The New York Times described him as an "influential band leader" whose "suave bass-baritone" and "full-throated, sugary approach to popular songs inspired singers such as Earl Coleman, Johnny Hartman, Joe Williams, Arthur Prysock, and Lou Rawls.

[8][10][11] Heading to Chicago, Illinois, Eckstine joined Earl Hines' Grand Terrace Orchestra in 1939, staying with the band as vocalist and trumpeter until 1943.

In 1944, Eckstine formed his own big band,[4] and it became the finishing school for adventurous young musicians who would shape the future of jazz including Charlie Parker, Dizzy Gillespie, Dexter Gordon, Gene Ammons, Miles Davis, Art Blakey, Cecil Payne, Fats Navarro, Lucky Thompson, John Malachi, Sarah Vaughan, Pearl Bailey, and Lena Horne.

[4] The Billy Eckstine Orchestra is considered to be the first bebop big-band,[4] and had Top Ten chart entries that included "A Cottage for Sale" and "Prisoner of Love".

[4] He signed with the newly established MGM Records, and had immediate hits with revivals of "Everything I Have Is Yours" (1947), Rodgers and Hart's "Blue Moon" (1948), and Juan Tizol's "Caravan" (1949).

Eckstine had further success in 1950 with Victor Young's theme song to "My Foolish Heart", and the next year with a revival of the 1931 Bing Crosby hit, "I Apologize".

[17] One photograph taken by Holmes and published in Life showed Eckstine with a group of white female admirers, one of whom had her hand on his shoulder and her head on his chest while she was laughing.

Eckstine's biographer, Cary Ginell, wrote of the image that Holmes "...captured a moment of shared exuberance, joy, and affection, unblemished by racial tension".

Tony Bennett would recall that "It changed everything...Before that, he had a tremendous following...and it just offended the white community", a sentiment shared by pianist Billy Taylor who said that the "coverage and that picture just slammed the door shut for him".

[22] In 1951, Eckstine performed at the seventh Cavalcade of Jazz concert held on July 8 at Wrigley Field in Los Angeles, produced by Leon Hefflin, Sr. Also featured were Lionel Hampton and his Revue, Percy Mayfield, Jimmy Witherspoon, Joe Liggins and The Honeydrippers and Roy Brown.

[1] The 1960 Las Vegas live album, No Cover, No Minimum, featured Eckstine taking a few trumpet solos and showcasing his nightclub act.

[26] A State Historical Marker was placed at 5913 Bryant Street in Pittsburgh's Highland Park neighborhood to mark the house where Eckstine grew up.

[27][28] His friend Duke Ellington recalled Eckstine's artistry in his 1973 autobiography Music is My Mistress: Eckstine-style love songs opened new lines of communication for the man in the man-woman merry-go-round, and blues a la B were the essence of cool.

... His style and technique have been extensively copied by some of the neocommercial singers, but despite their efforts, he remains out front to show how and what should have been done.Sammy Davis Jr. made several live appearances and impersonated Eckstine.

I wanted to dress like him, talk like him, pattern my whole life as a musician and as a complete person in the image of dignity that he projected.... As a black man, Eckstine was not immune to the prejudice that characterized the 1950s.