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Country - Released January 1, 1971 | SMSP

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By the time Monument came to release Kristofferson's second album, The Silver Tongued Devil and I, in July 1971, he was the author of four songs that had topped the country or pop charts for others. Kristofferson himself had not yet reached the charts with a recording of his own, but his spectacular success as a songwriter made The Silver Tongued Devil and I a much-anticipated record. One consequence of this was that Monument was willing to spend more money; three of the album's songs boasted strings and another a horn section. But the key, of course, was still the songwriting, and though there were several excellent songs, the album could not live up to its predecessor, which was the culmination of years of writing. Typically for a second album, Kristofferson reached back into his catalog, presenting his own treatments of "Jody and the Kid" and "The Taker," which had been hits for Roy Drusky and Waylon Jennings, respectively. In his newly written material, Kristofferson continued to examine the lives of society's outcasts, but the antiestablishment tone of some of Kristofferson was gone along with much of the wry humor, and in their place were touches of morbidity and sentimentality. Kristofferson retained his gift for intimate love songs, and the album's most memorable selections turned out to be "Loving Her Was Easier (Than Anything I'll Ever Do Again)" (which became a semi-standard) and "When I Loved Her." And even if his observations seemed less acute, his talent for wordplay often rescued the songs from banality. On its way to becoming a gold record, The Silver Tongued Devil and I reached the pop Top 20, Kristofferson's career high on that chart, and the country Top Five; thus, Kristofferson made the transition from being a successful songwriter to a successful recording artist. © William Ruhlmann /TiVo
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Country - Released January 1, 1970 | Legacy Recordings

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Country - Released February 15, 2004 | Columbia - Legacy

The two-CD Essential Kris Kristofferson compilation isn't a balanced retrospective of his lengthy career, heavily emphasizing his 1969-1971 recordings, which in fact comprise all of disc one. And it doesn't represent many of his albums at all (particularly the ones not done for Monument or Columbia), including just one post-1985 track. On the other hand, for the vast majority of Kristofferson listeners who want a best-of that offers more than a single-disc greatest-hits anthology can, it serves its purpose well. His best-known songs are here, in the original Kristofferson-sung versions: "Me and Bobby McGee," "Help Me Make It Through the Night," "Sunday Mornin' Comin' Down," "Why Me," and "For the Good Times." His earliest Monument records are sampled particularly deeply, with no less than nine of the 12 songs from his 1970 debut, Kristofferson, appearing. Still, there's no doubt that his early work was his most popular and best, and the disproportionate representation allows for the appearance of good songs from the era that escape skimpier greatest-hits collections. And there's no doubt that disc two, devoted almost entirely to post-1971 material, is less impressive and consistent, not to mention more haphazardly organized in its chronology, with the 1972 track "Why Me" appearing as the second-to-last cut. Room's also made for a few songs Kristofferson recorded with others, those being "I'd Rather Be Sorry" (a duet with Rita Coolidge), "Highwayman" (done with Waylon Jennings, Willie Nelson, and Johnny Cash), and "How Do You Feel About Foolin' Around" (on which he paired with Willie Nelson). © Richie Unterberger /TiVo
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Country - Released February 10, 2017 | Rhino Atlantic

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Country - Released January 1, 1971 | Legacy Recordings

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By the time Monument came to release Kristofferson's second album, The Silver Tongued Devil and I, in July 1971, he was the author of four songs that had topped the country or pop charts for others. Kristofferson himself had not yet reached the charts with a recording of his own, but his spectacular success as a songwriter made The Silver Tongued Devil and I a much-anticipated record. One consequence of this was that Monument was willing to spend more money; three of the album's songs boasted strings and another a horn section. But the key, of course, was still the songwriting, and though there were several excellent songs, the album could not live up to its predecessor, which was the culmination of years of writing. Typically for a second album, Kristofferson reached back into his catalog, presenting his own treatments of "Jody and the Kid" and "The Taker," which had been hits for Roy Drusky and Waylon Jennings, respectively. In his newly written material, Kristofferson continued to examine the lives of society's outcasts, but the antiestablishment tone of some of Kristofferson was gone along with much of the wry humor, and in their place were touches of morbidity and sentimentality. Kristofferson retained his gift for intimate love songs, and the album's most memorable selections turned out to be "Loving Her Was Easier (Than Anything I'll Ever Do Again)" (which became a semi-standard) and "When I Loved Her." And even if his observations seemed less acute, his talent for wordplay often rescued the songs from banality. On its way to becoming a gold record, The Silver Tongued Devil and I reached the pop Top 20, Kristofferson's career high on that chart, and the country Top Five; thus, Kristofferson made the transition from being a successful songwriter to a successful recording artist. © William Ruhlmann /TiVo
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Country - Released September 1, 1973 | A&M

