Long before I knew who Willie Nelson even was, I was listening to the music he wrote. Pretty Paper was a hit for Roy Orbison in 1963. On The Supremes Sing Country, Western & Pop (1965), they covered Funny How Time Slips Away.
Of course, the big hit was Crazy by Patsy Cline which went to #2 on the Adult Contemporary charts in 1961 and #2 on the country charts early the next year. More significantly for, it hit #9 on the pop charts in 1961, and was covered by Linda Ronstadt (#6 country in 1977).
I don’t know when I was first aware of Nelson as a performer. He was the “outlaw” country star who owed money to the IRS due to bad management and who got arrested several times for marijuana possession.
I do know the first album of his that I bought was Across the Borderline (1993), produced by Don Was, Paul Simon, and Roy Halee. It features songs by Simon, Ry Cooder, John Hiatt, Bob Dylan, Lyle Lovett, and Nelson. It features songs such as Getting Over You, a duet with Bonnie Raitt; and Peter Gabriel’s Don’t Give Up, a duet with Sinead O’Connor.
I thought that his 40th album would be a commercial pop breakthrough. For a while, it was out of print, but it’s currently available as an add-on from Amazon for five bucks.
Subsequently, I got other Nelson albums, including his hit, Red Headed Stranger (1975). I know at least one work colleague who simply cannot stand his voice, but I’ve grown to enjoy it.
Crazy – Patsy Cline
Crazy – Willie Nelson
Crazy – Linda Ronstadt
Pretty Paper – Roy Orbison, #10 adult contemporary, #15 pop, #27 on the Christmas singles chart in 1963
Pretty Paper – Willie Nelson, 1964
Funny How Time Slips Away – Willie Nelson
Funny How Time Slips Away – Supremes
She’s Not for You, #43 country in 1965
Blue Eyes Crying in the Rain, #1 country, 21 pop in 1975
On the Road Again, #1 country, #7 adult contemporary, #20 pop in 1980
Always on My Mind, #1 country, #2 adult contemporary, #5 in 1985
Still is Still Moving to Me, single that failed to chart in 1993
American Tune, a duet with Simon, #70 pop in 1993
Something You Get Through, 2018
Coverville 1214: The Willie Nelson Cover Story III