Ask Oscar is a recurring series of Sesame Street sketches, first appearing in season 12 (Episode 1493). Each segment was introduced by Telly Monster, and they involved Oscar the Grouch answering mail from viewers.

This sketch was also revived as the main street story in Episode 4118.


Picture Segment / EKA Description
Planning for Vacation
Episode 1845
Bob fills in for Telly as Oscar shows how he would plan for a vacation. Oscar packs a suitcase, roughly exactly as Bob would, but when Bob lifts the suitcase, everything falls out though a torn side.
V Word
Episode 1917
Oscar gets a letter from a viewer who wants Oscar to talk about a V word. Oscar talks about the V word "Vibrate". Telly doesn't know what "vibrate" means, so Oscar has Telly hit a steel V that Oscar has with a hammer, which gives them both a vibrating feeling.
Episode 2163
Telly gets a letter asking if Grouches like to have discussions. Howver, Oscar won't come out of his trash can, and refuses to discuss the question.
Longest Grouch Word
Episode 2275
Linda's friend Timi assists Oscar, translating Oscar's words in sign language. Oscar answers a letter from someone who wants to know what the longest Grouch word he knows is. Oscar states that the word is "supercalifragilistic-yucka-alidocious" (a reference to "Mary Poppins"), which is hard to sign, especially when Oscar repeats it many times.
Linda Substitutes
Episode 2401
A grumpy Linda substitutes for Oscar.
The Letter X
Episode 2573
Oscar is asked what the letter X is good for. Oscar shows that the letter X can be used to cross out his daily annoyances, such as bothersome neighbors, annoying letters and annoying letter readers (Telly).
Episode 2678
Telly reads a question from a Grouch who wishes to know what sound the letters "SH" make. Oscar makes the "Shhhhh" sound, but Telly thinks he's shushing him.
The Count Fills In Telly is on vacation, so Count von Count fills in for him. Unfortunately, the Count (being the Count) has too much fun counting the questions mailed in by viewers; he doesn't give Oscar the chance to answer one before moving along to the next! When the Count gets up to six, an exasperated Oscar hollers at him, "Will you stop counting the questions!!?" The Count's reply: "Ah, that makes seven. Seven questions! Ha ha ha!!" As thunder and lightning flashes, Oscar sighs, "Can you believe this!?" That, of course, makes eight questions...