Head tilting... like this?
Haha, sorry. Had to do that. Bemused ostrich FTW.
Yeah, it might be having to do with glasses. Or it might be that he saw one of the LOLcats doing this on the interwebs and thought it looked funny. Either way, if it's sight related try getting him checked out; if it's not, he'll learn eventually.
Incidentally, if you do get him checked out for eye problems and he needs glasses, I'd like to recommend the Transitions lenses that they advertise on TV, especially if you're in one of the Western states and/or he goes outside a lot. My primary pair of glasses have Transitions in them, they work really well commuting back and forth from college because of all the sunlight we get in Wyoming. It'll help protect his eyes without him having to keep up with another pair of sunglasses (it's all I can do to keep up with my one pair that I wear all the time.)
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"Yeah, so this one time, I tried playing poker with tarot cards... got a full house, and about four people died." ~ Unknown comedian
Happy New Year from WP's resident fortune-teller! May the cards be ever in your favor.