Frank Sinatra transformed popular music. Often cited as the single finest interpreter of American standards, he influenced generations of vocalists such as Nat King Cole and Carmen McRae by focusing on phrasing and matching narrative nuance and emotional naturalism with amazing breathing control. In the 1930s, Sinatra starting bringing back “old” songs by such masters as Cole Porter while he was still a Big Band singer. He became a national institution in the ’40s, and even though Ray Charles has praised the flawless technique of this Columbia period, Sinatra kept evolving. Starting in the ’50s he concentrated on groundbreaking concept albums and a fresh Big Band sound with master arranger Nelson Riddle. Sinatra explored every nuance of emotion on these Capitol and Reprise albums and influenced the work of Ella Fitzgerald and Peggy Lee. Beginning in the ’70s, when rock ruled, his voice and output became erratic but some brilliant work remains. Though Sinatra always viewed himself as a popular singer, jazz musicians hold his work in the highest esteem. Miles Davis and Lester Young often interpreted standards through his versions and avant-gardist John Zorn has said that in his own way, Frank Sinatra was as much a jazz improviser as Charlie Parker.
- Nick Dedina

The resurgence of Tony Bennett to the top of the charts was one of the most gratifying surprises of the 1990s. Bennett was a (very big) cog in the Columbia hit machine of the ’50s and ’60s and he had to fight Mitch Miller tooth and nail to do the jazz albums and classy material he loved. He toured extensively with Duke Ellington and become the first white star to record with Count Basie. The cream of this era is collected on the exceptional Jazz, a compilation which also features Art Blakey, Stan Getz, and Bennett’s main ivory tinkler, Ralph Sharon. A few years after “I Left My Heart in San Francisco,” Bennett got knocked down during the acid rock wave of the late ’60s but he answered back with his own label, Improv and cut two great albums with Bill Evans. Always a warm and good-humored singer, age and experience took the brassy edge off Bennett’s voice and he decided to stick with jazz accompaniment. In the late ’80s he recorded with Dexter Gordon, Dizzy Gillespie and George Benson, and slowly rebuilt his base. The ’90s MTV generation took to Bennett’s music and his unruffled cool personality in a very big way. His music is timeless.
- Nick Dedina

Pat Metheny is one of the most bipolar of modern musicians, jumping from gentle Crossover Jazz with smooth synthesizers to wild Free Jazz explorations. Metheny is unafraid of taking chances. After a string of Latin-influenced, synth-heavy hits that filled concert halls, he released Zero Tolerance for Silence, an album featuring forty minutes of feedback noise. As a soloist, Metheny is among the top modern guitarists, using his lightly chorused electric guitar to play startlingly original chromatic lines with exceptionally tasteful phrasing. He has worked with countless artists, but collaborations with Jaco Pastorius, Herbie Hancock, Gary Burton and Ornette Coleman stand out as noteworthy. Metheny may also be responsible for fusing Heavy Metal and jazz — at least in terms of his hairstyle decisions.
- Jessy Terry

Long since gone, Lady Day still casts a spell. Like her musical alter ego, Frank Sinatra, interest in her personal life threatens to overshadow her importance to jazz and pop. Forget the tragedy, listen to the music. Holiday’s attention to phrasing has influenced generations of singers and players. With her trademark gardenia in her hair, she advanced the art of singing by adding personal nuance and detail to each number. She practiced a subtle craft, telling a story with each lyric…her story. But even if all you speak is Esperanto, she has enough musicianship to duet with the likes of Lester Young and Ben Webster. Like them, her music dazzles with emotion, not empty gymnastics.
- Nick Dedina