"6th Avenue Heartache" is a song by American rock band The Wallflowers. It was released in April 1996 as the lead single from their 1996 debut album Bringing Down the Horse. The song became their first hit, peaking at number 8 on the US Modern Rock Tracks chart, number 10 on the US Mainstream Rock Tracks chart, and number 33 on the US Hot 100 Airplay chart. Though the song was a hit on rock radio, it was overshadowed by its follow-up single, "One Headlight." The background vocals in this song are by Adam Duritz from Counting Crows.

Jakob Dylan, the band's lead singer, wrote the song when he was eighteen years old, and considers it the first real song he had written. It was meant to go on their self-titled first album, but the record company would not allow it. The lyrics are based on Dylan's own experiences while living in New York City, in particular the story of a homeless man who would sit outside his window and play the same songs every day. One day the man was gone, but his things were still there, until gradually people started taking them.

Mike Campbell from Tom Petty and The Heartbreakers played the slide guitar on the song, though he recorded the track in his own studio, and never even met the band members.

The video, shot in New York, was directed by movie director David Fincher, known for such films as Se7en and Fight Club. There is a slight error in the video: Rama's Cafe, portrayed as a meeting place for the band, was actually on 281 5th Avenue, not 6th Avenue. The building was eventually demolished and a new apartment building is in the process of being constructed on the site.

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