Carrie & Lowell has been touted as one of—if not the best—Sufjan Stevens albums to date, and songs like the gorgeously lush "Should Have Known Better" make it abundantly clear why. In dealing with his estranged mother's death, "Should Have Known Better" touches on a number of things: his depression, heartbreaking memories of his mother, and, ultimately transcendence from his sorrow.

This latter part is reflected in the song's production, where hopeful and bright electric keyboards follow melancholic acoustic guitar, pointing towards acceptance and peace.—Joyce