Though recorded before September 11, Loudon Wainwright III’s new record seems to have an eerie relationship with the dreadful day. The record just so happens to be about grief. Inspired in large part by the death of Wainwright’s mother, the songs on Last Man on Earth face loss with tender reminiscence (“Out of Reach” and “Homeless”), brash stoicism (“I’m Not Gonna Cry Today”) and sad self exploration (“Living Alone” and “Missing You”).

The rainbow of emotions, as if intersecting a prism, come out as one heavy mood. But as anyone who has checked in with Mr. Wainwright, 55, at any point along his 22-album career would guess, the new songs, even at their darkest, never take themselves too seriously. Group him with Randy Newman or John Prine—songwriters who can skillfully and, somehow, appropriately weave humor, introspection, politics and pain into multi-textured music.

Fans looking for a stylistic leap from Wainwright, something beyond his standard acoustic guitar and voice format, can skip Last Man on Earth. The music varies little from previous albums. But if it’s simple, finely wrought folk songs you crave, look no further.