In the spring of 1977, Kris Kristofferson was at the apex of his film career, having recently co-starred in the box-office hit A Star Is Born and won a Golden Globe Award for it. At the same time, his recording career was on the wane; his two most recent solo albums, Who's to Bless...and Who's to Blame (1975) and Surreal Thing (1976) had failed to break into the top 100 of the pop LP charts. Monument Records seized on his movie celebrity to release his first compilation, which emphasized his early success as a songwriter over his actual recordings. In 1970-71, he had scored four number one hits as a writer -- "Help Me Make It Through the Night," "For the Good Times," and "Sunday Mornin' Comin' Down" on the country charts, and "Me and Bobby McGee" on the pop charts. All four songs had appeared on his debut album, Kristofferson (aka Me and Bobby McGee), and they were featured on the first side of Songs of Kristofferson along with the title track of his second album, The Silver Tongued Devil and I (1971), and his first Top 40 pop hit as a performer, "Loving Her Was Easier (Than Anything I'll Ever Do Again)," also from his second album. The second side of the LP plucked another song, "The Pilgrim: Chapter 33," from the second album, along with two tracks each from Who's to Bless...and Who's to Blame and Surreal Thing, plus "Why Me," Kristofferson's 1973 country chart-topper and top 20 pop hit. The compilers left out such minor chart entries as "Josie" and "Jesus Was a Capricorn," giving undue weight to the later, less successful work, which keeps Songs of Kristofferson from being a true best-of. But it does contain the highlights of his early recordings, which remained his best-known material over time, and fans responded favorably to having the material on one album, as the LP went gold within two years of release.
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AllMusic Review by William Ruhlmann