[13] The album marked a creative shift from Yo La Tengo's previous work, blending atmospheric and ambient sounds with their famous noise jams.

[14] Two versions of the track "Big Day Coming" are present on the album and display the range of musical stylings Yo La Tengo works with; the first version features a simple organ melody accompanied by a soft bass counterpoint and Kaplan's guitar feedback echoing in the background, while the second version is a much more straightforward, shoegaze style with an accompanying organ solo towards the latter part of the song.

[citation needed] In recent years, Painful has become regarded as a significant step for Yo La Tengo in their discography.

In a biography of the band, AllMusic's Mark Deming dubbed it "their first masterpiece", seeing it push them "in a multitude of new directions, significantly expanding [their] palette of sounds and textures.

"[15] Reflecting on it in a 20th anniversary review, Spectrum Culture's Rodger Coleman called it "revelatory, ageless and sublime."