Who did Sinatra say was the best singer? Unpacking Frank's Musical Pantheon

Frank Sinatra, the Chairman of the Board, the Voice – whatever you called him, Frank was undeniably one of the most iconic singers of the 20th century. His voice, his style, and his sheer charisma set a standard that few have ever reached. Given his towering status in the music world, it's natural to wonder: who did Frank Sinatra himself consider the best singer?

This is a question that has fascinated fans and music historians for decades. Sinatra was known for his opinions, often expressed with characteristic bluntness. While he rarely gave a single, definitive pronouncement on who was "the best," his admiration for certain artists shines through in interviews, his personal writings, and even his musical choices.

The Usual Suspects: Who Frank Admired

When delving into Sinatra's musical influences and his peers, several names consistently emerge as those he held in the highest regard. These weren't just singers he liked; these were artists whose craft, phrasing, and emotional delivery he dissected and respected.

The Masters of Phrasing and Emotion

Sinatra was a master of phrasing, the art of stretching or compressing notes to create a unique rhythmic and emotional effect. He learned from the best, and he wasn't shy about acknowledging his mentors. Among those he frequently cited or alluded to were:

Bing Crosby: Crosby was a pioneer of the popular song and a crooner whose relaxed, natural style deeply influenced a young Sinatra. Sinatra admired Crosby's effortless delivery and his ability to connect with an audience. He often mentioned Crosby as an early inspiration.
Billie Holiday: Her name is often brought up in discussions about Sinatra's deepest musical admirations. Holiday's raw emotion, her distinctive melodic interpretations, and her ability to convey profound sadness and joy with every note deeply resonated with Frank. He is quoted as saying, "Billie Holiday was the greatest influence on me." He admired her courage and her unique way of singing a song, making it her own. He felt she had a soul that poured out into her music.
Gene Kelly: While primarily known as a dancer and actor, Kelly was also a talented singer. Sinatra admired Kelly's rhythmic sense and his ability to imbue his singing with the same vitality and precision he brought to his dance routines.
Pee Wee Russell: A jazz clarinetist, Russell's influence might seem surprising, but Sinatra was a keen observer of all forms of musical expression. He appreciated Russell's unique, almost melancholic tone and his improvisational genius, which he saw as a parallel to his own vocal innovations.

The Great Ladies of Song

Sinatra had a particular reverence for many of the great female vocalists of his era, recognizing their equal, if not sometimes superior, command of the art form.

Ella Fitzgerald: "The First Lady of Song" was a titan of jazz. Sinatra lauded her incredible vocal range, her impeccable pitch, and her astonishing improvisational skills. He especially admired her scat singing, seeing it as a pure musical expression.
Sarah Vaughan: "Sassy" was another vocalist Sinatra held in immense esteem. He admired her unique vibrato, her sophisticated harmonic understanding, and her ability to take a song and imbue it with a richness and depth that was truly her own.
Lena Horne: Sinatra was a vocal supporter of Lena Horne and admired her elegance, her stage presence, and her powerful, yet controlled, vocal delivery. He saw her as a consummate professional and an artist who transcended genre.

Why This Nuance?

It's important to understand that "best" is subjective, especially in the arts. Sinatra, as a lifelong student and practitioner of his craft, understood this implicitly. He wasn't looking for a carbon copy of himself. Instead, he was drawn to artists who pushed boundaries, who possessed unique voices, and who could convey genuine emotion. His admiration was often for their approach to *interpreting* a song, their understanding of rhythm and melody, and their ability to tell a story with their voice.

Sinatra's own approach was deeply influenced by the jazz singers of his time, particularly their rhythmic sensibilities. He was a "singer's singer," and he respected those who treated the song as a living entity, rather than just a vehicle for vocal pyrotechnics.

"The singers I admired most were the ones who could really tell a story with a song... the ones who understood what the lyrics meant and could make you feel it."

- A paraphrase reflecting Sinatra's known sentiments.

The Verdict: A Pantheon, Not a Single King

Ultimately, if Frank Sinatra were to anoint a single "best singer," it would likely be a futile exercise. His "best" was a constellation of artists who, in their own unique ways, achieved a level of artistry that inspired and challenged him. He saw greatness in the raw emotion of Billie Holiday, the sophisticated swing of Ella Fitzgerald, the effortless cool of Bing Crosby, and the interpretive genius of Sarah Vaughan. These were not just contemporaries; they were fellow travelers on the journey of musical expression, each a master in their own right.

FAQ

How did Sinatra define "best singer"?

Sinatra generally defined "best" by a singer's ability to interpret a song, convey emotion, possess a unique vocal style, and demonstrate a strong rhythmic sense. He admired those who could make a song their own and tell a story with their voice, rather than just hitting notes.

Why did Sinatra admire Billie Holiday so much?

Sinatra frequently cited Billie Holiday as his greatest influence. He was deeply moved by her raw emotional honesty, her distinctive phrasing, and her ability to imbue her songs with profound feeling, even in their sadness. He saw her as a soul who poured her life into her music.

Did Sinatra consider himself the best singer?

While Sinatra was confident and proud of his own achievements, he was also a student of music and deeply respected the artistry of others. He rarely, if ever, declared himself the absolute best. Instead, he acknowledged his own place among the greats and consistently pointed to others whose artistry he admired immensely.

Were there other singers who influenced Sinatra besides those mentioned?

Sinatra's musical palate was broad. While the names listed are the most frequently cited, he also expressed admiration for various jazz instrumentalists and singers whose work contributed to his understanding of musicality, rhythm, and emotional delivery. His appreciation extended to the entire spectrum of great American popular song and jazz.