As part of a community relations effort by the hospital, Doogie is asked to go to the high school and teach sexual education. On his first day, he is challenged to an after school fight by the captain of the football team.
In return for saving the life of the coolest guy in school, Doogie is rewarded by being allowed to hang around with him and his cool friends. With his new found coolness, Doogie neglects Vinnie and disobeys his father.
When Doogie's dad begins to feel old and unimportant, he decides to quit his medical practice. Doogie and his mom then decide to gather many of the patients he has helped over the years in hopes of changing his mind.
When Doogie and Jack hear a rumor that they are neck and neck for Resident of the Year, they both try to gain an advantage by trying to influence the judges which ultimately puts them in awkward positions.
Doogie is surprised when Raymond, the former gang member who once held him hostage, shows up at the hospital. Impressed by Raymond's transformation into a responsible person, Doogie invites him to dinner and gets him a job at the hospital.
"Dr. Doogie" becomes an overnight sensation after he appears in public service announcements on a popular music channel. However, when his fame gets in the way of his job and normal life, he must choose whether he wants to keep up the hectic schedule.
While trying to talk his pregnant French teacher into helping him improve his failing grade, Vinnie ends up stuck in an elevator with her. She starts to go into labor and he is forced to call Doogie for help.
Doogie argues with his dad over whether he can buy a 1957 Chevy convertible. At the hospital, Doogie tries to get through to a mentally retarded patient who refuses treatment for a potentially fatal illness.
Doogie admits a homeless man to the hospital who turns out to be Blind Otis Lemon, a legendary blues player long thought to be dead. When Otis is scheduled for surgery to remove a tumor that could possibly leave him deaf, Vinnie and Raymond sneak him out of the hospital for one last gig.
One of the hospital benefactors, an elderly woman comes for her annual physical. Canfield informs Doogie that she's only generous unless she's told that something is wrong with her. So he tells Doogie to make something up.
Doogie is jealous when Wanda becomes friends with a male nude model in her art class. At the hospital, Doogie suspects that a pretty young model is bulimic. The hospital holds its annual bachelor auction with Doogie participating for the first time.
Vinnie is depressed when he learns that Janine's parents offered her a car if she would break up with him. Katherine's parents come to visit for Thanksgiving which causes tension with David who never felt they accepted him as their son-in-law.
Needing a recommendation to get into NYU film school, Vinnie poses as an orderly to try and meet the head of ABC television who is staying at the hospital. Meanwhile, Doogie's first poker night with the guys at the hospital is memorable for all the wrong reasons.
Doogie is attracted to a nursing student who he asks out behind Wanda's back. A man who is staying at the hospital is married to two different women without each one knowing about the other. He asks Doogie to try and prevent each one from seeing the other.