This is a doozy of a task, folks, but so it is with picking a best five albums in any genre. With the full awareness that passions can run high when you get to ranking good music, and fans of alt-country and Americana are going to have their own favorites, undoubtedly, I’m going to focus on five albums that will at least give you an excellent handle on what this whole “alt-country” thing is, and what it sounds like not only at its best, but at its most seminal. Also, note that these are all products of the modern era of alt-country—although from the front edge of dynasty, without a doubt—rather than nods to the classics of a generation before.

The Jayhawks Hollywood Town Hall 5. The Jayhawks, Hollywood Town Hall (Warner Bros, 1992)
With a total absence of presumption or pretense The Jayhawks’ third album, their major-label debut, established a sonic touchstone for core Americana that provides a one-stop reference point to this day. Through the course of ten tracks that are simultaneously spring-dew fresh and favorite-jeans familiar, signers and songwriters Gary Louris and Mark Olson blend dirt-floor rootsiness and back-alley gumption to define Generation X’s perspective on heartland America. In equal measures smooth and textured, tracks like “Crowded in the Wings,” “Waiting for the Sun,” and “Settled Down Like Rain” combine folk, rock, country, and a dash of rural blues so thoroughly that the individual elements surrender themselves to the cohesion of the brew. Throughout, Louris’s lead guitar work speaks to the heart of this mutt of a genre: rather than chicken-pickin’ country-fried workouts, he rips out down and dirty blues-based rock solos from a ’60s Gibson SG Standard, while Olson chops out the rhythm on a chugging acoustic. Hell, even the cover captures the cultural contradictions at the heart of the Americana and alt-country movement by featuring the band posed in front of a peeling, clapboard construction somewhere in nowheresville, with the unlikely legend “Hollywood Town Hall” painted above its door. We’re not in Kansas any more… or are we?

Wilco Being There4. Wilco, Being There (Reprise, 1996)
Okay, this is where the shouting match starts—and this just among Wilco fans—but stick with me. While perhaps not Wilco’s very best album, nor the band’s most alt-countrified offering, Being There is a stunning statement that shows a band in transition, and therefore bridges the chasm from roots music to the more eclectic, even experimental post-modern concoction that Wilco is known for today. No, you can’t really even call Wilco circa 2008 an alt-country band any more; on the other side of the coin, the debut, 1995’s AM, was undoubtedly their seminal offering from a purely alt-country perspective, but frontman and songwwriter Jeff Tweedy himself has said that recording was really just what would have been the next step in the road for Uncle Tupelo if Jay Farrar hadn’t decided to break up the band. Over two full discs, Being There establishes Wilco as its own force, and one to be reckoned with, while making the giant leap from the despair and cacophony of opener “Misunderstood” to the punch-drunk optimism of closer “Dreamer in My Dreams”, via the steam-train twangfest of “Forget the Flowers,” a song what would have done Gram Parsons or the Flying Burrito Brothers proud.

Whiskeytown Strangers Almanac3. Whiskeytown, Strangers Almanac (Outpost, 1997)
For the Whiskeytown choice—and Whiskeytown has got to be in here—I’d almost concede it’s a toss up between this one and Faithless Street. If anything, though, I’d say Stranger’s Almanac displays a band that has matured, that finally knows what it’s trying to do, and does it. Which is not to say young Ryan Adams and friends had settled down any here, for sure. Swaggering from songs that could really be more Replacements-with-a-drawl—“Yesterday’s News” or “Waiting to Derail”—to rugged but unashamed country, replete with fiddles and wailing steel guitar, of “Inn Town,” “Excuse Me While I Break My Own Heart Tonight," or  “Dancing With the Women at the Bar.” Adams’s plaintive, bourbon-scorched delivery presents an artist that’s world-weary beyond his years, while Caitlin Cary’s evocative harmonies —and the band’s comfortably loose performances—help propel it all far beyond the megalomania that seems to perpetually threaten to envelop Adams’s solo work. 

Son Volt Trace2. Son Volt, Trace (Warner Bros, 1995)
While I docked Wilco’s AM for being too much a continuation of the Uncle Tupelo groove, I’m elevating Jay Farrar’s post-UT band’s debut effort, Trace, to its silver-medal position through a seemingly illogical inversion of the same thinking. As important as Jeff Tweedy was to the whole formula and, therefore, to cementing into place the cornerstone of contemporary alt-country, the entire vibe of Uncle Tupelo is carried through more thoroughly on this album, which confirms—to me, anyway—that Farrar’s voice and vision really were the dominant factors in the sound. It might seem ironic, then, that Wilco has gone on to be a bigger name than Son Volt, but I’d argue that that is precisely the point here: by sliding sideways out of this admittedly eclectic, anti-populist genre, Wilco has opened itself up to other ears. Farrar and Son Volt, meanwhile, for the first few albums at least, continued to mine the alt-country motherload, even if doing so ultimately capped their potential popularity. But back to the music … Trace is rich, earthy stuff, from start to finish, and from tune-one Farrar establishes a mood that is rare for being simultaneously new and timeless, comforting and edgy. This album also represents one of the easiest blends of acoustic and electric textures you’ll find, and that in itself helps to frame the ethos of alt-country. It segues unapologetically from the mournful lope of “Tear Stained Eye” to the grinding, overdriven rock of “Route” without blinking, while the anthemic “Live Free or Die” pulls the same tricks all within the confines of the same song. With energizing guitar, lap-steel, and fiddle work from Dave Boquist, and tasteful, atmospheric harmonies from bassist brother Jim Boquist, all to a pulse pinned down by drummer Mike Heidorn, this is one of those albums that really blooms with repeated listenings, and once it gets you, hooks you but good.

Uncle Tupelo Anodyne1. Uncle Tupelo, Anodyne (Warner Bros, 1993)
Sure, their earlier album No Depression might have christened a musical movement (or at least the voice of that movement, the recently defunct music magazine of the same name), but Anodyne more thoroughly displays the artistic heights that Tweedy and Farrar had attained within their own self-defined genre, right before the wheels fell off the wagon. The band’s final outing is a grain silo de force, and all the more impressive for that fact that it was recorded entirely live in the Austin, Texas, studio that birthed it. Through 12 tracks that are in turns—and sometimes simultaneously—uplifting and forlorn, Anodyne bundles up the angst of urban, suburban, and rural America to distil it into something that is ultimately hopeful, while ever aware of its rust-belt dilapidation, its dustbowl despair. The songs “We’ve Been Had” and “Fifteen Keyes” express, back to back, the frustrations of a lost generation seeking a music that fits its mood, while the rollicking “Long Cut” and “Chickamauga” speak to the simple, surprising strength to be found in place, roots, and the pure joy of heading out, and heading back again. If you’re curious about this thing called alt-country but only have time to bend your ear to one album, this is the one to spin. Seminal stuff, by definition.