Wilco's career restrospective What's Your 20? favors songs obsessed with drugs, heartache and identity crisis

A new generation of music fans checked the mirror for gray hairs last November when Wilco dropped their career retrospective double album, What's Your 20? Essential Tracks 1994-2014. The imaginative, genre-leaping instrumentation and thought-provoking poetry in Jeff Tweedy's lyrics – which can be staggeringly simple or epiphany-inducing from their complexity – launched the band to mainstream success at a time when many artists in the alt-country realm played it safer and truer in a more sensible, timid attempt to gain steam the old-fashioned Nashville way.

Wilco's experiment paid off, winning a zealous fan base as well as critics' hearts with early releases like Being There (1996) and Summerteeth (1999), then steamrolling through the 2000s with success after success on releases like Yankee Hotel Foxtrot (2002), A Ghost Is Born (2004), Sky Blue Sky (2007) and their last full-length, The Whole Love (2011). Now celebrating 20 years since A.M. debuted Tweedy's then-hotly anticipated band, the retrospective is adequately fogged out, bogged down and heart-cogged over the course of 38 tracks.

The songs are organized in clumps by album, and What's Your 20? presents these bundles in order of release. Priority is given to earlier albums, with more songs represented off each, betraying a nostalgia or sentimentality for songs that set the stage for Wilco early on, like "Misunderstood" (Being There), "Via Chicago" (Summerteeth) and even the later "Jesus, Etc." (Yankee Hotel Foxtrot). These three albums take up half of What's Your 20?, which should appease their longtime fans, but it also suggests later releases somehow stuck a little less, despite fully committing to Wilco's now tried-and-true thematic formulas.

In the band's typical country-leaning fashion, if you're looking for love, the song selection finds it in all the wrong places, favoring catalog standouts focused on heartache and dealing with being an outcast over more romantic songs. "I'm the Man Who Loves You" does make the cut, playing nicely since it seems to be a prequel to A.M.'s "Box Full of Letters" (also featured). Being There's "I Got You" is the album's first straight-up love song. But two-thirds of the album's songs dwell on breakups, isolation and drug culture.

Tweedy's tug of war between life-giving and destructive little fixes appears throughout Wilco's catalog, often used to feed into moments of self-doubt and existential confusion, most obviously in songs like "A Shot in the Arm" (Summerteeth) and "Handshake Drugs" (A Ghost Is Born) where Tweedy cries, "If I ever was myself, I wasn't that night." There are also the casual drug references that put a stoner stench on tracks like "I Must Be High" (A.M.) and "Heavy Metal Drummer" (Yankee Hotel Foxtrot), helping to craft a more relatable dude narrator from the easily estranged, flawed and abstract poet behind Wilco's primarily imagery-dense songwriting.

While sex and drugs sell, an undersung aspect of Wilco's lyrics is this meta quality where certain songs discuss how their fame, earned from songs about being misunderstood, actually conflicts with feeling so misunderstood. Listen back on "Ashes of American Flags" (Yankee Hotel Foxtrot) to lines like "I shake like a toothache every time I hear myself sing" and on "Sunken Treasure" (Being There) where rock & roll maims, tames and names the band. Then, of course, there's "Wilco (the Song)" off Wilco: the Album, and, well, while Tweedy may never be fully understood by his lovers or his fans, hey, at least we see what you did there.