Kris Kristofferson was at his commercial peak as a recording artist at the time that Full Moon, his first duo album with Rita Coolidge, was released in September 1973. His single "Why Me" had topped the country charts two months earlier, and his album Jesus Was a Capricorn was about to do the same thing. And, only weeks before Full Moon's release, the couple had gotten married. All of that made for a terrific send-off for the record, which benefited the careers of both participants. Not surprisingly, it was an album of love songs. Despite Kristofferson's greater celebrity, the LP was made with Coolidge's strengths in mind. David Anderle, its producer, was her producer, and it was released on her record label, A&M. The songs were set in her key, with Kristofferson crooning along in an unusually high register. The tempos were mostly slow, emphasizing the dreamy quality of Coolidge's voice. And the songs were mostly covers, though there were two joint compositions by the couple, one old Kristofferson song ("From the Bottle to the Bottom," a Top 20 country hit for Billy Walker in 1969), and one new Kristofferson tune, the Caribbean-flavored "A Song I'd Like to Sing," which was released as the first single and became a Top 40 pop hit while also reaching the country and easy listening charts. With that, the album became a number one country hit. "From the Bottle to the Bottom" won the 1973 Grammy Award for Best Country Vocal Performance by a Duo or Group. The album's second single, a cover of Tom Jans' "Loving Arms," also made the pop, country, and easy listening charts, and because it was released in the 1974 eligibility period for the Grammy Awards, it earned the couple a second nomination in the same category the following year. © William Ruhlmann /TiVo
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Country - Released June 10, 2016 | Legacy Recordings

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Country - Released August 7, 2007 | Monument - Legacy

If you're looking for the basics from singer/songwriter Kris Kristofferson's early-'70s Monument catalog, 16 Biggest Hits fits the bill. Kristofferson's coarse vocals considerably change the dynamic of songs like "Me and Bobby McGee," "Sunday Mornin' Comin' Down," "Once More with Feeling," "For the Good Times" and "Help Me Make It Through the Night," from those of the artists' who actually took the songs to the top of the rock and country charts. Also of note is Kristofferson's "Why Me," his first chart entry as vocalist in 1972, and the 1984 hit "Highwayman," recorded by the short-lived supergroup of the same name featuring Waylon Jennings, Willie Nelson and Johnny Cash. While this compilation is highly recommended, for those listeners who want to go deeper into his catalog, pick up The Essential Kris Kristofferson on Columbia/Legacy, as it includes choice album cuts and duets with Willie Nelson and Rita Coolidge. © Al Campbell /TiVo
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Country - Released November 1, 1982 | Monument - Legacy

Recorded for Monument in 1983 thanks to the leniency of the artists' respective labels, Brenda, Dolly, Kris & Willie brought together Brenda Lee, Dolly Parton, Kris Kristofferson and Willie Nelson for a double album of duets featuring every possible combination of the four, as well as a handful of solo numbers. Certainly a delight for fans of the individual performers, this album is nonetheless too redolent of a various-artists anthology to truly succeed as a piece. Much of the music is highly enjoyable, however, particularly the Dolly and Kris novelty, "Ping Pong," and Brenda and Dolly's duet on What Do You Think About Lovin'." As a bizarre bonus, Johnny Cash provided the half-poetry, half-prose liner notes. © Greg Adams /TiVo
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Country - Released November 1, 1972 | Legacy Recordings

