Chip and Dale are major antagonists in Donald Duck franchise.
Chip is the brains of the duo and thus is shown to be clever, fearless, and somewhat bossy. Unlike his best friend, he's a quick thinker. When dealing with Donald, Chip shows to be much more of a threat than Dale, both mentally and physically. He is also no-nonsense and becomes easily frustrated with Dale's incompetence.
Dale is sometimes lazy, dim-witted, and clumsy, and can be a little more emotionally sensitive. In earlier appearances, he was completely foolish to the point where he can truly be called an idiot. In later years, that aspect of his personality was toned down to just being nervous, timid, wisecracking, laid-back, and reluctant.
While the two are nearly inseparable and count each other as their closest friends, the one thing that can tear them apart is a romantic interest. They have been known to have feelings for the same girl most of the time and battle each other for the affections of the girl in question.
They sadistically tormented Donald Duck in several cartoons.
They sadistically tormented Pluto in several cartoons.
They sadistically tormented Mickey and Pluto in Squatter's Rights (1946). They even burnt Mickey's shoe and framed Pluto for it.
They stole Donald's pancakes in Three for Breakfast (1948).
They tried and stole Donald's Nut Butter in All in a Nutshell (1949).
They antagonized Donald when he was riding his penny-farthing to Daisy's house for his date in Crazy Over Daisy (1950).
They stole Donald's crop of apples in Donald Applecore (1952).
They tried to steal Dolores' peanuts in Working for Peanuts (1953).
They tried to steal Donald's acorns in Donald and the Big Nut (1999).
They tried to stop Mickey from getting the last bag of nuts from a store after he eats them all in Mickey's Mixed Nuts (2000).
They stole nuts from everyone in the House of Mouse and frame Donald for it in the House of Mouse episode Chip 'n' Dale (2003).