Cranky is a grumpy donkey, who travels Equestria in search of Matilda, and comes to Ponyville in "A Friend In Deed" (season 2) To settle down. When he arrives, Pinkie tries desperately to make friends with him, even replacing his wig when she accidently destroys it. She only makes friends with him when she reunites him with Matilda, his "special friend".

Later, as part of the 100th episode celebration, the two donkey's marry. Although a misprint meant that they had to move their wedding to a day earlier, they were still able to pull it off with the help of the ponies in the town (Even if there was a bug bear attack going on at the time)

While searching Equestria, he made good friends with Steven Magnet. And although they had good times together, the one thing he was always set on was finding Matilda.

He wears a black, dirty wig, which is replaced later on in the episode by a larger, golden wig.