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Country - Released January 1, 1970 | Monument - Legacy

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Country - Released January 1, 1973 | A&M

Kris Kristofferson was at his commercial peak as a recording artist at the time that Full Moon, his first duo album with Rita Coolidge, was released in September 1973. His single "Why Me" had topped the country charts two months earlier, and his album Jesus Was a Capricorn was about to do the same thing. And, only weeks before Full Moon's release, the couple had gotten married. All of that made for a terrific send-off for the record, which benefited the careers of both participants. Not surprisingly, it was an album of love songs. Despite Kristofferson's greater celebrity, the LP was made with Coolidge's strengths in mind. David Anderle, its producer, was her producer, and it was released on her record label, A&M. The songs were set in her key, with Kristofferson crooning along in an unusually high register. The tempos were mostly slow, emphasizing the dreamy quality of Coolidge's voice. And the songs were mostly covers, though there were two joint compositions by the couple, one old Kristofferson song ("From the Bottle to the Bottom," a Top 20 country hit for Billy Walker in 1969), and one new Kristofferson tune, the Caribbean-flavored "A Song I'd Like to Sing," which was released as the first single and became a Top 40 pop hit while also reaching the country and easy listening charts. With that, the album became a number one country hit. "From the Bottle to the Bottom" won the 1973 Grammy Award for Best Country Vocal Performance by a Duo or Group. The album's second single, a cover of Tom Jans' "Loving Arms," also made the pop, country, and easy listening charts, and because it was released in the 1974 eligibility period for the Grammy Awards, it earned the couple a second nomination in the same category the following year. © William Ruhlmann /TiVo
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Country - Released June 10, 2016 | Legacy Recordings

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Country - Released June 9, 1992 | Legacy Recordings

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Country - Released October 1, 1986 | Mercury Nashville

After Kris Kristofferson's ninth and tenth solo albums, Shake Hands With the Devil (1979) and To the Bone (1980), missed the charts, he did not make another album on his own for more than six years, in the meantime contributing to three albums recorded with others: Kris, Willie, Dolly & Brenda ... The Winning Hand (1982) (with Willie Nelson, Dolly Parton, and Brenda Lee); the soundtrack Music From Songwriter (1984) (with Nelson), which contained four Kristofferson solo tracks; and Highwayman (with Nelson, Johnny Cash, and Waylon Jennings). The last was a major success, topping the country charts, and probably interested Mercury Records in giving Kristofferson a new contract as a solo artist. The result was his 11th solo album, Repossessed, its title containing a telling double meaning. Kristofferson billed his backup group, the Borderlords, on the cover, a reasonable decision since they included such notable figures as Donnie Fritts and Billy Swan, who occasionally stepped in to sing a verse of a song here and there in place of the leader. Also, the tracks had a true country-rock band feel, and Kristofferson sometimes introduced the songs or called out solos as if they were playing a set in a club. The tracks thus had a kinetic feel, and that was all to the good since the songs themselves were not very impressive. 1986-1987 was a period of political unrest, as left-wing activists feared another Vietnam in El Salvador, and Kristofferson explored that concern in "What About Me," while such songs as "Shipwrecked in the Eighties," "They Killed Him," and "Anthem '84" reflected on various aspects of politics and war. But there were no real insights to be found in the songwriter's sketchy and abstract descriptions, either in these songs or the more philosophical statements such as "The Heart" (chorus: "The heart is all that matters in the end") and "Love Is the Way." In a lull in his film career, Kristofferson promoted Repossessed with extensive touring and managed to keep it in the country album charts six months, with "They Killed Him" (which Bob Dylan had thought enough of to cover) getting into the lower reaches of the singles charts. But it was not one of his better records. © William Ruhlmann /TiVo
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Country - Released August 8, 1972 | Legacy Recordings

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Country - Released December 1, 1974 | Legacy Recordings

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Country - Released November 1, 1975 | Legacy Recordings

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Country - Released November 1, 1972 | Legacy Recordings

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Country - Released November 17, 1974 | Legacy Recordings

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Kris Kristofferson in the magazine
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