Dr. Pickell is the school counselor at Wayside School. He only appears in Wayside School Gets a Little Stranger, in which two chapters focus on him. He uses hypnosis to help children with their problems, but often he also throws in a smaller joke, which causes new problems. Originally, he worked as a psychiatrist, but he was fired when people caught onto his jokes. Afterwards, he got a new job as a counselor, in which he kept doing the same.
It is described that Dr. Pickell has a scary face, with big, bushy eyebrows and a small beard on his chin. He wears small glasses as well. Often, he uses a pickle-shaped stone to hypnotize people, getting rid of one bad habit in exchange for a new one.
Although Dr. Pickell does work efficiently with his job, often, he does like pulling jokes as well. This leads to undesirable outcomes, such as one person who ended up slapping their husband whenever they said "potato" and one person who quacked like a duck whenever they saw a freight train with over 20 cars. While people are usually scared of him at first, they often end up calm after seeing him, suggesting he also calms them down using hypnosis.
"Dr. Pickle" in Wayside School Gets a Little Stranger introduces this character, showing his results with a woman who wanted to stop smoking, only to start slapping her husband whenever he would say "potato". It also reveals the side-effects of a few others, which lead to him losing his job and becoming a school counselor.