At 14 words, All the Things That I Did and All the Things That I Didn’t Do is an album title calling out for a shorthand. Consider a helpful phrase from the accompanying press release, “waltzing into disaster,” which captures well the album’s spirit of whimsy and foreboding. Its dozen songs, clear-eyed and bruised, reflect an older, more weathered version of The Milk Carton Kids, hobbling forward in the wake of disasters both personal and cultural. It’s an album whose margins are haunted by remembrances of runaway lovers and a nation that’s all but vanished; its narrators still remember how thing used to be, and sigh in the opening lines: “Just look at us now.” And, it’s an album that dreams a highway through the backwoods and byways of American folk song, employing canonical forms for their emotional directness and uncluttered sense of narrative. These are—to borrow another recently-popular title—songs of experience, tattered but true.

The Milk Carton Kids are Joey Ryan and Kenneth Pattengale, both of whom play acoustic guitar, sing in close, single-mic harmonies, and dodge comparisons to Simon & Garfunkel (and also Gillian Welch and Dave Rawlings) that have never felt quite right; as songwriters, Ryan and Pattengale are engaged with an older school of parlor songs and soft-shoe routines that convey deep melancholy through wistful, romantic melodies. These new songs of experience, all of them originals, are their best work to date, conveying the emotional acuity and formal control of the great American songbook. They are plainspoken, and they contain multitudes. “Mourning in America,” a state of the union in the Rhymin’ Simon vein, reflects political dislocation through street-level detail and a sense of mundane weariness; “You Break My Heart” is a song about every heartbreak, even though it was pretty clearly written about a particular one.

This is the first Milk Carton Kids album to be recorded with outside musicians, and to guide them through this new adventure Ryan and Pattengale enlisted Joe Henry, a producer who’s developed a strong catalog of albums that wring spontaneity and joyful abandon from hallowed folk forms (for examples, see his work with Allen Toussaint, Aaron Neville, or his own recent Thrum). Henry presided over Nashville sessions that brought in a rich cast of supporting players. Levon Henry’s clarinet snakes through the fleet-footed “Younger Years,” while Russ Pahl’s pedal steel sounds like a high-and-lonesome train whistle in the background. Brittany Haas’ fiddle leads off “Big Time,” something like a last waltz crossed with a barn-burning hootenanny. Spectral, lovelorn ballads like “I’ve Been Loving You” have their edges frayed by ghostly piano and steel guitar, while “Blindness,” a haunted house of a song, seems to be dissolving as it plays, an apparition fading back into shadow. There are subtly cinematic effects in every song here, and none as good as the harmonies of the Milk Carton Kids themselves; the genius of this record is how it broadens their scope while maintaining the centrality of their chemistry. It never doesn’t sound like a Milk Carton Kids album.

The result is an album that takes cues from some of the ramshackle myth-making of The Basement Tapes; the well-worn, second-hand Americana of Gram Parsons; the casual virtuosity with which Willie Nelson synthesizes roadhouse roots into something seamless and supple, with Pattengale’s ragged lead guitar ably filling in for Trigger. The album’s centerpiece is “One More for the Road,” an impressionistic epic that stretches Sinatra’s wee-small-hours desolation across the broader canvas of the American frontier, a saloon song by way of a campfire rag.  “Nothing is Real” is weary juke joint R&B, swaying in place to its dawning disillusionment. “Younger Years” recalls the wispy cowboy songs of Marty Robbins, while “You Break My Heart” is a lovelorn standard, thread-bear ruminations from a spectral Cole Porter. “I’ve Been Loving You” marries songbook formalism to country twang so ably, it sounds as though it should have been included on Stardust.

The songs were born of fracture and chaos—break-ups and relocations, health scares and a declining national mood. They sound suitably beleaguered and wary in their evocations of wayward countries and faithless lovers, and it is occasionally hard to tell whether a given line is meant to reflect personal crisis or the broader tragedies unfolding around us. (For that particular synthesis, there remains no better model than Joe Henry’s 2007 album Civilians, a singular songwriting achievement of such elegant and alluring metaphors, it can’t help but be seminal for younger writers like Ryan and Pattengale.) “Just Look at Us Now,” chronicles the curdling of youthful idealism: “We wanted to prove we were something, we were special/ We knew in our hearts we weren’t the only ones,” the song goes, and it could just as easily be a story of fated lovers or of an exceptional empire’s slow crumble. “Make me another promise if you dare,” Ryan sings, hard-won skepticism from someone who’s been through the ringer. “Mourning in America” allows for less ambivalence, capturing a disheartened trudge through an atmosphere of malaise. Later, when Ryan and Pattengale sing “I’ve been loving you all wrong,” it could be either the patriot’s boondoggle or the fool’s sad revelation; either way, they sing it like it’s too little, too late. “Unwinnable War” imagines love as a battlefield, though there’s always the outside chance it’s just about the battlefield as a battlefield; even “Big Time,” ostensibly a party jam, masks a menacing eschatology: “This’ll be the last time/ we’re gonna have a big time.”

These are all familiar lessons from the Songbook, learned anew with each new generation: The times, they change. Things fall apart. We come, in the age’s most uncertain hour, singing American tunes. The Milk Carton Kids end their album with a great one. “All the Things…,” performed by Pattengale with haunting vulnerability, is a divorce song, written from a place of reflection and regret. But for its bridge, the spare arrangement suddenly breaks open into a full-color dream sequence, Ryan joining in and the two of them daring to imagine something like peace and reconciliation. They sound like they know they’re not the first to wake up and find their house in shambles; to lift up a song for better days.