Ever since her audacious debut, Exile In Guyville, landed in 1993, singer-songwriter Liz Phair has been cipher for a certain kind of aesthetic. She's been called "the female face of indie rock," a "slacker poet of the first degree" and a "brainy bad girl," but she forever remains America's sardonic sweetheart – as Guyville's follow-up, Whip-Smart, continued to prove in 1994. Fusing lo-fi production with a singer-songwriter sensibility, Phair helped shape what would become "indie rock" and defied expectations of what a female rock star could be.

Whip-Smart builds upon the foundation set forth by her debut, capturing the same intimate, DIY style but with slicker arrangements, multi-layered vocals and experimental sound effects. Whip-Smart is far more 90s power-pop than her first offering however. Lead single, "Supernova," dominated alt.rock radio and MTV that year, and greatly introduced the once indie darling to more mainstream audiences, even earning Phair her first Grammy nomination. Whether she's reflecting on a one-night stand to the tune of the traditional waltz "Chopsticks" or invoking the official slogan of America's westward expansion in "Go West," to get over an ex, her unflinching honesty and confessional songwriting is why an entire generation so strongly identified with her, and why she forever looms large as the alt.rock queen of the 90s.

"Nashville" is another standout track, with its hazy shoegaze intro, and features one of the best refrains on the album. Much of the latter half of the record is dominated by downtempo bedroom rock, with the exception of the full-on rocker, "Jealousy." Whip-Smart would go on to debut at No. 27 on the Billboard 200, later achieving Gold status and inspiring countless singers and female-fronted bands for decades to come.