm. When Sinatra announced his departure to Dorsey, he was met with a reportedly harsh farewell. The narrative surrounding their parting is rich with detail and worth exploring further. Sinatra enlisted his trusted arranger, Axel Stordahl, and embarked on his recording career with Columbia.
The period between 1943 and 1952 represents a unique and often overlooked chapter in Sinatra’s illustrious career. For the author, these Columbia recordings serve as an origin point for their own musical discovery. In the early 1990s, navigating the nascent appreciation for jazz and traditional pop, the author was unsure of where to direct their musical exploration, seeking a sound beyond the popular rock and roll figures of the era. A significant part of this early exploration involved a cassette tape that formed half of a box set dedicated to Sinatra’s Columbia recordings, leading to a familiarity with these lesser-known tracks before encountering his more famous Capitol records.
This era frequently gets overshadowed because Sinatra’s solo career experienced a general decline shortly after its inception. Both the musical material and Sinatra’s performance capabilities seemed to falter. It’s difficult to fathom now, but for various reasons, by the early 1950s, Frank Sinatra appeared to be a fleeting sensation – a singer who shone brightly with a popular big band but struggled to maintain solo momentum. Furthermore, during a time when societal morals were strictly upheld, Sinatra’s personal life was in considerable disarray. His separation from his wife, Nancy, and his tumultuous relationship with the glamorous and popular actress Ava Gardner, undoubtedly impacted his public image. Such a lifestyle could be detrimental to a career, as the public expected a certain level of decorum from its stars. Sinatra’s stormy romance with Ava visibly affected his artistic output and judgment. This was also the era of the “novelty” song, characterized by quirky lyrics and nonsensical themes. Although Sinatra did venture into the bizarre with the infamous “Mama Will Bark,” he largely resisted the urge to simplify his artistic ambitions for wider appeal, finding little space or acceptance for high-quality vocal performances. Moreover, the quality of his voice had begun to diminish. Amidst this turmoil, Frank persevered, but after a period of strong performance in the mid-1940s, both his popularity and his artistic skill began to wane.
However, delving into the recordings from this period reveals another facet of Sinatra’s career that offers immense enjoyment and evokes warm feelings. Much like his big band recordings, the Columbia sides are perfectly suited for relaxed listening at home. This era is often neglected due to Sinatra’s overall decline, but while the recordings may not withstand rigorous critical examination, they are undeniably enjoyable for fans. This is the essence of this period: brilliant from a fan’s perspective, yet somewhat lacking from a critical standpoint. For those interested, The Complete Recordings: The Columbia Years 1943-1952 is highly recommended, available on iTunes and eBay. A more accessible option is The Best of the Columbia Years, a 4-CD set. The following are the top ten Frank Sinatra recordings from his time after leaving Dorsey in 1943 until his signing with Capitol Records ten years later.
Top Ten Columbia Era Recordings
“Dream” (1945) — As mentioned previously, many of Frank’s early recordings possess a profound nostalgic charm. For enthusiasts of the 1940s and 1950s, this music transports listeners directly to that era. “Dream” exemplifies this perfectly, with a shimmering quality that seems to descend from above. Penned by the legendary Johnny Mercer, it became a #5 hit for Frank and was revisited on his 1960 album Nice ‘n’ Easy.
“April in Paris” (1950) — The sentiments expressed for “Dream” apply equally here. This standard is rendered beautifully by a young Frank, with an “absolutely gorgeous” rendition. He would re-record it seven years later for his Capitol album Come Fly With Me. This song is also a signature piece for the Count Basie Orchestra.
“Castle Rock” (1951 – with Harry James) — This track is a genuine powerhouse. Columbia’s idea to reunite Sinatra with his former bandleader, Harry James, resulted in three songs, two of which feature on this list. “Castle Rock” is an electrifying piece arranged by Ray Conniff. Both Sinatra and James deliver ferocious performances, sounding exceptional. A personal anecdote recounts the author’s initial misinterpretation of Sinatra’s exhortation to the trumpeter, thinking he was addressing Harry Connick, Jr. This collaboration, however, was with Harry James. Historically, James himself was not particularly fond of this track, deeming it “the worse thing that either one of us ever recorded.” This author respectfully disagrees.
