Ultra Records had approached Grandaddy frontman Jason Lytle via his management some time earlier with the idea for him to compile a mixtape, and he decided to include tracks that he considered "sleeper hits", identifying a common theme: "They all seem to have pretty conventional and familiar chord progressions. They all have vivid imagery for me with their words. There also seems to be a bit of sadness, but not necessarily despair."
AllMusic's Matt Collar stated the album "plays like a K-Tel commercial for Gen X sad-sackism", calling it "pretty cool". Brian Howe of Pitchfork wrote "for the most part, the songs [Lytle] selected sound quite a bit like his own band. Lush yet sleek and slightly sterile is the dominant style of Below the Radio".