Fiona Apple's album, ‘When the Pawn…’, transcended mainstream music at its time of release, in 1999. Her lyricism cuts deep, riddled with dark themes. This album has earned several achievements, both in Grammy Awards nominations and receiving Platinum by Recording Industry Association of America, truly marking its place in alternative/indie music history.

This album marked Fiona's second studio release following her debut album, 'Tidal' in 1996. Unfortunately, Fiona has faced criticism for her melancholic disposition, which has been attributed to the message of her songs. In fact, during her acceptance speech at the 1997 MTV Awards, many misunderstood her point about the inauthenticity in the music industry. Fiona has even been accused of pretension with this album, as its title is a 90-word poem that held the Guinness World Record for the longest album title until 2008. One of the lyrics from the song 'To Your Love' appears to be directed at a hypothetical lover she is quarreling with. Still, it also seems to be a statement to her critics who try to silence her, "Here's another speech you wish I'd swallow, another cue for you to fold your ears." Unfortunately, female artists in the music industry who write about tough topics often face criticism, they are accused of being pretentious and being too emotional. On the other hand, male artists who do the same are celebrated for their emotional intelligence.

This album flows well and concisely, with a total time of 42 minutes. Songs like ‘Paper Bag’ and ‘Fast As You Can’ that appear on this album have become very popular. She frantically sings “You say you don't spook easy You won't go But I know And I pray that you will” on her song ‘Fast As You Can’, she begs her lover to leave her because she knows she will hurt them. Women are usually characterized as being good-natured and kind, she isn’t afraid to be the bad guy and admit her faults. Her songs are vulnerable and she is open about her thoughts. Her vocals are powerful in the opening song, ‘On the Bound’, she’s mad at her codependency and repeatedly sings “You’re all I need” in the beginning. In many of her songs, she is refusing, she is pushing away and does not want to be tied down. She’s pleading to be left alone, recognizing her own mistrust and animosity. The instrumentals in this album are raw and add to her powerful voice, piano is incorporated heavily along with guitar, and there are a lot of rock influences. The last song ‘I Know’ is a beautiful piano ballad with soft vocals, deeply contrasting the rest of the album. She takes a completely different stance than she has prior, she is done fighting and has fully resigned. “And I will pretend That I don’t know of your sins Until you are ready to confess But all the time, all the time I’ll know, I’ll know” It seems she already knew of his infidelity and allowed him to eventually tell her while she had already rescinded her feelings about the relationship.

Although differentiating herself from more mainstream artists Fiona Apple is far from underground and has several critically acclaimed, hit songs. This specific album of hers is still relevant to this day, ‘When the Pawn…’ achieved Platinum on March 26, 2020 by the Recording Industry Association of America. It also received a Grammy nomination for Best Alternative Album in 2000. Another song on this album, “Paper Bag”, has received a Grammy nomination for Best Female Rock Vocal Performance in 2001.

“When the Pawn…” stands out from the musical landscape of its time. Fiona Apple has made history as an artist and more specifically as a female songwriter and vocalist in the Alternative Music scene.