1936 – Born in Brownsville, Texas on the 22nd of June.
1960 – Kristofferson graduated with a master’s degree in English literature and married an old girlfriend, Fran Beer.
1960 – He was stationed in West Germany and returned to music and formed a band.
1965 – He resigned his commission to pursue songwriting. He had just been assigned to become an English Literature professor at West Point.
– Kristofferson moved to Nashville after resigning his commission, intent on becoming a professional songwriter.
1966 – Dave Dudley released a successful Kristofferson single, "Viet Nam Blues". The following year, Kristofferson signed to Epic Records and released a single, "Golden Idol"/"Killing Time", but the song was not successful.
1970 – His debut album for Monument was Kristofferson, which included a few new songs as well as many of his previous hits.
1971 – Janis Joplin, a very influential vocalist, had a #1 pop hit with "Me and Bobby McGee" from her posthumous Pearl.
1972 – He also swept the Grammies that year with numerous songs nominated and several winning song of the year. Kristofferson’s fourth album, Jesus Was a Capricorn initially had slow sales, but the third single, "Why Me", was a success and significantly increased album sales.
1973 – He appeared in Blume in Love and Pat Garrett and Billy the Kid and also married Rita Coolidge.
1982 – Kristofferson participated on The Winning Hand, a country success that failed to break into mainstream audiences.
1985 – Kristofferson starred in Trouble in Mind and released Repossessed, a politically aware album that was a country success, particularly "They Killed Him", a tribute to his heroes, including Martin Luther King, Jr., Jesus, and Mohandas Gandhi.
– Kristofferson was inducted into the Songwriters Hall of Fame and the Nashville Songwriters Hall of Fame in 1977.
1999 – Saw the release of The Austin Sessions.
2003 – Broken Freedom Song was released, a live album recorded in San Francisco.
2004 – He was inducted into the Country Music Hall of Fame.
2006 – He received the Johnny Mercer Award from the Songwriters Hall of Fame and released his first album full of new material in 11 years; This Old Road.
2007 – On the 21st of April, Kristofferson won CMT’s Johnny Cash Visionary Award. Rosanne Cash, Cash’s daughter, presented the honor during the April 16 awards show in Nashville.
– In July, Kristofferson was featured on CMT’s "Studio 330 Sessions" where he played many of his hits.