Kris Kristofferson, who was 88 when he died Saturday, embedded enduring aphorisms into his songs. “Freedom’s just another word for nothing left to lose,” he observed in “Me and Bobby McGee.” In “Help Me Make It Through the Night,” he wrote, “Yesterday is dead and gone/And tomorrow’s out of sight.” And in “For the Good Times,” he urged, “There is no need to watch the bridges that we’re burning.”

Those are stoic lines, delivered matter-of-factly, often tucked into tales about facing up to some kind of loss: of a lover, a friend, a hope, a chance, fleeting time. Kristofferson’s characters are often isolated, luckless, drunk or high, but they’re still seeking redemption or at least trying to move on — like Casey, in “Casey’s Last Ride,” who was “seeing his reflection in the lives of all the lonely men/who reach for anything they can to keep from going home.”

Kristofferson established himself as a songwriter as the 1970s began, and his early songs were his most lasting ones. His willingness to sing unpretty stories and his homey melodies were foundations for the outlaw country movement of the 1970s. Bob Dylan has said, “You can look at Nashville pre-Kris and post-Kris, because he changed everything.”

After a detour through 1970s movie stardom, Kristofferson shared the outlaw movement’s victory lap, in the 1980s, when he joined Johnny Cash, Willie Nelson and Waylon Jennings in the Highwaymen. He went on to write politically charged songs and the homilies of an elder. His voice was serviceable but not striking in his early years, and it grew much gruffer through the decades. But it was always forthright enough to put across the unvarnished substance of his music.

Here, in chronological order, are 12 of Kristofferson’s essential songs.

“Me and Bobby McGee” (1970): Kristofferson’s own version of this tale of hitchhiking, harmonica-playing lovers, from his debut album, is far more wistful and less cathartic than Janis Joplin’s No. 1 hit version, released in 1971 after her death. Where she turned its outro of “la-da-das” into an ecstatic rave-up, Kristofferson lets them trail off, like a memory receding into the distance.

“Help Me Make It Through the Night” (1970): A potential hookup becomes a prayerful moment in “Help Me Make It Through the Night,” as Kristofferson urges, “Let the devil take tomorrow/Lord, tonight I need a friend.” It’s a plea for comfort that’s also one of Kristofferson’s most elegant melodies, with every symmetrical phrase leading, step by step, to the title refrain.

“For the Good Times” (1970): “Make believe you love me one more time,” the singer urges in this entreaty for a farewell tryst. It’s a classic ballad, so neatly constructed that both the country singer Ray Price and the soul singer Al Green could make it their own.

“Sunday Mornin’ Comin’ Down” (1970): Hung over after a Saturday night gig, Kristofferson’s narrator stumbles out on Sunday morning. He sees children playing and smells chicken frying for some family’s dinner. “It took me back to somethin’/that I’d lost somehow, somewhere along the way,” he sings; a church bell rings behind him. The band sounds like gospel, but he’s not ready to be uplifted.

“The Silver Tongued Devil and I” (1971): In a near-parable disguised as a barroom waltz, with some tinkling honky-tonk piano, the singer watches a “tender young maiden” get seduced by a devil, who’s “hiding intentions of evil under the smile of a saint.” There’s some of himself in his rival — “some people swear he’s my double/and some even say we’re the same” — but the singer is only mortal, and the girl has made her choice.

“The Pilgrim, Chapter 33” (1971): Kristofferson mythologizes the figure of a down-and-out itinerant songwriter in a Johnny Cash-style march. “He’s a poet and he’s a picker”; he’s also “a walking contradiction, partly truth and partly fiction.” In the intro he names some real-life examples, including Cash; he doesn’t include himself.

“Border Lord” (1972): In this lean, bluesy song, Kristofferson sketches a fugitive life of “leavin’ every yesterday behind” and “runnin’ like you’re runnin’ out of time,” but “takin’ any comfort you can find” while it lasts. He liked the idea enough to name his 1980s band the Borderlords.

“Nobody Wins” (1972): As terse, precise and old-fashioned as a song from Ernest Tubb or Hank Williams, “Nobody Wins” perfectly dissects and settles a romantic dead end. “It’s a shame to make the same mistakes again and again/It’s over — nobody wins.” Every syllable hits home.

“Shandy (The Perfect Disguise)” (1974): The tone is jovial, with Kristofferson’s voice answered by a twangy sitar and singalong harmonies rising behind him. But the narrative is enigmatic and twisted, involving drugs and a dangerous liaison, culminating in a paradoxical chorus: “Lies ain’t no harder than tellin’ the truth/truth is the perfect disguise.”

“What About Me” (1986): Kristofferson grapples with the toll of war in a track with the Borderlands about a soldier and a wartime survivor. The song is topical with religious undertones. The soldier is an addict, while the survivor, orphaned after her parents were killed, is from El Salvador, the country name that translates as “The Savior.” Later the narrator meets “the Warrior Jesus Christ” and goes on to mention the Sandinistas in Nicaragua, another revolution in progress.

“Closer to the Bone” (2009): “Ain’t you getting better/Running out of time,” a gruff-voiced Kristofferson sings. “Everything is sweeter closer to the bone.” With a grizzled voice over an acoustic band with drums, he makes aging sound worth its ravages.

“Feeling Mortal” (2013): Kristofferson released his final studio album a decade ago. His voice was gravelly, but his mind was sharp. “Feeling Mortal,” the album’s title track, uses only acoustic and electric guitars. “I’ve begun to soon descend like the sun into the sea,” he sang. “And I thank my lucky stars I’m here into eternity.” It’s humble. But it’s also rightfully proud.