Songfacts®:

• Wallflowers lead singer Jakob Dylan wrote "Sixth Avenue Heartache" in 1988 when he was only 18 years old. He was living in New York City off of Sixth Avenue, having dropped out of the Parsons School of Design, where he studied painting, after just two weeks. Despite being the son of Bob Dylan, he was on his own, living by himself and spending a lot of time wandering around the city and contemplating his life. The lyric reflects images of the city and his search to find his path. This was when he decided to make music his life, or at least give it a shot.
• Dylan started putting The Wallflowers together soon after writing this song. He called in a friend he knew growing up in Los Angeles, Tobi Miller, who moved across the country and became their guitarist. They rounded out the group with musicians from the local scene and got a deal with Virgin Records. "Sixth Avenue Heartache" didn't make the tracklist for their debut album, The Wallflowers, released in 1992. Dylan had beef with Virgin, particularly their efforts to promote him as son of Bob, and the group left the label. It took a while, but they landing on Interscope and released their next album, Bringing Down The Horse, in 1996. This time, "Sixth Avenue Heartache" not only made the album but was also released as the first single. The single wasn't made available for sale so it wasn't allowed on the Hot 100, but the song got lots of airplay and topped some other Billboard charts, including Adult Album alternative and Modern Rock Tracks. The album went on to sell over 4 million copies in the US and Dylan became a reluctant heartthrob.
• Mike Campbell from Tom Petty and the Heartbreakers played the slide guitar part. There is a connection here: Jakob's dad, Bob Dylan, played with Tom Petty in The Traveling Wilburys. Tom Petty and the Heartbreakers also toured with Dylan in 1986, and Dylan co-wrote "Jammin' Me."
• T Bone Burnett, who produced the Bringing Down The Horse album, is the one who wanted Campbell to play on this. Campbell didn't have time to come to the studio, so Burnett sent him the tape, which had some open tracks along with the basic rhythm track. Mike has a studio in his house, and one afternoon when he had a few hours to spare, he plugged in his guitar, came up with a few parts, doubled a couple of things, and got a sound he liked. He sent the tape back to Burnett, and the next thing he knew, Burnett called to tell him it came out really good, and the song was on the radio with his tracks. He never even met the guys in The Wallflowers.
• In a Songfacts interview with Mike Campbell, he talked about his contribution on guitar. "I really like the one guitar line in there," he said. "It was very George Harrison sounding and I was real proud of it when I got the sound in the studio, so I was glad they used it. The funny thing is, later, I ran into George. He had a real whimsical, cynical kind of thing - he looked at me and goes, 'You know, I heard that record on the radio - you're doing me now?' He said it with a little chuckle."
• The video was shot in New York City by David Fincher. Predominantly a movie director, Fincher has directed films such as Seven, The Game, Fight Club, and the third installment of Alien.
• Pointing out how David Fincher came to direct the video, Jakob Dylan said: "You know, I don't exactly remember how it happened. He just got a tape before the record was out. He got a preview of the record - an advance copy. He had heard that this was going to be the new single, and he actually called us and said he was interested in doing it, if we were interested. So we thought about it and we were like, what else have you done."
• Adam Duritz of Counting Crows provided backing vocals. Duritz and Dylan became friends in the early '90s when Duritz was working as a bartender at The Viper Room in Los Angeles.
• This was used in the Friends episode "The One with the Fake Party" (1998) when Rachel shows up in her old cheerleading uniform to get Joshua's attention.
  
  This was also used in the 2005 Cold Case episode "Revenge."