© William P. Gottlieb Library of Congress

Lester Young & Billie Holiday

By Scott Yanow

“Billie Holiday loved the way that Lester Young played fills and harmonies behind her when she sang.”

Billie Holiday and Lester Young first met in 1934 and while they never had a romantic relationship, they were close friends, brother and sister, from the start and shared similar musical viewpoints.

Holiday had a small voice but she made every note count, expressing her emotions quite effectively in subtle ways and phrasing behind the beat. Young had a light floating tone, particularly compared to the pacesetter of the tenor Coleman Hawkins and, while he could play fast, he preferred to create pretty melodies. They also had complementary viewpoints on life, particularly in the early days.

Billie Holiday was born April 7, 1915 as Eleanora Fagan in Philadelphia and had a rough childhood. Her parents were never married and her father guitarist Clarence Holiday abandoned his family. Billie dropped out of school at 11, suffered through some harrowing episodes, but discovered jazz in the late 1920s through the recordings of Louis Armstrong and Bessie Smith.

She began to perform as a singer in nightclubs in 1929 when she was just 14, developing her own style. Producer John Hammond discovered her in 1933 and arranged for her to record two songs later that year with a pickup group led by Benny Goodman. While those records did not sell well, in 1935 Hammond signed her to the Brunswick label where she recorded with all-star groups led by Teddy Wilson. She also started recording in a similar format but as a leader starting later in 1936.

Lester Young was born Aug. 27, 1909 in Woodville, Mississippi. He freelanced for a few years, was with Walter Page’s Blue Devils in Kansas City in 1932 and joined Count Basie the following year. He played with Andy Kirk’s orchestra for six months but his very individual style was looked down upon and he was soon back with Basie’s band back in Kansas City. Lester Young was the band’s star soloist for the next five years. His tone and style fit in perfectly with the light but always-swinging Basie rhythm section.

Soon after Young and Holiday met, the tenor named her “Lady Day.” In return Holiday, who greatly admired President Franklin D. Roosevelt, named Young “President” which was soon shortened to Pres or Prez.

They had some opportunities to perform together in Harlem clubs, but the first time their musical partnership was documented was on her recording date with Teddy Wilson on Jan. 25, 1937. During the next 4 ½ years, they appeared together on 12 sessions, recording 45 songs (along with 26 alternate takes) that made musical history.

Five of the sessions were in 1937. It all began on Jan. 25 with the ironically titled “He Ain’t Got Rhythm,” a lightweight pop tune that they uplifted. However this session is best remembered for “This Year’s Kisses,” “Why Was I Born,” and particularly “I Must Have That Man.” Young’s very warm playing on the latter perfectly fit Lady Day’s singing which is full of yearning and optimism.

Teddy Wilson and his Orchestra
“I Must Have That Man”
January 25, 1937

Buck Clayton (tp), Benny Goodman (cl), Lester Young (ts), Teddy Wilson (p), Freddie Green (g), Walter Page (b), Jo Jones (d), Billie Holiday (vcl).

While the inclusion of Benny Goodman on that first date was a rarity (he was a rather busy bandleader during the era), having trumpeter Buck Clayton plus the Basie rhythm section (with Teddy Wilson on piano) was an inspiration. Clayton would be a bright spot on nine of the first ten Holiday-Young sessions. His understated power and sensitive playing were always strong assets.

The May 11, 1937 set is highlighted by two gems: “I’ll Get By” (a hit for Dick Haymes with Harry James several years later) and “Mean To Me” (a standard since the late 1920s). While those two songs would have long histories and other memorable recordings, the interplay between the singer and the tenor on this session is particularly memorable, although altoist Johnny Hodges’ beautiful solo on the former practically steals the show.

The music from June 1, 1937 (with clarinetist Buster Bailey) is particularly joyful, especially “Easy Living” and “Foolin’ Myself.” The mood carries over to the June 18, 1937 set which includes “A Sailboat In The Moonlight,” “Without Your Love,” and the somewhat exuberant “Me, Myself And I.” These two sessions are a reminder of how happy Billie Holiday often sounded during the era.

This was a period when Lady Day and Pres were performing together on a nightly basis as members of the Count Basie Orchestra. Unfortunately, Holiday’s recording contract was with Vocalion/Brunswick while Basie was with Decca so they could not record together. All that exists of her period with Basie are two vocals from radio broadcasts (“They Can’t Take That Away From Me” and Swing, Brother, Swing”), neither of which feature Young.