“Sweet Lorraine” (1946) — While not strictly a “jazz singer,” Frank Sinatra undeniably showcased his jazz sensibilities on numbers like this. Sinatra’s vocal performance “swings like a mother,” demonstrating his early mastery of using his voice as an instrument, with impeccable phrasing and timing. The backing by the Metronome All-Stars jazz ensemble is equally superb, featuring excellent solos and piano work by the future superstar Nat “King” Cole. “Sweet Lorraine” would also become a signature tune for Cole.
“Deep Night” (1951 – with Harry James) — Another collaboration between the reunited Sinatra and James, this track lives up to its title, offering perfect late-night listening. Sinatra’s vocal possesses a wonderful cadence and flow, while James imbues the piece with all the noir-like nuances imaginable within its three minutes. The arrangement includes a powerful brass interlude before Sinatra’s smooth return with the line, “Coooome to my arms, my darling…”.
“Saturday Night (is the Loneliest Night of the Week)” (1944) — For those creating a non-chronological playlist from this Sinatra era, this song is an ideal starting point. Its high-energy opening, lively horn arrangement, and Frank’s swinging performance make it a standout uptempo number from this period. It’s pure fun.
“Autumn in New York” (1949) — Similar to “April in Paris,” this is a beautiful song that Frank imbues with his signature quality. He would later revisit it on Come Fly With Me. The exquisite string arrangement evokes the atmosphere of a post-war Manhattan sidewalk adorned with falling golden leaves. While a standard, Sinatra’s version is the only one to have charted in the U.S., reaching #27 in 1949.
“You Can Take My Word for It, Baby” (1946) — This ranking may surprise some devoted Sinatra fans. On this lesser-known track, Frank is accompanied by the Page Cavanaugh Trio, whose style bore a strong resemblance to the Nat “King” Cole Trio. Critics at the time often dismissed such recordings as trivial attempts by Sinatra to recapture his former pop music prominence. However, this tune radiates charm and exemplifies the delightful quality of the era’s pleasant, intimate ditties, presenting a wonderful light jazz performance.
“I’m a Fool to Want You” (1951) — The omission of this song from the #1 spot might draw criticism from music aficionados. If one were to select a handful of songs representing Sinatra’s artistic development at various stages, this recording would stand out as the pinnacle of his pre-Capitol era. Crucial context involves Sinatra’s tumultuous relationship with Ava Gardner during this period. Their intense personalities often led to frequent arguments. Sinatra, a deeply emotional individual, was profoundly affected by the difficulties in his relationship with Ava. The legend holds that Sinatra himself contributed to the lyrics to better reflect his personal situation. Another popular tale suggests that, in a state of deep despair, Frank entered the studio late at night, delivered a raw, emotional vocal in a single take, and departed into the night. Regardless of the accuracy of the one-take story, the recording undeniably stands as one of the most heartfelt performances of his career. While he revisited the song for his 1957 album Where Are You?, his original rendition captures an open vulnerability. It is noteworthy that the novelty song “Mama Will Bark,” a collaboration with actress Dagmar and actual dogs, released as a single in 1951, bizarrely featured “I’m a Fool to Want You” as its B-side.
“Poinciana” (1946) — This choice might also raise eyebrows among Sinatra enthusiasts, but its charm is undeniable. Sinatra’s sole recording of this Cuban melody subtly drifts into the listener’s consciousness, seemingly from an ethereal source. It evokes the feeling of stepping back in time, perhaps through an old radio in a grandmother’s attic on a classic episode of The Twilight Zone. The song possesses a unique quality of being perfectly “stuck in its time.” Frank’s wistful rendition of “poiiiinciana…,” accompanied by a lilting flute and sweeping strings, creates a dreamy, transportive experience.
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