The Many Hairstyles Of Jake Gyllenhaal

2. The Lover Boy - Love & Other Drugs

The Lover Boy is a tricky one to achieve: it requires portraying a look of wildness that will imply a man who's subject to massive sways of emotion and romance (and who's a master in the sack), mixed with an expert level of control and gel-use to make it all stay in place. To be honest, the "wild" part of the equation is merely an illusion; it is in fact a very carefully calculated version of wildness that infers an untamed man, but actually harbours a very underwhelming sissy-boy. The lid makes it seem like he's too hot and too cool to care about his hair, but in reality it's all he cares about and spends hours perfecting it. The whole thing is completed by a hint of stubble that's trying to say "oh yeah, I just got up this morning and didn't bother to shave", but actually ends up saying "I spent over $200 on a high-end shaver so I can look like this every day".
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