Released on 20 September 1994, "Whip-Smart" was the second studio album by American singer-artist Liz Phair, the album was a critical failure but succesful debuted on No. 27 at Billboard 200, the album spawned three singles "Supernova", "Whip-Smart", & "Jealousy".
The expectations ran high for Liz Phair's sophomore release. Phair's debut album had sold over 200,000 units by the spring of 1994 and was Matador's most successful release so far. The success of Exile in Guyville prompted many major labels to seek a distribution deal with Matador, most saliently Atlantic Records, which would form Phair's next album deal. As a result, Whip-Smart was one of the most anticipated albums of the year. Danny Goldberg, then-president of Atlantic Records, predicted that the record would "hit gold quickly".
described it as particularly difficult to make because at the time she didn't have many songs that weren't about the music industry, which displeased her manager. In fact, a substantial number of tracks on the final album (namely, "Chopsticks," "Shane," "Go West," "Whip-Smart," and parts of "Jealousy", previously known as "Thrax") were songs already written in 1991. Whip-Smart took about one month to record. The album was recorded in two distinct sessions: the first in August 1993 in Chicago, and the second in February 1994 in the Bahamas.
Guitarist Casey Rice described the initial sessions at Idful Studios in Chicago as subject to many distractions, such as "the phone ringing, people dropping by the studio, and so on". Phair wanted to move recording to New York City, but due to financial constraints, the band ended up continuing with Compass Point Studios in Nassau, Bahamas instead. The same team that worked on Guyville worked again on what would become Whip-Smart. The album was recorded and mixed by Brad Wood, with the assistance of Casey Rice. Wood characterized the recording process as very much spontaneous, saying that "[Liz would] bring in a song and we'd record the whole thing that day. I'd have to write a drum and bass part right on the spot." There was, however, pressure to improve on the sound of the previous record, to meet the expectations of Phair's newly formed fanbase.
The album is a chronicle of the beginning, middle and end of a relationship: "a rock fairy tale, from meeting the guy, falling for him, getting him and not getting him, going through the disillusionment period, saying 'Fuck it,' and leaving, coming back to it." Phair also described the sound of the album as more confident and playful and less frustrated, tense, and sexual than it was her predeccessor album.
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