“Either Way” opens Sky Blue Sky with a melancholic simplicity, foreshadowing the the rest of the album. Similar to Tweedy’s narrators in the remaining tracks on Sky, “Either Way” is told from someone who clearly struggles to be heard, to be loved and to be worthy of love.

Rolling Stone magazine’s Rob Sheffield describes the song as:

a slight ditty with the acoustic-guitar intro from “Blowin' in the Wind.” There’s a string section, plus a really, really terrible guitar solo that sounds like a Pat Metheny clone grooving to the Weather Channel, which makes sense, since Tweedy is singing about the sun, clouds, etc…the vocal is so straightforward you wonder if Tweedy’s putting you on, but he’s not — he’s reveling in clarity and simplicity

Other critics, such as Pitchfork’s Rob Mitchum, express a more negative impression. Mitchum opines that:

the drowsy opener “Either Way” sleepwalks through a list of indecisive sentiments (“maybe you love me, maybe you don’t”) before breaking for a Cline solo that’s straight-up Weather Channel Local on the 8s.