Wow, lots of Pretty in Pink references considering it is far from my favorite John Hughes movie, but it just got a re-release so you can relive the painful yet winsome lovesickness of perpetual best friend, Duckie.
The opposite of James Spader's Steff, Jon Cryer is the devoted friend who never gets the girl but will always be there to hold her when she cries. His style may be dated, but he really did it up his way from the bolo tie to the white leather shoes.
But what do you think?