Before pursuing acting more intensely, Eastwood released his debut album Cowboy Favorites in 1959, a collection of covers, including Cole Porter’s “Don’t Fence Me In” and Bob Wills’ “San Antonio Rose.” The album featured Eastwood’s renditions of some cowboy classics linked to his role as Rowdy Yates in the hit Western TV series Rawhide.
In tandem with his legendary acting career, Eastwood also went on to score numerous films, including The Bridges of Madison County, Flags of Our Fathers, Million Dollar Baby, Grace Is Gone, Changeling, Hereafter, J. Edgar, Mystic River, and Gran Torino, along with the original piano music for In the Line of Fire.
A lifelong lover of music, in 2008 Eastwood was a guest on the iTunes Celebrity Playlist Podcast and shared some of his all-time favorite songs.
His favorites (see full list below) are plentiful, spanning Joe Williams, Duke Ellington, Dinah Washington, and more from the big band and jazz era, along with a few songs he wrote and some contemporary picks like British singer Jamie Cullum and South African band Overtone.
Here’s a deeper look into just five songs Eastwood revealed as all-time favorites, and what he had to say about some of them.
1. “A Tisket, A Tasket,” Elle Fitzgerald (1938)
Written by Ella Fitzgerald and Al Feldman
Dinah Washington, Peggy Lee, Irene Kral, and Diana Krall were the aritsts Eastwood named as his favorite female singers, along with Ella Fitzgerald.
In 1938, Fitzgerald reimagined the 19th-century children’s song “A Tisket, A Tasket” along with composer and musician Al Feldman (later known as Van Alexander). Both transformed the children’s song into a jazz piece, and it became a breakout hit for Fitzgerald and the Chick Webb Orchestra, as well as a jazz standard.
Dating back to 1879, the earliest version of “A Tisket, A Tasket” was composed as a children’s rhyming game, which was sung as kids danced in a circle. Another child would run outside of the circle and drop a handkerchief. The child nearest would pick it up and have to chase the kid who dropped it. If they were caught, the dropper would either have to join the circle, get a kiss, or reveal who they liked.
For her version, Fitzgerald changed the color of the basket from green and yellow to brown and yellow. In her rendition, a girl picks up the basket that is left on the ground. Fitzgerald and Webb also released a follow-up to the song in 1938 called “I Found My Yellow Basket.”
“Just about anything by Ella Fitzgerald,” said Eastwood of one of his favorites. “One of the greatest pop singers ever starting out with ‘A-Tisket, A-Tasket,’ which was her first hit when she was a teenager, and then she went on to be one of the greatest singers ever.”
A brown and yellow basket
I send a letter to my mommy
On the way I dropped it
I dropped it, I dropped it
Yes, on the way I dropped it
A little girlie picked it up
And put it in her pocket
Read the fuller meaning behind the children’s classic “A Tisket, A Tasket” HERE.
2. “Nature Boy,” Nat King Cole (1948)
Written by Eden Ahbez
Calling him one of the finest singers of his generation, Eastwood said he felt fortunate to grow up in a time when Nat King Cole was around. “I feel lucky to have been raised in a generation that had King Cole and Frank Sinatra as our two most popular singers of that era,” said Eastwood. “His [Cole’s] unforgettable ‘Mona Lisa.’ He could make anything, even ‘Nature Boy,’ any type of song he could interpret and make it great.”
Eden Ahbez, an unkempt beatnik poet and one of the earliest figures in the hippie movement, originally approached Cole backstage with a song he wrote for him called “Nature Boy.” Famously known for living under the Hollywood sign in Griffith Park in Los Angeles, and surviving on fruits, nuts, and vegetables, Ahbez had to be tracked down before Cole could record the song.
When released, “Nature Boy” shot to No. 1 on the Billboard Hot 100 and No. 2 on the R&B chart.
There was a boy
A very strange enchanted boy
They say he wandered very far
Over land and sea
A little shy
And sad of eye
But very wise was he
And then one day
One magic day he passed my way
And while we spoken of many things
Fools and kings
This he said to me
The greatest thing
You’ll ever learn
Is just to love
And be loved in return
Read the meaning behind Nat King Cole’s “Nature Boy” HERE.
3. “Summer Wind,” Frank Sinatra (1965)
Written by Heinz Meier and Hans Bradtke; translated by Johnny Mercer
Translated into English by Johnny Mercer and released by Frank Sinatra in 1965, “Summer Wind” was originally written by Heinz Meier and Hans Bradtke and released in Germany as “Der Sommerwind.” The song, which appears on Sinatra’s album Strangers In The Night, centers around a love that blew away, like the wind—Like painted kites, those days and nights, they went flyin’ by / The world was new beneath a blue umbrella sky.
Sinatra’s version hit No. 1 on the Billboard Easy Listening chart.
