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Well, i'd say get Gragas, Esq. NOW cause it's on sale and is awesome.
Make sure to pick up gentlemen cho'gath and corporate mundo, too. Funniest and best skins in the game IMO.
Get Pharaoh or Re-gifted amumu (Pharaoh looks like a little barrel ingame )
Nunu bot is pretty hilarious if you like him.
Traditional Lee Sin looks awesome ingame
Urf skin for Warwick - A MUST if you play warwick.
Lion Dance Kog'Maw has awesome effects.
Outback Renekton for lulz.
Brolaf because...he's a bro.
Either trundle skin for maximum trolling.
Karate Kennen looks casual and well designed if you look non "funny" skins.
Gangster Twitch is funny.
Groovy Zilean is awesome too.
anyways, these are the best skins in my opinion.