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I'm not sure of your experience in jazz singing, but all the songs you mention are standards in the jazz vocal repertoire - Skylark is performed and recorded every bit as much, if not more, than The Man I Love.
The songs of the first half of the 20th century created the template for jazz, and not just jazz singing. Most of the compositions in jazz follow the simple 12-bar blues and the 32-bar pop song form. The pop music of the rock and R&B era followed a verse-chorus form that, with repeated refrains and adolescent harmonies, offered little for the jazz improviser to work with; therefore, the songs from the "Golden Age" of American songwriting - 1920-1960 - continue to be interpreted in jazz.

As for what distinguishes singers, well, you are right and wrong at the same time: it is deeper than what we hear, but their sound is how we are able to perceive what goes on in the mind and soul of an artist.
How we create music is a balance of knowledge: knowledge of one's instrument, knowledge of the music- the particular idiom and its songs, and, of course, knowledge of oneself.
This last point cannot be overemphasized. Although many singers do not consciously analyze themselves and their lives, at some level they must come to terms with who they are, basically, as persons. All that they have experienced should be present in the creative process: what songs they are attracted to, and how they choose to present them.

Two of the most exceptional singers in jazz were Billie Holiday and Sarah Vaughan. They make for an interesting case study for how an artist develops.
>Billie was born to teenage parents who didn't last long together. Raped as a child, she was sent to live with a relative in a brothel. After growing up in 'the life', she decided to try for a job as a dancer; when it was clear she couldn't dance, she tried singing (never, did she ever believe she could really sing). Her small, intimate sound was refreshingly different from the blues shouters that were popular at the time. She also was inspired by the relaxed phrasing of Louis Armstrong, and enjoyed playing with the melody, but subtly, never upstaging the lyric, for Billie was a storyteller. The story she told was always her own: in her early recordings, you hear a hopeful young woman, longing for the love and care she never had; later, when drugs, abusive men and the racial climate of the time took its toll, the story changed. Then we heard a woman who had lost hope of happiness, yearning out of mere habit. The songs she sang in each era of her career were basically the same, but the change in delivery reflected her life.
>By contrast, Sarah lived in a fairly stable home, taking piano lessons from the church organist, thus explaining her exceptional musicianship. Following in the footsteps of Ella Fitzgerald, she entered the amateur contest at the fabled Apollo Theater in Harlem, and won.
Joining Earl Hines' band with singer/mentor Billy Eckstine, Sass was loved by all the musicians in the band, and was one of the gang. She drank, smoked, cursed, got high and got laid with them. Supremely confident in her abilities, she never backed down from anyone on issues of music or anything else.
Her studied voice had an operatic quality at times, which she gloried in (Marian Anderson was one of her heroes). Many times she would sing a phrase in such a way that pleased her sonically, regardless of the lyric. Where Billie spent her time onstage telling the story of her life, Sarah saw herself as an instrument, and her concerts were exhibitions of what that amazing voice could do.
Sass also was married often, but never was a victim. Her years of substances never affected her singing - she was much too respectful of her instrument to allow that - but she did finally succumb to lung cancer.
When she died, however, she had money in the bank, real estate, stocks, a full schedule of concerts and appearances, and a legacy of excellent recordings.
Billie, on the other hand, died handcuffed to a hospital bed, under arrest for narcotics. She had $500 taped to her leg, given by a reporter as an advance on an 'exclusive' for her story.

I believe that music is a spiritual gift, coming from a place outside of us, beyond us. The time we spend in practice and study is so that, when music comes, it can pass through us to the listener with the least amount of conscious thought on our part. when we are in that zone, we become more open, more vulnerable, more honest in our emotional expression than would ever be possible in our usual, deliberated state (yes, de-liberated).
So you are right: the making of music is deeper than what songs or notes to choose. It is a freeing of the mind and spirit to allow something magical to occur - in the artist and the listener. However, just as someone can get a lucky break in the stock market or sink a difficult shot on a basketball court, these moments are rare and fleeting without the discipline of study and training, respect and care for one's instrument, and the understanding that music deserves, demands such a committment.
The beauty that repays that committment is beyond measure...