Entertainment Music Top 10 Wilco Songs Wilco's Greatest Songs Ever Share PINTEREST Email Print Raphael Dias/Contributor/Getty Images Music Rock Music Top Picks Top Artists Holiday Music Pop Music Alternative Music Classical Music Country Music Folk Music Rap & Hip Hop Rhythm & Blues World Music Punk Music Heavy Metal Jazz Latin Music Oldies Learn More By Tim Grierson Updated June 11, 2019 Wilco isn't the kind of band who have hits on the radio, so picking their best songs can prove a little tricky. Nonetheless, the greatest Wilco tracks offer a handy overview of the band's various musical styles – there's a little country, pop, folk and indie-rock on this list. 10 of 10 "Handshake Drugs" (from 'A Ghost Is Born') Wilco - 'A Ghost Is Born'. Photo courtesy Nonesuch Because "Handshake Drugs" appeared on A Ghost Is Born, an album recorded around the same time Wilco frontman and principal songwriter Jeff Tweedy was in rehab for an addiction to painkillers, it's tempting to assume that this song is about, well, drugs. But this catchy tune is more accurately described as a search for connection – Tweedy seems to be trying to figure out his place in the world. The slowly-building discord at the end of the song mirrors the narrator's growing disillusionment and despair. 09 of 10 "Far, Far Away" (from 'Being There') Wilco - 'Being There'. Photo courtesy Reprise Stripped down to the basics – acoustic guitar, pedal steel, and harmonica – Tweedy sings about a classic theme for many a touring band: being away from the girl that you love. The spare, country-ish arrangement to "Far, Far Away" makes the listener really feel Tweedy's loneliness, as if he's about a second away from getting a tear in his beer. 08 of 10 "Please Be Patient With Me" (from 'Sky Blue Sky') Wilco - 'Sky Blue Sky'. Photo courtesy Nonesuch Sky Blue Sky is, among other things, a relationship album that chronicles the ups and downs of marriage. "Please Be Patient With Me" is one of the saddest songs in the Wilco canon – Tweedy sings sweetly to his lover, acknowledging his many faults while asking for another chance. Tenderness and intimacy suffuse this track, and Wilco give the song all the fragility of a difficult heart-to-heart talk. 07 of 10 "I Must Be High" (from 'A.M.') Wilco - 'A.M.". Photo courtesy Sire The first song off Wilco's first album, "I Must Be High" stomps out of the barn with country-rock fervor. Jeff Tweedy details a classic scenario: an on-and-off relationship that's headed for another breakup. Wilco would go on to make more elaborate, ambitious material, but they rarely were as carefree and playful as they were here. 06 of 10 "My Darling" (from 'Summerteeth') Wilco - 'Summerteeth'. Photo courtesy Reprise Wilco incorporated pop melodies on Summerteeth, but that didn't mean the songs were happy-go-lucky. Take "My Darling," a combination of chamber-pop intricacy and Beach Boys-style melody, in which the narrator serenades his newborn baby to sleep, hoping that he can be a good father. The soaring music feels both gorgeous and wistful as if the family's future hangs in the balance. 05 of 10 "Red-Eyed and Blue" (from 'Being There') Wilco - 'Being There'. Photo courtesy Reprise Being There captured Wilco at an early stage in their career when their longevity was far from assured. On one level, "Red-Eyed and Blue" is a straightforward country ballad about loneliness, but it's hard not to read deeper into the lyrics, interpreting the song as a snapshot into Tweedy's uncertain mindset. Looking at the song this way, "Red-Eyed and Blue" is about the isolation of the recording studio and the pressure to create something meaningful. 04 of 10 "Poor Places" (from 'Yankee Hotel Foxtrot') Wilco - 'Yankee Hotel Foxtrot'. Photo courtesy Nonesuch Considering that it's generally considered Wilco's best record, Yankee Hotel Foxtrot contains many fan favorites. This pick is one that's less popular but does the best job at merging the album's sonic experimentation with Tweedy's skill at crafting yearning lyrics. "Poor Places" doesn't make much literal sense – it has something to do with the singer’s father, a broken jaw, and a backyard – but the song's atmosphere of isolation and longing is so potent that the surreal verses begin to feel logical in some deep, unconscious way. Plus, the swirl of piano, guitar and studio trickery is hypnotizing. 03 of 10 "I'm Always in Love" (from 'Summerteeth') Wilco - 'Summerteeth'. Photo courtesy Reprise If you could turn the thrill of spring's restorative power into a song, it might sound like "I'm Always in Love." Driven by Ken Coomer's bouncy drums and Jay Bennett's euphoric keyboards, the music feels like an irrepressible ode to romance, but Jeff Tweedy's lyrics tell a different story – he confesses to having a "heart full of holes" due to his willingness to fall in love too quickly. That tension between optimism and fearfulness gives "I'm Always in Love" its crackle. 02 of 10 "Either Way" (from 'Sky Blue Sky') Wilco - 'Sky Blue Sky'. Photo courtesy Nonesuch After two albums of studio fussing, Sky Blue Sky represented a pared-down approach, and the first track, "Either Way," proved how rewarding the strategy turned out to be. Subtly layering in strings and guitars, Wilco delivered their definitive relationship song, one that encapsulates the doubt, hope and abiding love that any long-term couple experiences. "Either Way" is either romantic or tragic, depending on your perspective, but either way it's a beautiful song. 01 of 10 "California Stars" (from 'Mermaid Avenue') Billy Bragg & Wilco - 'Mermaid Avenue'. Photo courtesy Elektra Wilco's finest moment didn’t come on any of their studio albums. Instead, it resides on Mermaid Avenue, a project that brought together the unpublished poetry of Woody Guthrie with the music of Wilco and Billy Bragg. Wilco responded with their most impossibly gorgeous song, "California Stars." Guthrie's lyrics tell of putting your cares aside and just spending some time with your lover, but Wilco amplifies the sentiments with dreamy folk-rock that sounds positively moonlit. And even though Tweedy didn't write the words, he sings them as if he did, folding them into his usual concerns about love and contentment.