Favorite Billie Holiday Songs

I love listening to Billie Holiday, there is something magical about her songs that take one back down a nostalgic trip to another time and place. I discovered her while in college and have a large collection of her albums. In my opinion there are three leaders of song who stand above all others – Billie Holiday, Ella Fitzgerald, and Sarah Vaughan.

Billie Holiday (1915-1955) is one of the greatest and most influential singers of all time, according to Downbeat, Billboard, Esquire, Rolling Stone, and NPR. Frank Sinatra said ”Lady Day is the most important influence on American popular singing.” She won four Grammys and has been inducted into the Grammy Hall of Fame, Jazz Hall of Fame, Rock and Roll Hall of Fame, Down Beat Hall of Fame, and ASCSP Wall of Fame.

The Very Thought Of You by Billie Holiday

All Of Me by Billie Holiday

Billie Holiday had a tough life but she achieved success by her talent and hard work to become a leading singer in America. She was the most popular, highly awarded, and highly paid jazz singer in the world, on stage, radio, recordings, and movies in the 1930s and 1940s. Holiday broke new ground when working with Artie Shaw, she became one of the first female African American vocalists to work with an all-white orchestra. She gave three concerts at Carnegie Hall which was a great honor at that time.

Holiday performed with Teddy Wilson, Louis Armstrong, Duke Ellington, Count Basie, Glen Grey, Benny Goodman, Artie Shaw, Fred Astaire, Paul Whiteman, Oscar Peterson, Benny Carter, and many others.

Her life was destroyed by a vicious, racist attack on her by the U.S. federal government. She was persecuted for being outspoken about racism and civil rights in the U.S. and for her song Strange Fruit about the lynchings of blacks. Holiday was broken and turned to drugs. She was sent to prison. She died young at only 44 years old.

Blue Moon by Billie Holiday with Oscar Peterson, Ray Brown, and Barney Kessel.

I Can’t Give You Anything But Love by Billie Holiday with Teddy Wilson, Ben Webster, and Benny Goodman.

Once I was at a roadside diner and a Billie Holiday song started playing. I was mezmerized, lost in thought. I looked up and every single person in the diner was caught up in the song. Inspired I wrote this poem at the diner.

A Billie Holiday Song

By Bruce J. Wood

“I’ll be seeing you, in all the old familiar places,
that this heart of mine embraces,
all day through.”

“This was our song”, said the old lady at the
table next to mine, at my favorite roadside
diner. I looked at her and nodded.

“In that small café, the park across the way,
The children’s carousel, the chestnut tree,
the wishing well.”

“It was playing when we said goodbye.”
She said, holding her coffee cup up to her cheek.
“We danced close with our eyes closed.”

“I’ll be seeing you, in every lovely summer’s day,
In everything that’s light and gay,
I’ll always think of you that way.”

She went on, “That’s the last thing he said
to me – I’ll be seeing you – just like the song
– our song!”

“I’ll find you in the morning sun,
and when the night is new,
I’ll be looking at the moon,
but I’ll be seeing you.”

The diner quieted, everyone stopped to listen.
“You see, I drove him to the train station that day;
he was being shipped out to fight in World War Two.

He wrote—but was killed in a battle in Sicily.”
When she left, everyone’s heart followed
her out the door to the silent street.

I’ll Be Seeing You by Billie Holiday

Love Is Here to Stay by Billie Holiday

There have been two major motion pictures about her life. The biographical film Lady Sings the Blues was released in 1972 and was nominated for five Academy Awards, including Diana Ross for Best Actress. Another film, The United States vs. Billie Holiday, starred Andra Day and was released in 2021. Day was nominated for the Academy Award and won a Golden Globe.

Billie Holiday | Spotify