100 Greatest Men: #3. Willie Nelson

100 Greatest Men: The Complete List

He started out as an unconventional songwriter trying to be a conventional artist.  But when Willie Nelson let his hair down, he became a country legend for the ages.

Nelson was raised by his grandparents in Texas, who encouraged him to play the guitar and to write songs.  When his sister Bonnie married fiddle player Buddy Fletcher, Nelson joined his band as the frontman, staying with him until he graduated high school and did a brief stint in the Air Force.

Nelson’s next few years were a combination of performing local gigs, being a radio disc jockey, and cutting independent records, trying to secure a major recording contract.  Nelson sold his composition, “Family Bible”, which became a hit for Claude Gray in 1960.  This inspired Nelson to move to Nashville, where his unique vocal phrasing made being a recording artist a less promising path than songwriting.   While Nelson did have some moderate success as an artist on Liberty and then on RCA, it was his songwriting that paid the bills.  He scored major hits with Faron Young (“Hello Walls”), Patsy Cline (“Crazy”), and Roy Orbison (“Pretty Paper.”)

By the end of the sixties, Nelson was frustrated by the limitations of the Nashville approach.  He moved to Austin, Texas, where a younger music scene was hungry for country music with a rock and roll sensibility.  Nelson grew his hair out, embraced the counterculture movement, and started making music without limitations.  He released a series of concept albums for Atlantic which sold poorly at the time, but are now considered masterpieces.   When he moved to Columbia, he demanded creative control.  The label was not optimistic about Red-Headed Stranger, a sparsely arranged concept album, but his cover of “Blue Eyes Crying in the Rain” was a smash hit, and suddenly, Nelson was a superstar.

Though his songwriting was already legendary, Nelson was just as successful covering other artist’s work.  Throughout the seventies and most of the eighties, he was an international icon, having major country hits on his own and in collaboration with Waylon Jennings, Merle Haggard, Ray Price, Leon Russell, Ray Charles, and even Julio Iglesias.  Stardust, his collection of pop standards, sold millions and set a longevity record on the Country Albums chart. His cover of “Always on My Mind” sold more than two million copies in the United States alone.  He finished the eighties as the decade’s #1 singles artist.

The nineties brought a commercial downturn, but he regained his artistic footing with Across the Borderline, an acclaimed album from 1993, the same year he was inducted into the Country Music Hall of Fame. Freed from the expectations of country radio, Nelson continued to push boundaries, working with artists and producers from across the musical spectrum, and he remained one of country’s most popular and enduring touring acts.

The new century brought him back to the top of the charts with “Beer For My Horses”, a duet with Toby Keith that spent six weeks at #1.  He won a Grammy for his duet with Lee Ann Womack on “Mendocino County Line.”   Endlessly prolific, he has collaborated with everyone from Ryan Adams to Wynton Marsalis in recent years, and in 2014, released Band of Brothers, another critically acclaimed album that has more new Nelson compositions than anything else he’s released this century.  Now 80, Nelson continues to tour and record, adding to a legacy that has already made him one of the all-time greats.

Essential Singles:

• Blue Eyes Crying in the Rain, 1975
• Good Hearted Woman (with Waylon Jennings), 1975
• Mammas Don’t Let Your Babies Grow Up to be Cowboys (with Waylon Jennings), 1978
• Georgia on My Mind, 1978
• My Heroes Have Always Been Cowboys, 1980
• On the Road Again, 1980
• Angel Flying too Close to the Ground, 1981
• Always on My Mind, 1982
• Pancho and Lefty (with Merle Haggard), 1983
• City of New Orleans, 1984
• Seven Spanish Angels (with Ray Charles), 1984

Essential Songs:

• Family Bible (Claude Gray), 1960
• Hello Walls (Faron Young), 1961
• Funny How Time Slips Away (Billy Walker), 1961
• Crazy (Patsy Cline), 1961
• Three Days (Faron Young/k.d. lang), 1962/1989
• Night Life (Ray Price), 1963
• Pretty Paper (Roy Orbison), 1963
• Yesterday’s Wine (George Jones & Merle Haggard), 1982

Essential Albums:

• Yesterday’s Wine, 1971
• Shotgun Willie, 1973
• Phases and Stages, 1974
• Red Headed Stranger, 1975
• Stardust, 1978
• Across the Borderline, 1993
• Spirit, 1996
• Teatro, 1998
• Two Men with the Blues (with Wynton Marsalis), 2008

Next: #2. George Jones

Previous: #4. Johnny Cash

100 Greatest Men: The Complete List