In 2021, Stephen Colbert asked Bruce Springsteen to name the one song he’d listen to for the rest of his life, and he said Sinatra’s “Summer Wind.”
On his list, Eastwood also included Sinatra’s 1958 No. 1 hit “Come Fly with Me.”
The summer wind, came blowin’ in from across the sea
It lingered there to touch your hair and walk with me
All summer long we sang a song and then we strolled that golden sand
Two sweethearts and the summer wind
Like painted kites, those days and nights, they went flyin’ by
The world was new beneath a blue umbrella sky
Then softer than a piper man one day it called to you
I lost you, I lost you to the summer wind
4. “Is That All There Is?” Peggy Lee (1969)
Written by Jerry Leiber and Mike Stoller
Is that all there is? sings Peggy Lee on her 1969 hit “Is That All There Is?” If that’s all there is my friends / Then let’s keep dancing / Let’s break out the booze and have a ball / If that’s all there is.
Originally written by the songwriting duo of Jerry Leiber and Mike Stoller as a song of disillusionment, Lee’s delivery of the song is a more empowered communiqué on living life to its fullest.
The song hit No. 1 on the Billboard Easy Listening chart and peaked at No. 11 on the Hot 100 for Lee and has been covered by Chaka Khan, PJ Harvey, and Alan Price among many more.
And then I fell in love
With the most wonderful boy in the world
We’d take long walks by the river or
Just sit for hours gazing into each other’s eyes
We were so very much in love
Then one day
He went away
And I thought I’d die, but I didn’t
And when I didn’t
I said to myself
Is that all there is to love?
5. “Why Should I Care?” Diana Krall (1999)
Written by Clint Eastwood, Linda Thompson, Carole Bayer Sager
Eastwood listed two songs by Diana Krall on his favorites list, including her cover of “Midnight Sun,” featured in the 1997 film Midnight in the Garden of Good and Evil. The song was originally written by Sonny Burke, Lionel Hampton, and Johnny Mercer and first released in 1948 by Lionel Hampton and His Orchestra.
His second Krall pick was one he actually co-wrote, “Why Should I Care,” a hidden piano-led track featured on her fifth album, When I Look in Your Eyes. Krall’s jazz-fused album also won two Grammys for Best Jazz Vocal and Best Engineered Album, Non-Classical.
“Her interpretation of ‘Midnight Sun,’ and ‘Why Should I Care?’—I happen to know the writer of that one,” joked Eastwood, who co-wrote the latter track with Linda Thompson and Burt Bacharach‘s former songwriting partner and wife Carole Bayer Sager. “But anyway, ‘Midnight Sun’ [written by] Johnny Mercer, one of the great, probably the greatest song lyricists ever, even to this day.”
Eastwood also listed two more songs by Lee on his list, her 1942 song “Why Don’t You Do Right” and her signature song “Fever.”
Was there something more I could have done?
Or was I not meant to be the one?
WhereÂ´s the life I thought we would share?
And should I care?
And will someone else get more of you?
Will she go to sleep more sure of you?
Will she wake up knowing you’re still there?
And why should I care?
Clint Eastwood’s Full List of Favorite Songs:
- Louis Jordan – “Nobody Here But Us Chickens”
- Louis Jordan – “Saturday Night Fish Fry”
- Louis Jordan – “Run Joe”
- Louis Jordan – “Five Guys Named Moe”
- Duke Ellington – “The the “A” Train”
- Louis Armstrong & Duke Ellington – “I’m Just a Lucky So and So”
- Erroll Garner – “Misty”
- Diana Krall – “Midnight Sun”
- Diana Krall – “Why Should I Care?”
- Peggy Lee – “Why Don’t You Do Right”
- Peggy Lee – “Fever”
- Peggy Lee – “Is That All There Is?”
- Jamie Cullum – “Grace Is Gone” (co-written by Clint Eastwood, Grace is Gone soundtack)
- Jamie Cullum – “Gran Torino” (co-written by Clint Eastwood, Gran Torino soundtrack)
- Overtone and Yollandi Nortjie – “9000 Days” (co-written by Clint Eastwood, Invictus soundtrack)
- Johnny Hartman – “I See Your Face Before Me”
- Joe Williams – “If I Should Lose You”
- Joe Williams – “What’s New”
- Woody Herman & His Orchestra – “Lemon Drop”
- Woody Herman & His Orchestra – “Early Autumn”
- Dinah Washington – “What Difference a Day Makes”
- Ella Fitzgerald – “A-Tisket, A-Tasket”
- Irene Kral – “Better Than Anything”
- Irene Kral – “This Is Always”
- Irene Kral – “It’s a Wonderful World”
- Jimmy Durante – “September Song”
- Nat King Cole – “Mona Lisa”
- Nat King Cole – “Nature Boy”
- Frank Sinatra – “Summer Wind”
- Frank Sinatra – “Come Fly With Me”
- Billy Ward and his Dominoes – “Sixty Minute Man”
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