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'Pee-wee Herman, comedian Paul Reubens' signature character, is the titular protagonist of Pee-wee's Playhouse. He is the owner of the playhouse. He is a zany, childlike fellow with a pomaded crew-cut, a too-small gray suit, a bow-tie, a high, nasal voice, and a frenzied manner. His playhouse boasts oddball characters and talking furniture and he likes to ride his bike and cook, whipping up such delights as Ice Cream Soup.
He actually has objected to the Secret Word gag twice, both times harshly demanding silence from the Playhouse's denizens. He also can be quite stern and serious when he needs to be, as seen in The Gang's All Here.
Some fans have suggested that Pee-wee may be suffering from Peter Pan syndrome or insanity.
His zany antics, in the first season, angered characters such as Mrs. Steve and Captain Carl. When Role Playing with his friends, he acts like a tyrannical monster, looking down on his friends as slaves that he rules over with an iron fist.
In 1977, The Groundlings staged a performance in which its members created characters one might see in a comedy club. Reubens decided to play a guy that everyone immediately knew would never make it as a comic, partly because Reubens couldn't remember jokes in real life – he had trouble remembering punch lines and couldn't properly piece information in sequential order. Pee-wee Herman was born that night, his distinctive guttural, "Ha Ha," followed by a low, "Heh Heh Heh," laugh became the character's catch phrase, as did his insult comeback, "I know you are, but what am I?" (Original use of this quote, however, dates back at least to the 1970s, as reported in Lee Thayer, Communication (1974), page 21).
Pee-wee Herman's signature gray glen plaid suit (which he affectionately refers to as a "Pee-Wee suit" in Playhouse) was originally a custom-made suit that Reubens had borrowed from the Groundlings director Gary Austin; the small red bow tie was given to him by an acquaintance. Pee-wee's later checkered clothing and persona were largely lifted from manic 1950s children's TV host Pinky Lee. Also incorporated into the look were short black hair, pale skin with red rouge and red lipstick (dropped in the subsequent Playhouse seasons).
Pee-wee is commonly portrayed as an impatient and fun-loving child with dainty, effeminate mannerisms and quirky facial expressions. His age has never been explicitly stated; although, he once proclaimed on The Pee-wee Herman Show, "I'm the luckiest boy in the world". David Letterman once said of the character, "What makes me laugh ... is that it has the external structure of a bratty little precocious kid, but you know it's being controlled by the incubus – the manifestation of evil itself". While the character is typically cheerful and flamboyant, Pee-wee has indeed displayed an aggressive side, including his vicious pool battle with Francis in Pee-wee's Big Adventure. He also played vengeful tricks in the aforementioned film and occasionally threw childish tantrums on Pee-wee's Playhouse. Reubens has said that he feels Pee-wee "resets" after each adventure, his experiences only changing him slightly, and compared him to Dorothy Gale at the end of The Wizard of Oz. In the episode Chairry-Tee Drive, Pee-Wee flashes back to when he was a young boy (9 to 10 years old) while holding one of his old suits, suggesting that Pee-Wee's current physical age was around his early 30s while his mental and emotional age is around age 10 to age 13. This is mentioned once by Pee-Wee Herman himself in Now You See Me, Now You Don't during Knucklehead's botched joke and again by Miss Yvonne in Heat Wave, with a flashback to Herman's childhood occurring in Chairry-Tee Drive. (Dr. Pee Wee and the Del Rubios reveals that the reason why he is nicknamed Pee-Wee is because of his suit being called a "pee-wee suit". This is mentioned again in Chairry-Tee Drive.)
In Pee-wee's Big Adventure, Pee-wee's Big Holiday and Pee-wee's Playhouse, the character surrounds himself with strange inventions and decorations and has no confirmed means of economic support, whereas Big Top Pee-wee depicts him as a farmer/inventor. During a June 1984 segment on Late Night with David Letterman, Pee-wee claimed he has a sister named Hermione who was a Girl Scout, his mother's name is Honny Herman, and his father's name is Herman Herman. He went on to say that everyone in his family has a first name that begins with an "H" except for him. This was again stated during a 1988 special which elaborated that Pee-wee was raised in Florida. However, in an episode of The Joan Rivers Show in which he guest hosted, he says that his parents' real names are Milton and Judy. However, in the fanfiction Conky's Newest Feat, Pee-wee's real name is given as Herman Reubens and he makes no mention of siblings. 
Pee-wee is a man with white skin and black hair (gray in current times). He wears a gray blazer and pants, a white button-down shirt, a red bow tie, and white sneakers.
- Pee-wee makes a cameo in Michael Jackson's Moonwalker as one of the disguises Michael wears.
- It is implied in the episodes Dr. Pee Wee and the Del Rubios and Chairry-Tee Drive that Pee-Wee is really a nickname inspired by his now-iconic gray suit, which he affectionately calls a "pee-wee suit" in both episodes. In the fanfics Everything's Super and Conky's Newest Feat, he states that it is indeed a nickname and that his real name is Herman Reubens.
- Pee-wee also makes an appearance in Back to the Beach where he performs "Surfn Bird" by the Trashmen.
- Matchbox, a toy company that made toys of Pee-wee and the gang, had made a talking Pee-wee doll and they had made a talking Freddy Krueger doll. Both dolls were made in the same factory which resulted in the voice boxes of the dolls at the time being swapped so that mean't there were Freddy Krueger dolls that said Pee-wee Herman quotes.
- Paul Reubens got the name "Pee-wee" from a toy harmonica he had when he was a kid. The name "Herman" was inspired by the last name of a kid Paul knew in his younger years.
- After Paul Reubens' arrest in 1991 Matchbox recalled all their toys of Pee-wee Herman.
- Pee-wee was inspired by "Pinky Lee", a character from a children's show in the 1950s who dressed and acted similar to Pee-wee.