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In light of some breaking hair-related news involving future fugitive Katie Holmes, we must admit that we’ve underestimated the Scientology prisoner. As the Daily Mail reported over the weekend, Broadway’s least-alluring celebrity rookie recently chopped off even more of her already chin-grazing bob, and even dared to pull out those hair curlers in what could be the beginning move in a new strategy to finally flee the Knights of Hubbard. Though Kate’s "boyish" cut may backfire, it’s a clever plan nonetheless. Below, we provide five of the best examples of drastic 'do-caused catastrophes directly linked to highly publicized breakups, from Jennifer Aniston’s self-conscious bob that led to Brangelina, to Cameron Diaz’s unfortunate goth dye job that failed to inspire any future sex or love sounds from Justin Timberlake:

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Though Cameron told Jay Leno she "just loved" her new brown hair back in 2006, Timberlake didn't appear to share the sentiment, initially moving on to very blonde ScarJo, then the more natural brunette Jessica Biel. But maybe Diaz should have seen it coming - in the same Leno interview, she said her new dye job was attracting more "introspective" men. JT may be many things, but pensive? And as hard as we try to erase the memory from our collective mind, the sight of Smartest Dumb Blonde In The World, Jessica Simpson, sporting those dark hues while desperately installing her chin on John Mayer's shoulder did little to inspire the crooner's signature O-face.

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Yes, a nanny and various False Terribles are mostly to blame for the split between Jude Law and Sienna Miller, but only months after cutting off her Alfie-saving blonde waves for the underrated Factory Girl, Law just happened to fall for the long straw-colored tresses of the otherwise aesthetically incomparable nanny. Similarly, Gigli is mostly at fault for ruining what may be the union responsible for all Brangelina and TomKat-style celebrity couple name combos: Bennifer. But that awkward curly housewife cut didn't help. Neither did Aniston's self-proclaimed "regretful" decision to cut her trademark Rachel off during what we would later learn to be her final days of marriage with Brad Pitt — after all, we all know how that story ended.

[Photo credits: Getty, Splash, Beauty And The Bath]