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The album marked a creative shift from Yo La Tengo's previous work, blending atmospheric and ambient sounds with their famous noise jams. Painful features a much more melody-driven Yo La Tengo in its hazy, dream-like songwriting.
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.
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."[14] Reflecting on it in a 20th anniversary review, Spectrum Culture's Rodger Coleman called it "revelatory, ageless and sublime." He saw it as the album "where they first came together as a real band," as well as showing "a substantial refinement of sound and approach."[15]