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Which song fits Cherry Valance's personality in The Outsiders and why?

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A song that fits Cherry Valance and her personality is Amy Winehouse's "Love is a Losing Game." The lyrics of this song lament the hardship of loving someone, and after losing Bob, Cherry Valance would certainly appreciate the difficulties suggested by a song about loss in love. Winehouse sings that "memories mar my mind," another challenge Cherry Valance experiences as she, her friends, and Bob's family grieve their loss and wonder what Bob might have been like had he been allowed to grow up into adulthood. Winehouse sings her sad song to "a gambling man," which is a phrase that suits Bob, who gambled with his life every time he engaged with the Greasers in a hostile way. "Love is a fate resigned" is another profound thought that Cherry might be able to relate to, as her depth and thoughtfulness about life are reflected in her conversations with Ponyboy. Though Cherry is a strong character and she has an independent spirit, the loss of Bob to a violent death at the hands of another young person likely impacted her personality in an intense way, one that could easily lead her to ruminate on philosophical themes like fate and free will.

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A great song for Cherry Valance, the Soc girl who enjoys watching sunsets is "The Leader of the Pack" by the Shangri-Las.  Recorded in 1964, "The Leader of the Pack" fits perfectly with Cherry's good girl image and her predilection for bad boys. 

Cherry tells Ponyboy "I could fall in love with Dallas Winston...I hope I never see him again or I will" (46).  Like the girl in the "Leader of the Pack" song, Cherry appreciates the bad-boy image that Dally projects.  The song fits perfectly with the rift between the Socs and the Greasers, just like Cherry's clean-cut cheerleader persona matches the parents' warning against the Leader of the Pack in the song:

My folks were always putting him down

(down, down)

The said that he came from

The wrong side of town ('The Leader of the Pack")

Cherry's parents would definitely have a thing or two to say about her being with any of the Greasers.  Even Two-Bit, not the brightest of the bunch, recognizes that Cherry and Marcia's reputations could suffer from being seen in the company of Greasers. 

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