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10 Best Wilco Songs

Wilco
Larry Busacca, Getty Images
Wilco's songs have been combining alt-country, Americana, neo-folk and alt-rock into a wonderful audio concoction for about 18 years now. The Chicago outfit rose out of the ashes of their previous incarnation, Uncle Tupelo, and have sustained a career of pushing musical boundaries whenever they can. Throughout the years, they've released eight studio albums. Based on success, reader favorites and personal opinion, we've narrowed that down to the 10 Best Wilco Songs.


Wilco Can't Stand It
10

'Can't Stand It'

From 'Summerteeth' (1999)
 
 

Coming in at No. 10 on our Best Wilco Songs list is 'Can't Stand It,' from Wilco's third studio album, Summerteeth' -- though the record was met with lukewarm sales, moving only 200,000 copies. The band and executives at Reprise Records agreed to remix 'Can't Stand It' to make it more "radio-friendly." Portions of the bridge were removed and bells added, which made the song sound more polished.

 
Wilco War on War
9

'War on War'

From 'Yankee Hotel Foxtrot' (2001)
 
 

Wilco's fourth studio release, 'Yankee Hotel Foxtrot,' is often regarded as one of the best albums in the 2000s. The single 'War on War' saw Wilco delve deeper into psychedelia and carefully blending it with indie-folk. 'Yankee Hotel Foxtrot' was a prime example of how strange the music business could be. Reprise Records refused to release the album and granted Wilco the rights to the record. Yet Nonesuch Records, who shared the same parent company with Reprise in Warner Bros. Records., eventually put out 'Yankee Hotel Front.'

 
Wilco I Might
8

'I Might'

From 'The Whole Love' (2011)
 
 

2011 saw the release of Wilco's latest album, 'The Whole Love,' in which the Chicago rockers started experimenting with different sounds again after their last two albums stayed pretty consistent sonically. 'I Might' is a bouncy Wilco song that's complemented by a quirky organ reminiscent of the Doors' 'Light My Fire.'

 
Wilco I'm a Wheel
7

'I'm a Wheel'

From 'A Ghost Is Born' (2004)
 
 

After the unexpected success of 'Yankee Hotel Foxtrot,' Wilco took a different approach with the follow-up 'A Ghost Is Born.' It was their first album to be recorded using audio program Pro Tools before being played live. 'I'm a Wheel' is one of the more straightforward rock songs from Wilco, sounding like a lost Sonic Youth track. This is definitely a good thing -- and that's why it's No. 7 on our 10 Best Wilco Songs list.

 
Wilco Outtasite Outta Mind
6

'Outtasite (Outta Mind)'

From 'Being There' (1996)
 
 

After the disappointing performance of Wilco's debut album, 'A.M.,' the group decided to shed their alt-country vibe on the next disc, 'Being Here.' It produced Wilco's biggest hit to date, the post-breakup anthem 'Outtasite (Outta Mind).' Wilco added keyboards to their repertoire with the addition of multi-instrumentalist Jay Bennett. The music video for 'Outtasite (Outta Mind)' featured the band skydiving while performing the song.

 
Wilco I Am Trying to Break Your Heart
5

'I Am Trying to Break Your Heart'

From 'Yankee Hotel Foxtrot' (2001)
 
 

No. 5 on our list of the best Wilco songs comes from the classic 'Yankee Hotel Foxtrot' album. The seven-minute opener about of fading love in 'I'm Trying to Break Your Heart' exemplifies what many couples go through who refuse to accept that their relationship has run its course. Clashing tuned keys and reserved guitars and drums help make frontman Jeff Tweedy's melancholy lyrics stand out. "I'd always thought that if I held you tightly / You'd always love me like you did back then," sings Tweedy. Don't we all think that at some point in our lives.

 
Wilco A Shot in the Arm
4

'A Shot in the Arm'

From 'Summerteeth' (1999)
 
 

Jeff Tweedy was going through difficult times during the recording sessions for Wilco's third studio album, 'Summerteeth.' Several songs off the record were reportedly about his marital problems with wife Sue Miller. Tweedy expresses how he feels Miller has changed over the course of their marriage in the Wilco song 'A Shot in the Arm.' "What you once were isn't what you want to be anymore," Tweedy accuses repeatedly at the end of the track.

 
Wilco You Never Know
3

'You Never Know'

From 'Wilco' (2009)
 
 

'You Never Know,' which comes in at No. 3 on our 10 Best Wilco Songs list, is the lead-off single from the band's 2009 self-titled album. The lush guitar and piano elements are eloquently mixed together for a Beatles-esque vibe. Some even call the track a tribute to late Beatles guitarist George Harrison. 'You Never Know' is a prime example of Wilco fusing Americana with their alt-country roots.

 
Wilco Box Full of Letters
2

'Box Full of Letters'

From 'A.M.' (1995)
 
 

When Wilco released their first album since their Uncle Tupelo days, 1995's 'A.M.,' the band kept its alt-country sound intact. 'Box Full of Letters' can be interpreted as a breakup song, with lyrics like, "I got a lot of your records / In a separate stack" and "Some things that I might like to hear / But I guess I'll give 'em back." However, many fans speculate the track is about the dissolution of Tweedy's friendship with former Uncle Tupelo bandmate Jay Farrar. Regardless of the subject matter, 'Box Full of Letters' lands at No. 2 on our best Wilco songs list.

 
Wilco You and I
1

'You and I'

From 'Wilco' (2009)
 
 

When Wilco released their self-titled seventh album in 2009, fans were treated to the very first duet to ever be featured on one of the band's records. 'You and I' features Canadian indie songstress Feist, whose reserved vocals intertwine perfectly with lead singer Jeff Tweedy's. Wilco and Feist met at the 2008 Grammy Awards and learned their mutual appreciation for each other's music. This meeting of indie rock royalty makes 'You and I' the Wilco song that tops our list.

 

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