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The essential Willie Nelson playlist

Known as the Red-Headed Stranger, a serious cannabis enthusiast and one of country music's most iconic songwriters, Willie Nelson has recorded an incredible number of classic songs in his more than 60-year-long career in the industry. Just before the 2019 Grammy Awards, set for Feb. 10, Nelson will be honored by the Recording Academy's Producers & Engineers Wing for his musical achievements across dozens of records, hundreds of songs and at least six decades. 

Flip through the gallery for an essential playlist of Nelson's finest songs, from his cover of "Georgia On My Mind" to the quintessential "Whiskey River." 

 
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"If You've Got The Money, I've Got The Time"

"If You've Got The Money, I've Got The Time"
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Both Nelson and singer Lefty Frizzell scored No. 1 hits with “If You’ve Got The Money I’ve Got The Time,” 26 years apart from each other. It’s since become widely associated with Nelson, who released it in 1976. 

 
2 of 22

"Angel Flying Too Close To The Ground"

"Angel Flying Too Close To The Ground"
Doug Griffin/Toronto Star via Getty Images

Alongside his starring role in 1980’s "Honeysuckle Rose," Nelson also charted multiple No. 1 hits in songs from the Sydney Pollack film. It may not have the same popularity as “On The Road Again,” which also appears in "Honeysuckle Rose," but “Angel Flying Too Close To The Ground” is still a stunning example of Nelson’s songwriting. 

 
3 of 22

"Funny How Time Slips Away"

"Funny How Time Slips Away"
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Recorded in 1961 by Billy Walker and later a concert staple for Nelson, “Funny How Time Slips Away” continues the tradition of Nelson’s most iconic hits as a songwriter being recorded first (and after!) by other artists. In the years following its debut, Elvis Presley, Al Green, George Jones, The Supremes and more artists released their own versions of this somber, sad love song. 

 
4 of 22

"Night Life"

"Night Life"
Michael Ochs Archives/Getty Images

Originally sold to a Houston guitar picker named Paul Buskirk for just $150, the first recording of “Night Life” was rejected by Nelson’s label for not being “country” enough. Two years after it was written, Ray Price (with whom Nelson had toured frequently) scored a hit with the song in 1960. 

 
5 of 22

"Georgia On My Mind"

"Georgia On My Mind"
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Eighteen years after Ray Charles made “Georgia On My Mind” a No. 1 hit, Nelson proved that lightning sometimes strikes twice with his own version of this tribute to the Peach State. Even though he’s a Texas native, Nelson hit No. 1 on the Billboard country singles chart and won a Grammy for his cover. 

 
6 of 22

"My Heroes Have Always Been Cowboys"

"My Heroes Have Always Been Cowboys"
Michael Ochs Archives/Getty Images

“My Heroes Have Always Been Cowboys” was first recorded by Nelson’s friend and frequent collaborator Waylon Jennings in 1976, but Nelson scored his fifth No. 1 hit with the classic track, written by Sharon Vaughn. 

 
7 of 22

"Sad Songs and Waltzes"

"Sad Songs and Waltzes"
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Appearing on 1973’s "Shotgun Willie," “Sad Songs and Waltzes” is an ode to the eternal struggle of a heartbroken songwriter. According to the forlorn narrator on this Nelson ballad, “Sad Songs and Waltzes,” the kind of morose tunes that could be written about his former flame, just weren’t easy for a writer to sell to the Nashville publishing houses. 

 
8 of 22

"Mr. Record Man"

"Mr. Record Man"
Michael Ochs Archives/Getty Images

Nelson wrote "Mr. Record Man" during a time when he’d been forced to leave Nashville to figure out his financial situation, long before he was ever a country music icon. When his debut album "...And Then I Wrote" was released in 1962, though, Nelson’s trajectory changed dramatically — he got a deal with Liberty Records and soon became one of Music City’s most prominent songwriters. 

 
9 of 22

"Crazy"

"Crazy"
Photo by David Redfern/Redferns/Getty Images

This Patsy Cline classic was penned by Nelson in 1961, when he wasn’t yet a country superstar, and his own version of “Crazy” was included on his debut album, "...And Then I Wrote." Later, Nelson would say that Cline’s recording of “Crazy” was his favorite of any artist’s take on his songs. 

 
10 of 22

"Pretty Paper"

"Pretty Paper"
Michael Ochs Archives/Getty Images

Lonesome Christmas songs are much more common than they used to be, but none could ever approach the simple sadness of “Pretty Paper,” which tells the true tale of a street vendor with a spinal disorder known for selling pencils and paper outside a Texas department store. Roy Orbison first recorded the song in 1963, but Nelson released his own version the following year, creating a classic that belongs on any holiday playlist. 

 
11 of 22

"Roll Me Up and Smoke Me When I Die"

"Roll Me Up and Smoke Me When I Die"
Frederick Breedon/FilmMagic

A noted cannabis enthusiast, Nelson recorded “Roll Me Up and Smoke Me When I Die” at the ripe old age of 79 for his 2012 album, "Heroes." In addition to the iconic lyrics about Nelson’s plans for the afterlife, “Roll Me Up” also features killer piano playing from the aptly nicknamed Bobbie “Little Sister” Nelson, Nelson’s younger sister and essential member of his band.

