The Top 5 Songs That Clint Eastwood Loves

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Clint Eastwood began playing the piano when he was young and was jazz-obsessed. He absorbed it, along with blues, classical, and country music.

In 1959, Eastwood released his debut album Cowboy Favorites, a collection of covers that included Cole Porter’s “Don’t Fence Me In” and Bob Wills’ “San Antonio Rose.” This was before he focused more on acting. A few cowboy classics related to Eastwood’s portrayal as Rowdy Yates in the popular Western TV series Rawhide were included on the album.

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

Along with Ella Fitzgerald, Eastwood listed Dinah Washington, Peggy Lee, Irene Kral, and Diana Krall as his favorite female vocalists.

Together with pianist and composer Al Feldman (later known as Van Alexander), Fitzgerald reworked the 19th-century children’s song “A Tisket, A Tasket” in 1938. Both turned the children’s song into a jazz composition, and it went on to become a jazz standard as well as a breakthrough hit for Fitzgerald and the Chick Webb Orchestra.

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.”

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.”

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Eden Ahbez, a scruffy poet and pioneer of the hippie movement, first approached Cole backstage with a song he had written for him called “Nature Boy.” Before Cole could record the song, Ahbez had to be located because of his notoriety for subsisting on fruits, nuts, and vegetables while residing under the Hollywood sign in Griffith Park in Los Angeles.

When released, “Nature Boy” shot to No. 1 on the Billboard Hot 100 and No. 2 on the R&B chart.

3. “Summer Wind,” Frank Sinatra (1965) Written by Heinz Meier and Hans Bradtke; translated by Johnny Mercer

“Summer Wind,” originally composed by Heinz Meier and Hans Bradtke and released in Germany as “Der Sommerwind,” was translated into English by Johnny Mercer and performed by Frank Sinatra in 1965. On Sinatra’s album Strangers In The Night, the song focuses on a love that vanished with 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.”

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.

5. “Why Should I Care?” Diana Krall (1999) Written by Clint Eastwood, Linda Thompson, Carole Bayer Sager

On his list of favorite songs, Eastwood included two by Diana Krall, including her rendition of “Midnight Sun,” which was used in the 1997 movie Midnight in the Garden of Good and Evil. Sonny Burke, Lionel Hampton, and Johnny Mercer co-wrote the song’s original lyrics, which were initially performed by Lionel Hampton & His Orchestra in 1948. His second choice for Krall was “Why Should I Care,” a hidden piano-led piece on her fifth album, When I Look in Your Eyes, which he actually co-wrote. Two Grammy Awards for Best Jazz Vocal and Best Engineered record, Non-Classical went to Krall’s jazz-infused record.

“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.”

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