[Ed. note: This post was originally published on March 24, 2015]
Billie Holiday and Ben Webster were lovers for a brief stretch in the mid-’30s. A classic photograph taken by the Danish jazz fan Timme Rosenkrantz behind the Apollo in 1935 pictures them together, but in between the playful pettin’ and pokin’, there was at least one instance of the brutality that occurred all too often in Billie’s life. Ben gave her a black eye, and a day or two later when he arrived to pick her up for a date, her mother attacked him with an umbrella in retribution. “Naturally I could see that Billie’s Ma was real mad,” reflected the great tenorman. “But what made it worse was that Billie was just bursting with laughter at the sight of me being whipped. That made me mad, but we all ended up as friends.”
Ben’s mother also played a role in the demise of the fling. When he brought Lady Day home to Kansas City to meet Mrs. Webster and his great aunt, they found her insufficiently lady-like for a prospective daughter-in-law. Nonetheless, some of Ben’s finest playing of the mid-‘30s– before his style completely matured under the influence of his Ellington section-mate Johnny Hodges in the early ’40s– took place on a handful of sessions he appeared on with Billie between 1935 and ‘38.
Billie later remarked in Lady Sings the Blues, “Roy Eldridge, Lester Young, Benny Webster—they were all friends of mine.” The friendship revived in musical settings 20 years after they’d first met. Billie often sat in with Ben when he was playing Chicago clubs in the mid-’50s, and he was in the combo that backed Billie on her 1956 session, All Or Nothing At All. The following year, he played the first solo on the classic performance of “Fine and Mellow” that Billie sang on the television special, The Sound of Jazz. It’s a performance renowned for Lester Young’s 12-bar solo, a veritable swan song for the saxophonist, who like Billie died two years later. But Webster is in expressive, full-throated form as he sets the tone for the series of solos by the all-stars gathered around the Lady who was highly regarded as a full peer of these great players.
Ben provided just the right measure of accompaniment on All Or Nothing At All, which is Billie’s most coherent and successful date from the latter part of her career. As Webster’s biographer Frank Buchman-Moller described it, “The listener catches the feeling that all the musicians are devoted to Holiday…No one seeks exposure at the expense of the others; all function as a homogeneous group…Ben is particularly considerate in his obligattos, never getting in the way, but always keeping his velvet tone under her voice and thus helping carry her forth. He is equally considerate in his solos, never using growl in fast tempi, probably feeling it would be overpowering in comparison to Holiday’s fragile voice…[Trumpeter Harry “Sweets”] Edison and especially Ben challenge her wonderfully and congenially.”
