In the album's liner notes, David Gates — the Pulitzer-nominated author (Jernigan) and former senior arts writer for Newsweek — sets the tone for Weary Things: "What [Friedman] sees through his windshield isn't Greil Marcus's Old Weird America, but the weird new America where the pastoral is no longer pure." In "Locked Out of the Building," a thumping, electric John Lee Hooker–inspired lyrical boogie, "a little country store five miles past the light/is more expensive than Brooklyn."

In "Freddy's Backroom," the third generation Brooklynite ("My grandpa was eating at Junior's before they served cheesecake," offers Friedman) writes a mournful ode to his favorite neighborhood dive bar, which will soon be demolished. The quiet neighborhood where Friedman lives will be the future home for the Brooklyn Nets (currently the New Jersey Nets), complete with a Frank Gehry arena and four forty-plus story high-rise luxury towers. "The urban pastoral is vanishing too," observes Gates.

Throughout the record — produced by label-mate, long time crony, and Charlottesville, Virginia-based songwriter and guitarist Paul Curreri (The Velvet Rut, Songs for Devon Sproule) — Friedman reveals an abundance of stunning realities that make him weary. The album's first track is the somber "I Miss Being Broken, Lowdown, and Alone," described in the liner notes as "a wistful look back at being young, miserable and lost." Says Gates, "the ambivalence is so acutely balanced that a breath would start it rocking." On the plaintive "Idaho," Friedman longs to travel to some of his favorite wide-open spaces: Idaho, New Mexico, and Colorado, to list a few. "I'm gonna get back there/if I ever get the time," he sings. "Road Trippin'" is presented on this collection twice — once as the rollicking rockabilly version that has become a favorite at live performances ("People dance on the tables," declares Friedman), and another as "Road Trippin' Daddy," offered as a somber lullaby. Friedman, a devoted husband and father of two, has mixed feelings about the amount of time he spends on the road. "If you see me packing/There's a good time to hide my keys," the artist sings. The contrasting treatments color the song's identical lyrics with a mood of defiance and cockiness on the one hand, guilt and regret on the other, respectively.

In the end, Friedman's portrayal of himself as a weary artist, poet, observer, traveler, and family man is varnished with a glaze of optimism. Perhaps the most sparsely arranged composition on the album, "Weary Apology" offers clues to the songwriter's sense of fulfillment, and a desire to keep working and dreaming, no matter the costs or how tired he gets. "I don't need to make a weary apology," he sings, "I spent a week in a beach house in Aquinnah last June/took a staircase to a roof deck and a ladder to the moon."

The album's ferocious closer, "The Friedman Holler," was unknowingly recorded at a live performance in Chicago, Illinois, and exhibits all of the reasons why this "hot live act" (NPR) has garnered such abundant worldwide praise and a growing following. A theme song in the tradition of Jerry Lee Lewis' "Lewis Boogie" or Carl Perkins' "Perkins Wiggle," the tune lays out Friedman's "Art Country" manifesto: "Art and country is for lovers/whatever color your collar."