By the end of his witty and wistful new album, Tree of Forgiveness, John Prine has managed to squeak his way into Heaven, where he proceeds to play songs, smoke cigarettes, and forgive everyone who ever wronged him. It’s a happy ending, and it’s well-earned: Prine is nothing if not a survivor, and Tree of Forgiveness feels scrappy and hard-won, both in its sound and in its form. It’s been 13 years since the last set of original tunes from Prine, and this new collection is endearingly tattered and terse: Its 10 songs—with copyright dates that span decades—barely comprise half an hour of music, and something like “I Have Met My Love Today,” at under two minutes long, feels like a precious fragment, the dog-eared remnant of some holy text that Prine’s been carrying around in his wallet through periods of creative drought and bad health. Throat surgery and cancer both left their marks on his voice, never frailer and never more expressive than here, the perfectly weathered instrument for a songwriter who remains a bemused participant in life’s tender mercies and tragicomic indignities. His gristle brings the weight of wisdom to “The Lonesome Friends of Science,” a song for the discarded and the forgotten that hinges on the revoked planetary status of Pluto, which Prine knowingly says “never stood a chance no how,” and his droll detachment keeps the minor-key “Caravan of Fools” from congealing in its own despair; his off-handed disdain for the crimes of the plutocrats suggest that there’ve always been hard times, and so far we’ve always found a way to live through ‘em. Prine’s lyrics are hardscrabble and plainspoken, but never at the expense of local color; on “Knockin’ on Your Screen Door,” his rural vernacular is as commanding as Lucinda Williams’: “I was in high cotton, just a-bangin’ on my six-string/ A-kickin’ at the trash can, walkin’ skin and bone.” Meanwhile, the whole album bears a sympathetic Dave Cobb production, one that prizes simplicity but lights up with color when the songs call for it: “Knockin’ on Your Screen Door” is roughed-up, ramshackle blues, “When I Get to Heaven” is a whimsical jamboree, and “Summer’s End” is buoyed by understated, cinematic strings. Some of the songs sound like trifles at first, but the weightier songs give context to the slight ones, until you realize they’re not so slight at all: Prine is the pilgrim making progress, winding his way through sickness and death, the Caravan of Fools and the lonesome plight of Pluto, all the while aware that he’s in his twilight years. The key song here is “Summer’s End,” which grounds everything else in a certain eschatological urgency; “summer’s end came faster than we wanted,” Prine admits. It always does—but knowing how things end brings focus and perspective. “Boundless Love” takes on a hymn-like quality, and “God Only Knows” turns regret into something more like penitence and contrition. It’s as though he’s condensed all the ragged wisdom and experience of his lifetime into these hard-boiled tunes, and chiseled away anything superfluous. We’re left with the stuff that really matters: “Come on home,” Prine pleads on “Summer’s End.” “You don’t have to be alone.” Even on this side of heaven, boundless love is there for anyone seeking it.

Prine’s not the only grizzled pro who’s singing about matters of life and death. At 85, Willie Nelson has certainly earned the right to enter the sepia-toned phase of his career, and his new Last Man Standing is at least his third album in a row to confront mortality head-on: For the Good Times paid tribute to his late friend Ray Price, and God’s Problem Child found him tackling old age through a series of remembrances, autobiographical sketches, and sly jokes. Last Man Standing ups the joke content considerably, allowing Willie to confront his twilight years with a light touch, an amiable chuckle, and just a hint of sentimentality thrown in for good measure. The latter comes mostly in the form of “Something You Get Through,” a tender ballad about saying goodbye to someone you’ve loved a long time; the pain never subsides, Willie reckons, but maybe it makes you tougher. More characteristic of the album’s playful streak is “Bad Breath,” a surprisingly philosophical ode to halitosis: “Bad breath is better than no breath at all,” Willie sings. And then there’s the wistful second-guessing of the title track: “I don’t wanna be the last man standing/ Wait a minute, maybe I do.” To outlive your contemporaries is a lonesome achievement, but have you considered the alternative? Willie wrote all 11 of these songs with Buddy Cannon, who also produced the set—and if the red-headed stranger doesn’t mix his American music idioms with the same staggering virtuosity he showed in the days of Stardust and Shotgun Willie, he remains casually eclectic, seamless and smooth in his intermingling of folk forms. Last Man Standing is very much a roots record, one that’s equally charming when it offers burnished blues (“Bad Breath”), Texas swing (“Ready to Roar”), rollicking honky-tonk sing-alongs (“Don’t Tell Noah”), and smooth, folksy shuffles (“Me and You.”) For all its amiability, the record isn’t without some prickliness; John Prine may make it into Heaven, but Willie’s aware that “Hell is a-waitin’ there too.” Of course, he’s spent his career writing tough songs that sound smooth and easygoing; that’s the achievement of Last Man Standing, and it’s the achievement of his lifetime.

17^th Avenue Revival, new from the Oak Ridge Boys, has a couple of through-lines to the John Prine and Willie Nelson albums. Like Tree of Forgiveness, this nine-song collection was helmed by Dave Cobb, an in-demand country and roots producer whose reputation for traditionalism undersells his breadth and variety. This year alone, he shepherded the scrappy charm of Tree of Forgiveness, brought string-swept melodrama to Brandi Carlisle’s By the Way, I Forgive You, and helped Ashley Monroe revitalize emotive countrypolitanism on her sublime Sparrow. Here, he connects the Oak Ridge Boys to the spirit of the Million Dollar Quartet, bringing grit and immediacy to their southern gospel. 17^th Avenue Revival also fits with Tree of Forgiveness and Last Man Standing for how it finds grizzled veterans offering song of experience, ragged wisdom for summer’s end. “Brand New Star,” the opening song, forgoes Prine’s sly wit and Willie’s deadpan jokes in favor of pure sentimentality; the song reckons that a lost loved one has been turned into a celestial body, an idea that’s not found anywhere in the Bible but does fit with a certain cultural evangelicalism. The schmaltz is balanced out by a seemingly sincere read of Brandy Clark’s “Pray to Jesus”—a tune where desperation points to either religion or gambling, whichever saves you faster—and what’s more, it lands with visceral impact thanks to Cobb’s stripped-down production: It’s just the sound of four guys harmonizing in real time, keeping the beat through snapped fingers and the occasional hand clap, Cobb’s acoustic guitar the only instrumentation. There’s also the pummeling rockabiliy of “God’s Got It,” which sells its message of divine sovereignty through sheer barreling momentum, and an album-ending performance of “Let it Shine On Me” that builds to a sanctified hootenanny. The record is thick with the snap of the upright bass, the lingering dissonance of pounded pianos, and the rattle of tambourines—but on slower songs, like the hymn “I’d Rather Have Jesus,” the Oak Ridge Boys supply all their own special effects through those well-worn harmonies. Because he aligns these songs with the aesthetics of rock, country, and blues, Cobb rightly places Southern Gospel within the continuum of American folk traditions—and indeed, 17^th Avenue Revival sidesteps pageantry in favor of austere reflections on faith and devotion, its hopefulness in the Lord feeling tested and sincere. “Joy comes in the morning/ And outshines the darkest of nights,” one song says. They know as well as Prine does that summers end—but maybe that’s not the end of the story.