Retrospectively, AllMusic critic Stephen Thomas Erlewine referred to the album as "a postmodern masterpiece of sorts – albeit a mainstream, post-alternative, postmodern masterpiece. It may not be as hip or innovative as, say, the Beastie Boys' "Paul's Boutique", but it is as self-referential, pop culture obsessed, and musically eclectic." Sal Cinquemani of "Slant Magazine" highlighted the album's "quirky, stream-of-conscious lyrics" and elaborate sound collages, stating that "none of [Crow's] other full-length albums have been as consistent, immaculately produced or distinctly modern." In 1999, "Rolling Stone" selected "Sheryl Crow" as one of the essential albums of the decade. In 2002, the magazine also ranked it at number 44 in its list of Women in Rock: The 50 Essential Albums. In 2003, the album was featured in the Vital Pop: 50 Essential Pop Albums list by "Slant Magazine". In 2008, "Entertainment Weekly" magazine placed the album at number 39 in their list of Top 100 Best Albums of the past 25 years. In 2020, "Rolling Stone" ranked "Sheryl Crow" at number 475 in its list of The 500 Greatest Albums of All Time.