 
12 of 22

"Whiskey River"

"Whiskey River"
Bettmann / Contributor

Perhaps the most recognizable song ever written about brown liquor, “Whiskey River” is an essential component of any Willie Nelson live performance. It's frequently found at the beginning of Nelson’s live set list and is all but guaranteed to get the party started. 

 
13 of 22

"Seven Spanish Angels"

"Seven Spanish Angels"
Hulton Archive/Getty Images

Nelson teamed up with legendary blues man Ray Charles for “Seven Spanish Angels,” released in 1984. A favorite of serious Nelson and Charles fans alike, the song tracks the story of an American outlaw and his lover, which ends tragically for both. 

 
14 of 22

"Good-Hearted Woman"

"Good-Hearted Woman"
Michael Putland/Getty Images

Co-written by Nelson and Waylon Jennings, “Good-Hearted Woman” was inspired by the tumultuous relationship of soul icon Tina Turner and her abusive husband, Ike. Jennings and Nelson recorded “Good-Hearted Woman” together in 1975 for "Wanted: The Outlaws!," which would become country music’s first platinum record after its release. 

 
15 of 22

"Always On My Mind"

"Always On My Mind"
Tom Hill/Getty Images

Johnny Christopher and Elvis Presley recorded “You Were Always On My Mind” before, but it wasn’t a massive, record-shattering hit until Nelson recorded this classic ballad in 1982. The title track of his seventh album, Nelson propelled the song to the top of the Billboard Hot Country and Adult Contemporary charts. Since then, it’s been inducted into the Grammy Hall of Fame and certified platinum. 

 
16 of 22

"Mammas Don't Let Your Babies Grow Up to be Cowboys"

"Mammas Don't Let Your Babies Grow Up to be Cowboys"
Richard E. Aaron/Redferns

“Mammas Don’t Let Your Babies Grow Up to be Cowboys” was first released in the 1950s by Ed Bruce, but it wasn’t a hit until Nelson’s iconic voice warbled its first verse. Later, alongside Waylon Jennings on the 1978 duet album, "Waylon & Willie," the song scored a Grammy Award in 1979 and an appearance in the Robert Redford-Jane Fonda film "The Electric Horseman." 

 
17 of 22

"Django & Jimmie"

"Django & Jimmie"
Gary Miller/Getty Images

Nelson teamed up with fellow Highwayman and lifelong friend Merle Haggard for Django & Jimmie, an album-length tribute to Django Reinhardt and Jimmie Rodgers, as both were instrumental in inspiring Haggard and Nelson to become the country music titans they eventually turned into. Released in 2015, it was the duo’s sixth and final collaboration together before Haggard’s death in 2016.

 
18 of 22

"Pancho and Lefty"

"Pancho and Lefty"
Beth Gwinn/Getty Images

Written by Texas songwriter Townes Van Zandt in the 1970s, Merle Haggard and Nelson made “Pancho and Lefty” a No. 1 hit in 1983. The title track of the country duo’s first album-length collaboration, the storyline of “Pancho and Lefty” follows two Mexican outlaws to the most dramatic of conclusions. 

 
19 of 22

"On The Road Again"

"On The Road Again"
Jay Dickman / Contributor

Nelson recorded this iconic ode to a musician’s life on the wide-open highway for the soundtrack of the 1980 film "Honeysuckle Rose," in which Nelson also stars. Legend has it that “On The Road Again” was penned on the back of a paper motion sickness bag, a humble beginning for a song that would later win Nelson a Grammy Award, an Oscar nomination and the hearts of millions of fans.

 
20 of 22

"Half A Man"

"Half A Man"
GAB Archives/Contributor

This arguably bizarre song, written about a man who literally only has half of a body, was written while Nelson was still a clean-shaven country crooner. Once you get past the oddity of the song’s premise, the deeper theme of losing part of oneself while losing a loved one makes total sense.

 
21 of 22

"Blue Eyes Crying In The Rain"

"Blue Eyes Crying In The Rain"
Paul Natkin/Getty Images

A cover of a Roy Acuff tune, Willie Nelson's version of "Blue Eyes Crying In The Rain" is totally unforgettable. It appears on Nelson's iconic 1975 album Red Headed Stranger, which was responsible for reviving the career of one of country's most iconic artists. 

 
22 of 22

"Highwayman"

"Highwayman"
Paul Natkin/Getty Images

Written by Jimmy Webb, "Highwayman" inspired the country supergroup Highwaymen, which brought together the incredible talents of Willie Nelson, Johnny Cash, Waylon Jennings, and Kris Kristofferson. Nelson leads off on the first verse, setting the tone for one of the most legendary outlaw country tracks in history. 

Amy McCarthy is a Texas-based journalist. Follow her on twitter at @aemccarthy

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