There's something about the summers in years ending in nine that inspires people to write reflective songs. Maybe it's the additional rhymes compared to seven or the end of a decade feeling, like the start of a new era. Throw in the freedom of summer, especially from the perspective of an adult looking back on the era, and it's hard not to get a little melancholy.
Unlike most Anastasio-penned songs that focus on mythical characters or feature surreal lyrics, “Summer of ‘89” appeared to be blatantly autobiographical, in this case a love song written to his wife. For some that can be a little painful, and out of the gates the song touched a divisive chord among some fans; people don’t always want the curtain pulled back to show the man behind the wizard. Others have found it rather touching that Trey is showing such a transparently vulnerable side. While it was fun to come up with theories about how and why Trey wrote this song, most of them were dashed when LivePhish’s liner notes indicated that this song was co-written with Amanda Green. This wasn’t necessarily or exclusively a private moment between Trey and Sue revealed to the world; assume that the lyrics resembled real life events at your own risk.
Musically, the song is a shuffling ballad as befitting the lyrics. The music seems to be taken from a Trey song performed on his spring 1999 tour named “Andre the Giant,” not to be confused with the different Trey song with that title that was released on Seis De Mayo. Many lines have an extra or missing syllable which adds to the feel – for better and for worse – of this being a personal song being played to the whole world. The song feels like an older man flipping back through old photographs and wishing he could be that person again until the end. Then the perspective flips.
As, “And we danced all night,” is sung, we’re suddenly in a happier jam. We’re now in the night instead of looking back at it. Trey is a goofy guitarist playing local clubs with his band, working on a song named “Reba.” Hanging with MTV and the H.O.R.D.E. tour, Clifford Ball and Big Cypress – and Coventry for that matter – all of that is just an unknowable future. It’s just Trey and his girlfriend dancing all night. The future can take care of itself.
This song is written about the band's summer in Telluride, CO. The long trail that runs to a waterfall is hidden in the mountain's side. Trey addressed the meaning of the song as an intro during the Telluride CO 8/9/10 show, stating "we are gonna sing a song about the ahh, the year after the first year we came here". Beautiful place, definitely worthy of its own song!