John Prine's catalog only gets better with age. Now in his early 70s, the artist, from suburban Chicago, has amassed a body of work on par with any of America's folk greats. Occasionally topical, sometimes humorous, and almost always thought-provoking, his songs often cut straight to the heart of existential dread – mixing tragedy and cynicism with the everyday realities of often-marginalized characters. As a result, they feel timeless, seeing as they usually emphasize people and personalities. This week, Prine releases The Tree of Forgiveness, his first album of completely original tunes since 2005. (Spoiler alert: it's terrific). Before we spend our weekend giving it plenty of spins, let's look at five of Prine's many standout moments.

"Angel from Montgomery"
A 1971 song that appears on Prine's self-titled debut, this wise-beyond-its-years tale of fading dreams immediately established the singer as a striking documenter of American life. "I am an old woman named after my mother," Prine sings to open the tune, the simple line conveying the passage of time as well as waning youth. Then, in under four minutes, Prine sketches a vivid picture of her life – flies buzzing in the kitchen, the nostalgia for a younger, wilder lover – and delivers the lyrics with the journalistic-like detachment of Bob Dylan. The guitars feel sympathetic, and an organ brings a bit of fire but can never seem to work up a consistent energy. It all builds to a crushing line: "How the hell can a person go to work in the morning/And come home in the evening and have nothing to say?" As a young man in his mid-20s, Prine penned a dirge, written about someone whose life should only be half finished.

"Far from Me"
Another cut from Prine's absolutely essential debut, "Far from Me" also deals with dashed expectations but puts the spotlight on far-younger players. The setting: a diner. The cast: a waitress, and the boyfriend from whom she's drifting apart. Here, much of what is idealized about American life gets turned upside-down: the comfort of a regular meeting spot, the joy of being a so-called "local" at a nearby restaurant or bar, the age-old pastime of harmless flirting between customers and staff. We meet a boy waiting for his date's shift to end, sitting idly and doubtlessly anticipating a happy outcome. But it's not to be, the conclusion clear from downbeat acoustic strumming and a wobbling slide guitar. The night ends in tension and boredom, as the male suitor is told in the final verse his waitress friend has too much to do to see him tomorrow. ‘Well, a question ain't really a question, if you know the answer too," Prine sings.

"In Spite of Ourselves"
With 1999's In Spite of Ourselves, Prine began a career phase that continued pretty much up until today. The record represented his first studio effort in about four years, and first since recovering from throat cancer. Many of Prine's subsequent albums are marked by duet work, and the title track for this collection, the sole song written by Prine here, shows the ease with which he handles the duality of two conflicting voices. The star, however, is Iris DeMent, who brings an ol' fashioned country lilt to counter Prine's lived-in gruff. Throughout their traded verses, Prine and DeMent paint slightly opposing but loving views of a marriage. This is a couple that knows each so well that they also adore each other's wrongheaded conclusions. And can laugh at them. "She gets it on like the Easter Bunny," Prine claims. "I caught him once and he was sniffin' my undies," DeMent counters.

"The Lonesome Friends of Science"
A highlight on Prine's new album, this track shows how he has long taken the big, the important, and the global, and turned such matters into something more intimate and personable. Playing a storyteller rather than a lecturer, Prine on "The Lonesome Friends of Science" allows the song to come off as a jab against climate-change deniers and do so in a way that alludes to the muddled political messages aimed at overworked Americans. The narrator doesn't seem to have an opinion as much as distrust, and therefore resorts to believing in Farmer's Almanac-like tales. Prine sings, "My dog predicts hurricanes/She can smell a storm a mile away/That's all the news we have today." His voice is now thinner, and his singing sparser. Soft-as-candlelight acoustics reflect these conditions, but also convey a lonelier tone. Call it a lament for the loss of reason.

"Lake Marie"
An absolutely epic albeit devastating song, and one that captures the innocence lost of not just a couple but a nation. Produced by Howie Epstein, the bassist of Tom Petty and the Heartbreakers fame, the 1995 song possesses a jangly bounce and a casual sing-song delivery. Guitars sway and a harmonica blossoms, and Prine sets up the listener for a lighthearted yet picturesque tale of suburban America. We learn how lakes in the Midwest received their name, and then we meet a couple who fell in love by said bodies of water. But the striking third verse jolts us. Suddenly, the beautiful lakes in the woods are marred by tragedy. "You know what blood looks like in a black and white video?" Prine asks, as he tells of seeing the once-peaceful setting transform into a crime scene on the evening news. In turn, a place of wonder has become the setting of an unspeakable horror, and what was once taken for granted can no longer be.

Photo credit: Danny Clinch