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Heralded as an artist’s artist, the three-time GRAMMY winner has recorded 27 albums, including three with pals Willie Nelson, Johnny Cash and Waylon Jennings as part of the Highwaymen. Kristofferson has spent three decades performing concerts all over the world, in most recent years in a solo acoustic setting, which puts the focus on the songs. “There’s an honesty in the sparseness. It feels like direct communication to the listener,” he says. “I still have more fun when I’m with the band, but being alone is freer, somehow. It’s like being an old blues guy, just completely stripped away.”
Kristofferson achieved remarkable success as a country songwriter at the start of the 1970s. His songs “Me and Bobby McGee,” “Help Me Make It Through the Night,” “Sunday Morning Coming Down,” and “For the Good Times,” all chart-topping hits, helped redefine country songwriting. By 1987, it was estimated that more than 450 artists had recorded Kristofferson’s compositions.