Holiday, Young, Clayton, Bailey and the Basie rhythm section (with pianist Claude Thornhill) met up again on Sept. 13, 1937 with “He’s Funny That Way” and “Getting Some Fun Out Of Life” taking honors.

However the Jan. 6, 1938 session, with trombonist Benny Morton in Bailey’s place and Teddy Wilson back on piano, was difficult to beat. “My First Impression Of You” is somewhat forgettable but a medium-slow “I Can’t Believe That You’re In Love With Me,” “If Dreams Come True,” and particularly “When You’re Smiling” are gems. The latter, which has a wonderful tenor solo, could have gone on far past the three-minutes of the 78. Young’s chorus is a classic and one could imagine Lady Day returning for more.

Teddy Wilson and his Orchestra
“When You’re Smiling”
January 6, 1938

Buck Clayton (tp), Benny Morton (tb), Lester Young (ts), Teddy Wilson (p), Freddie Green (g), Walter Page (b), Jo Jones (d), Billie Holiday (vcl).

The same lineup returned on Jan. 27, 1938 for pleasing renditions of “Now They Call It Swing,” “Back In Your Own Backyard,” “On The Sentimental Side,” and “When A Woman Loves A Man.” Here, as on the other sessions, the Holiday-Young combination results in some magical moments.

Billie Holiday spent much of 1938 singing with Artie Shaw’s increasingly popular orchestra. Once again she and the bandleader were signed to different labels so only one title, “Any Old Time” which was quickly withdrawn, resulted from their collaboration.

On Sept. 16, 1938 Holiday was ready to sing with Young and the other Basie sidemen again (including trombonist Dickie Wells) and, while no classic resulted (“The Very Thought Of You” with Young on clarinet is best), one can imagine that she enjoyed the reunion. The two titles from Oct. 31 with a larger group that included six horns counting Young, is less eventful.

Surprisingly at this point in time, although Billie Holiday continued recording regularly and Lester Young stayed busy with Basie, there were only three more joint recording sessions; one apiece in 1939, 1940 and 1941. Lady Day was becoming a star and her newer records, while still jazz-oriented, often had little solo space for her sidemen.

For her Dec. 13, 1939 session, she uses a nonet from the Basie band (other than pianist Joe Sullivan) and Young was a minor figure on such numbers as “Night And Day” and “The Man I Love.” The June 7, 1940 date with Roy Eldridge and four saxophonists including Young was better, particularly “Laughing At Life.” But the Mar. 21, 1941 set in which Young is part of a septet led by pianist Eddie Heywood is best.

On “All Of Me,” Lady Day and Pres bring back their old musical magic and create their final classic recording.

Billie Holiday with Eddie Heywood Orchestra
“All Of Me”
March 21, 1941

Shad Collins (tp), Leslie Johnakins, Eddie Barefield (as), Lester Young (ts), Eddie Heywood (p), John Collins (g), Ted Sturgis (b), Kenny Clarke (d), Billie Holiday (vcl).

Billie Holiday and Lester Young soon drifted apart. When Young left the Basie band in 1941, he was featured with a septet that he co-led with his brother drummer Lee Young. Billie Holiday was a guest on their radio broadcast of June 1, 1942, but that band was never a success.

Young had a mostly happy second period with the Basie band during 1943-44 before being drafted and having a horrifying experience in the Army. After his discharge in 1945, he often played quite well but his state of mind was not the best and he became an alcoholic.

While Billie Holiday’s singing on her Decca recordings of the 1940s was some of the best of her career, her personal life was challenging and she spent a year in jail due to her drug problems. Pres did not care for the type of men who Holiday was choosing as her boyfriends and he was disturbed by her drug use and heroin addiction. While few details are known about their disagreements, their friendship was strained and they did not even see each other at all for three years in the early 1950s.

They did gradually overcome their differences. Young sat in with Lady Day at the 1954 Newport Jazz Festival and on May 6, 1955 they appeared together at a Basie reunion concert at Carnegie Hall.

At the time of the famous Sound Of Jazz telecast of Dec. 8, 1957, Lester Young was in bad physical shape, barely able to stand up. He was supposed to be featured on several of the numbers during the show but was only able to solo on one, not wanting to pass up playing “Fine And Mellow” with Billie Holiday.

While there were solos by the likes of Coleman Hawkins, Ben Webster, Gerry Mulligan, Vic Dickenson and Roy Eldridge and heartfelt singing by Lady Day, Young’s single chorus provided the most touching moments as Holiday looked on and seemed to be thinking about the mutual love they felt and their many shared experiences.