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01
He was set to become a Major when he decided to quit the United States Army Rangers after almost five years.
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02
He is a former United States Army Rangers captain who graduated Airborne School, Ranger School, and flight school, served in Germany, and volunteered for Vietnam as a helicopter pilot. Instead he was offered a professor of English Literature position at USMA West Point. Disappointed, he resigned in 1965.
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03
His start in music came from landing a helicopter in Johnny Cash’s backyard and presenting him with a song. Cash went on to record that song.
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04
He was good friends with Muhammad Ali and Willie Nelson, and very close with the late Johnny Cash.
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05
When Kristofferson hosted the season finale of Saturday Night Live in 1976, the cast and crew reported he was drunk but still managed to pull off the show. He later said drinking helped his stage shyness.
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06
He was a member of The Highwaymen along with Johnny Cash, Waylon Jennings, and Willie Nelson.
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07
In 2013 he admitted suffering from short-term memory loss for several years. He was initially misdiagnosed with Alzheimer’s disease but that later proved incorrect.
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08
He was inducted into the Country Music Hall of Fame in 2004.
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09
He first grew a beard during a hospital stay and kept it because it made him look older.
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10
He got the leading male role in A Star Is Born 1976 after Elvis Presley could not do it. Elvis also recorded a song written by Kristofferson.
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11
A fitness fanatic most of his life, he worked out rigorously until the mid-1990s, running seven miles daily, using a punching bag, rowing machine, and swimming.
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12
He was friends with Jeff Bridges and fellow Texan Tommy Lee Jones, as well as the late Warren Oates.
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13
His brother Kraigher Kristofferson is also a veteran, serving as a U.S. Navy fighter pilot in the Vietnam War.
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14
He was inducted into the Texas Film Hall of Fame on March 10, 2006, along with Matthew McConaughey, JoBeth Williams, Cybill Shepherd, and Lyle Lovett.
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15
He wrote Me and Bobby McGee, which Janis Joplin recorded. Roger Miller had a hit with it in 1969 before Kristofferson even finished writing it.
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16
Sam Peckinpah cast him as Billy the Kid in Pat Garrett & Billy the Kid 1973 after seeing him perform at The Troubadour and in Cisco Pike 1971.
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17
A couple of years after leaving the army, Kristofferson joined the Tennessee National Guard and flew helicopters.
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18
The Rhodes Scholarship he won to study at Oxford is considered the world’s most prestigious academic scholarship. Other notable Rhodes scholars include Bill Clinton, Dean Rusk, Edwin Hubble, Terrence Malick, and Naomi Wolf.
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19
He played football with Burt Reynolds in preparation for Semi-Tough 1977; both were outstanding college players, with Reynolds nearly turning pro.
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20
Father of Tracy Kristofferson b. 1962 and Kris Kristofferson b. 1968 with Frances Beir; daughter Casey Kristofferson b. 1974 with Rita Coolidge; and Jesse Turner Kristofferson b. 1984, Jody Ray Kristofferson b. 1985, Johnny Kristofferson b. 1988, Kelly Marie Kristofferson b. 1991, and Blake Cameron Kristofferson b. 1994 with Lisa Marie Meyers.
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21
He used to work as a commercial helicopter pilot.
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22
He became good friends with the late James Coburn after working together on Pat Garrett & Billy the Kid 1973, Convoy 1978, and Payback 1999. Coburn also sang backup on Kristofferson’s album Who’s to Bless and Who’s to Blame.
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23
In 1970, he won the Country Music Song of the Year Award for Sunday Morning Coming Down as well as the Country Music Songwriter of the Year Award.
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24
It is speculated that Kristofferson, Warren Beatty, Cat Stevens, or Mick Jagger inspired Carly Simon’s You’re So Vain. Kristofferson dismissed it, saying he never flew a Lear jet like the guy in the song.
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25
He was a skilled boxer, rugby, and football player until a string of serious injuries forced him to quit.
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26
He attended Pomona College in Claremont, California, earning a B.A. in Creative Literature in 1958.
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27
He is one of the Four Horsemen of the Country Music Apocalypse along with Johnny Cash, Waylon Jennings, and Willie Nelson.
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28
In June 1999, he underwent elective heart bypass surgery.
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29
He was among those considered for the role of John Rambo in First Blood 1982; some producers hoped it would interest his friend Sam Peckinpah.
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30
He was set to star in Hanover Street 1979 but dropped out for a concert tour; Harrison Ford got the part.
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31
He is friends with Jackson Browne and they toured together. Kristofferson mentions Browne in his song Eddie the Eunuch.
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32
One of the few male celebrities to appear as a model in both Playgirl and Playboy. The Playboy shoot with Sarah Miles was done while drunk; he regretted it and could not remember doing it.
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33
He and wife Rita Coolidge appeared on The Muppet Show 1976 as one of three married couples to do so, alongside Roy Rogers and Dale Evans and Robert Shields and Lorene Yarnell.
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34
A young Kris Kristofferson is visible on one of his album covers in Martin Scorsese’s Taxi Driver 1976.
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35
He did not talk to his mother for 25 years.
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36
He never had an acting lesson.
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37
He was asked to try out for the U.S. Special Forces but declined.
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38
He was inducted into the Songwriters Hall of Fame in 1985.
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39
He wrote two tribute songs to Sam Peckinpah: Sam’s Song Ask Any Working Girl and One for the Money.
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40
An avid golfer.
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41
He turned down a teaching position at West Point to pursue songwriting in Nashville.
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42
Close friend of Joan Baez.
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43
He tested for the part of Superman in Superman 1978.
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44
His favorite actors were William Holden, Robert Ryan, and Gregory Peck.
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45
Cameron Crowe posed as a student at Clairemont High School for Fast Times at Ridgemont High 1982; the principal agreed after learning Crowe knew Kristofferson.
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46
As a kid, his heroes were Hank Williams and Rocky Graziano.
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47
Among his personal heroes were Martin Luther King Jr., Jesus Christ, and Mohandas Gandhi.
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48
He earned a Ph.D. in literature at Oxford, working construction jobs to support himself.
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49
The American Veteran Awards named him Veteran of the Year in 2002.
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50
He was the first choice for the role of The Driver in Two-Lane Blacktop 1971.