Nanny Dickering is Cracked's principal interviewer and one of the publication's regular cast of characters. She is, perhaps, the character most heavily identified with the magazine after mascot Sylvester P. Smythe and made over a hundred appearances over the years.

Although her appearance varied throughout Cracked's history, Nanny is typically portrayed as a tall, leggy blonde with a beehive hairdo. When appearing in color, she is usually shown to be a standard blonde, but has been shown as platinum blonde as well. Her eyes have been depicted as either blue or green. Although she dresses appropriately for her circumstances, her clothes are generally tight fitting, designed to show off her ample figure. She often wears a bow or a headband in her hair and high heels. Despite her obvious sex appeal, she is usually portrayed as being good-natured and relatively innocent.

Not super happy with how this turned out. Trained mostly on Bill Ward art. But other artists were used as well, but tried to keep it to the same look. Most of the art was black and white, but there were a few color pictures as well. I don't know if it's because of the mainly black and white comics used, or the art styles were too different, but overall it's hard to get her to look right. Works best when there's no quality tags or negative tags.