In every way possible, We Should Have Never Lived Like We Were Skyscrapers is a memorial to Chin Up Chin Up's bassist Chris Saathoff. Hours after finishing demos for the album, Saathoff was struck by a drunk driver and killed. It's an event that could have easily brought an end to the band, but encouraged by support following two benefit performances for the Chris Saathoff Foundation, the band decided to continue on.

Seeking to involve Saathoff in the recording process, Chin Up Chin Up recorded around the bass tracks from the demo when possible and had guitarist Nathan Snydacker double on bass to perform lines based on those created by Saathoff during practice sessions. Possibly a result of this inspired methodology, the many layers present on the tracks often seem to spiral around each other creating a sensation similar to what may be experienced during a walk on a crisp winter morning. No one instrument takes precedence over another and the airiness of the arrangements allow parts to be further examined individually as well as part of the whole; Discovery of new subtleties to the compositions is almost guaranteed with each listen.

While completing We Should Have Never Lived Like We Were Skyscrapers may offer some closure for the band as it has learned to cope with the loss of Saathoff, it will hopefully be just the beginning of things to come from the Chicago band. "All My Hammocks Are Dying", the only song written after Saathoff's death, continues to demonstrate Chin Up Chin Up's ability to build intricate layers but without the bass, instead utilizing Greg Sharp's keyboards to fill in the low end.