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Top Five by Tom & Rich (Webmasters)
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5.  Ilpalazzo (Excel Saga)

Evil overlords are not renowned for their bespectacled nature, presumably good opticians are difficult to fund on volcanic island hideouts.  However, Ilpalazzo's tinted pince-nez predate those of The Matrix's Morpheus, and are also worn by a character who resides underground.  We just hope the lighting's good.

4.  Robin Sena (Witch Hunter Robin)

Although a powerful witch and possibly the best Goth in anime, Robin's eyesight goes a bit ropey when she uses her powers.  In order to solve this she sports an impressive pair of old fashioned half moon spectacles whenever in full on witch hunter mode.  Rocking.

3.  Gendo Ikari (Neon Genesis Evangelion)

NERV's commander (and chief git) Gendo Ikari spends most of his time underground and in dimly lit meeting rooms.  So what type of glasses would you expect him to have?  Probably not the orange tinted ones he does sport, but there you go.  We just assume he has Glaucoma.

2.  Naru Narusegawa (Love Hina)

A common theme in romantic anime is to have stunningly beautiful woman who are secretly speccy bookworms, and Love Hina is no exception.  Naru gets in here ahead of her peers because she dares to wear her glasses outside the confines of her own house, thus defying stereotype.  The fact that the glasses are those huge thick ones that look like the bottom of two milk bottles held together with wire also swings it.

1.  Mousse (Ranma ½)

His short-sightedness may be a constant source of humour in Ranma ½, but Mousse rocks.  He not only has a pair of 'milk bottle bottom' style specs similar to those of Naru Narusegawa, but also when he turns into a duck he still keeps his glasses.   What more needs to be said?
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