The series depicts the tribulations of the title character Parker Lewis, a Santo Domingo High School student, for whom nothing is impossible. Parker often narrates in shows. Just like his best friends, Jerry Steiner and Mikey Randall and his girlfriend Annie Sloan, his prime concern is achieving and maintaining "coolness" during the turbulent years of puberty. However, their efforts are often thwarted by Parker's little sister, Shelly, and principal Grace Musso. Apart from various aspects of teenage life, embedded in a surreal, living-cartoon-like quality and the clever camera angles and filming techniques (dissolves from one scene to the next were done by ever larger pixels), an episode regularly contains more or less subtle references to movies, politics, and celebrities. The 3,100 students are called "Flamingos", after their football team.
Jerry gets move into the A.S.A.P. program which makes him a senior, when he gets a B+ on his first test he freaks out, drops out and starts laying bricks. Grace has a recurring dream about The Scarlet Letter.
Parker and Mikey help Jerry overcome stage fright so he can win the district science fair.
At the mall, Parker searches for his elusive dream girl, Jerry searches for a job, and Musso tries to stop spending money.
While Annie is away, Parker and Mikey go on a double date with two girls that they meet.
The buds use the school's pirate radio station to unwittingly turn everyone against them.
Jerry gets Kubiac elected homecoming king as a joke, but Larry takes it seriously.
Parker's first bad day of the year is the last day of the school year.
Parker's mother plays Cupid for Ms. Musso and her brother. Musso changes her approach and thinks she has a relationship that will last.
Larry is hired to prevent shoplifting at the Lewis's video store, but he scares away the customers.
Parker asks out a girl he met on a computer bulletin board, but considers backing out when she is less than he hoped for.
Nick is where Parker turns to for advice when Annie breaks his heart.
The buds try to break Jerry of his lack of self-confidence when he is without his coat.
Parker's favorite teacher must leave teaching for a better paying job to support his family.
Parker and Mikey invite Jerry to Mikey's apartment for a weekend of being men, they later decide a trip to a strip joint is in order. Jerry is out of the room when Parker and Mikey get pulled out of there in a raid. Jerry experiences this part of life on his own. Musso battles her fear of spiders by enlisting the aide of Kohler, who is only to happy to help.
Parker must double-date with Shelley on Prom night, when his parents decide Shelley is a little young to be attending. At the event Shelley turns up missing just as his parents arrive.
Mikey has a problem with writer's block which may cause him to attend summer school. Everyone gives him help by pitching story ideas, one of which takes on the style of the old Parker Lewis Can't Lose.
After being left out of everything, Jerry goes on a quest to become cool.
In a remake of the film Cape Fear, tough guy Brad Penny saves Parker's life and tries to befriend him. Parker becomes suspicious and vows to never let Brad get to him.
Mikey needs extra cash so he gets a job at the diner.
Musso wants the buds to make a documentary about the school, but Parker has no time thanks to his new history teacher.
Shelly tries everything to meet her favorite rock star.
Musso mellows as she approaches her 40th birthday, so Parker calls in Dr. Pankow to get the old Musso back.
Parker has a crush on one of his teachers. Jerry wants a part in the school's production of The Music Man.
A local business man sponsors a family build-a-better-toaster contest and Mikey can't participate because his mother doesn't have the time.
Shelly blackmails Parker into helping her find a date for a party.
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