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01
After giving up his seat on the fatal 1959 flight, Jennings jokingly told Buddy Holly he hoped his plane crashed, but he was remorseful and felt responsible for years.
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02
Jennings was originally scheduled to be on the 1959 flight that killed Buddy Holly, Ritchie Valens, and the Big Bopper, but he surrendered his seat to the Big Bopper who was ill and preferred flying to riding the bus.
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03
Refusing to attend awards shows on principle, Jennings won two Grammy Awards and four CMA Awards, and he skipped his own induction into the Country Music Hall of Fame in 2001.
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04
His son Shooter Jennings portrayed him in the 2005 film Walk the Line.
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05
In December 2001, his left foot was amputated due to complications from diabetes.
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06
Jennings overcame a 20-year cocaine addiction in 1984; at its peak, he spent $1,500 daily on cocaine.
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07
In the mid-1980s, Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson formed the supergroup The Highwaymen, releasing albums and touring.
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08
Stevie Nicks wrote Leather & Lace in 1981 at Jennings’s request, intending for him and his wife Jessi Colter to record it, but by the time Nicks finished the song, the couple had separated; Nicks recorded it with Don Henley instead, and it reached #6 on the US charts.
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09
Early in his career, Jennings played bass in Buddy Holly’s band.
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10
Worldwide, Jennings sold over 40 million albums and singles and scored 16 #1 country hits.
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11
His son Shooter Jennings, born in 1979, sang with the Los Angeles band Stargunn.
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12
Jennings named his former residence in Brentwood, Tennessee, Southern Comfort.
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13
He smoked six packs of cigarettes daily until triple heart bypass surgery in December 1988.
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14
In 1984, Jennings stated he wished to be remembered for his music, not for his image.
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15
He was named Male Vocalist of the Year by the Country Music Association in 1975.
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16
After doctors advised him to stop touring, Jennings auctioned off much of his equipment, but he resumed performing less than a year later.
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17
Jennings said guitarist Jimmy Byrd was the only other person who could play his trademark chicken picking style and often called him Abe Lincoln because of his resemblance to Abraham Lincoln.
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18
Though he dropped out of high school, Jennings earned his GED in 1989.
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19
He was considered the central force of The Highwaymen, having brought together Johnny Cash, Willie Nelson, and Kris Kristofferson, all friends from the 1960s.
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20
Jennings appeared in TV movies such as Stagecoach 1986, The Oklahoma City Dolls 1981, Follow That Bird 1985, and the musical Nashville Rebel 1966.
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21
His other hit singles include I’m a Ramblin’ Man, Amanda, Lucille, I’ve Always Been Crazy, and Rose in Paradise.
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22
He is survived by his fourth wife Jessi Colter and seven children.
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23
Jennings was inducted into the Nashville Songwriters Hall of Fame in 1995 and the Country Music Hall of Fame in 2001.
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24
Jennings was married and divorced three times before his fourth marriage to Jessi Colter.
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25
He worked as a disc jockey at a Lubbock, Texas radio station.
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26
Jennings narrated the trailer for the 1975 film Moonrunners and also appeared in it as the storyteller.
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27
He is considered one of the Four Horsemen of the Country Music Apocalypse alongside Willie Nelson, Kris Kristofferson, and Johnny Cash.
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28
Jennings’s Greatest Hits album, released in 1979, sold four million copies, a rare feat in country music at the time.
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29
He began smoking at age ten.
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30
Jennings won a Grammy Award for his version of MacArthur Park recorded with The Kimberleys.
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31
He underwent surgery on both hands in June 1994 for carpal tunnel syndrome.
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32
Jennings was diagnosed with diabetes in 1981.