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8 Great Country Covers By Willie Nelson’s Old Friend, Frank Sinatra

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As exciting as it may be to get yet another new Willie Nelson album, it’s not totally out of the blue for the Red-Headed Stranger to cover the music of Frank Sinatra. Two years after the release of Summertime: Willie Nelson Sings Gershwin, one of the most iconic living song interpreters lends his voice to My Way, a covers album issued on Sept. 14 by Legacy Recordings. It’s anchored by versions of “Fly Me to the Moon,” “Summer Wind,” “It Was a Very Good Year,” “A Foggy Day,” “One For My Baby (and One More For the Road),” “Night and Day,” “I’ll Be Around,” “Young at Heart,” a duet version of “What is This Thing Called Love” featuring Norah Jones and other easy listening standards. It offers a nice change of pace for Nelson, but it’s nothing completely new for the creative force behind Stardust, a 1978 roundup of American standards.

By all means, the “Blue Moon” beyond the one in Kentucky and the music of Ol’ Blue Eyes’ Rat Pack running buddy and Reprise Records co-founder Dean Martin will always impact well-rounded entertainers in the country music genre, from Nelson to such social media age stars as Blake Shelton, Luke Bryan and Brett Eldredge. What’s way more moving is the rare chance to hear Sinatra, a noted fan of fellow vocal talents Eddy Arnold and George Jones, cover famous country songs. In these eight instances, Sinatra stepped away from the catalogs of Ira Gershwin, Cole Porter, Johnny Mercer and other pop wordsmiths to do more than just try his hand at the occasional Hank Williams or Elvis Presley tribute or add a little twang to “I’ve Got You Under My Skin,” “Michael & Peter” or “I’m Gonna Live Here Til I Die.”

“That’s How Much I Love You” (Eddy Arnold)

Long before Arnold’s sweet yet commanding voice suited the Nashville sound in the ’60s, he took this 1946 co-write with Oak Ridge Boys co-founder Wally Fowler to the top five. One year later, Sinatra added a little jazz-pop swing to a country and Western hit.

“You Are My Sunshine” (Jimmie Davis)

In time, this song became a standard in the English-speaking world on par with the works of Sinatra or Bing Crosby. It started out as a country song by the future governor of Louisiana, long before Ray Charles earmarked its page in the great American songbook.

“Like a Sad Song” (John Denver)

However you may feel about Denver’s country credentials, he was a fine mainstream ambassador of rural storytelling. Denver’s gorgeous orchestral pop composition “Like a Sad Song” might not be driven by pedal steel, but Sinatra’s version sounds more “country” than other selections on this list. Shoot, it might be the second best country song in the family’s repertoire behind daughter Nancy’s Lee Hazlewood duet “Summer Wine.”

“Ode to Billie Joe” (Bobbie Gentry)

In the age of variety television, Sinatra couldn’t resist covering Gentry’s groundbreaking hit with special guest Ella Fitzgerald. It’s more a case of a Las Vegas showman tipping his fedora to a pop starlet than a traditional country cover.

“I Can’t Stop Loving You” (Don Gibson)

This song that now belongs to the entire world started out in the country music genre. Gibson’s original version debuted as one of the most important B-sides in pop music history. It sneaked into the mainstream as the flipside to another ever present classic, “Oh, Lonesome Me.”

“Gentle on My Mind” (John Hartford)

Seemingly every crooner in Hollywood, Chicago and New York City tried building on the success of this Glen Campbell classic, written by a quirky yet brilliant bluegrass picker. Sinatra turned what we’d now consider a singer-songwriter hit into a gorgeous example of orchestral pop. Under pretty much any circumstance, this is a near-perfect pop song that belongs on the next golden disc that NASA launches into outer space.

“Nobody Wins” (Kris Kristofferson)

Getting the feeling yet that Sinatra just picked great songs, regardless of their original genre? Gifted vocalists from Sinatra to the genre-defiant Ronnie Milsap excelled when tackling music and words by one of the best songwriters to ever hail from Nashville.

“By the Time I Get to Phoenix” (Jimmy Webb)

Campbell’s run as “the man” came in part because of his working relationship with Webb. One of his more crooner-friendly hits fit Sinatra’s style like a fitted three-piece suit on 1968’s Cycles, an album that also features a cover of Bobby Russell’s “Little Green Apples.”

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8 Great Country Covers By Willie Nelson’s Old Friend, Frank Sinatra