Happiness to Hostility

Starting with Happy and then searching for synonyms, it took me 16 words to get to Hostility.

Happiness = Contentment = Comfort = Ease = Quiet = Calm = Untroubled = Blase = Uninterested = Apathetic = Emotionless = Cool = Standoffish = Unapproachable = Unfriendly = Hostility

Fun With My Thesaurus

It takes just 16 words to go from Intelligent to Ignorant (though I've seen many people take less).

Intelligent = Clever = Resourceful = Creative = Original = Authentic = Genuine = True = Unvarnished = Straightforward = Uncomplicated = Simple = Elementary = Rudimentary = Unsophisticated = Ignorant