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
In and On
Episode 1493
In the premiere segment, Telly reads a letter from Yucchina Blechman of Sandusty, Ohio, who wishes to know about on and in. Oscar thinks Telly should help with the demonstration. He produces a box, which he puts on his head, then has Telly put his head in the box. He repeats this using a bucket, to Telly's chagrin. Telly wishes to switch roles in the proceedings. Oscar puts some ripped-up newspaper in a box, then throws the pieces on Telly.
1505 02
Episode 1505
Telly reads a letter from Matilda Yucchman of Chagrin Falls, whose Aunt Alice gifted her a "UD" and she doesn't know what to do with it. Oscar has also been given the same thing and shows how to make it into the word "MUD."
The Count Co-Hosts
Episode 1573
The Count fills in for Telly, but gets carried away in counting questions and reads more letters before Oscar can give a full answer to any of them.
About Love
Episode 1595
In a two-part segment, Telly stops the show, knowing full well that Oscar isn't going to cooperate and come out of his can on cue. Oscar, however, keeps his promise and comes out, but goes back inside before Telly can present the question. Learning that the question is from Grundgetta, asking about love, Oscar answers by singing "Love in the Junkyard."
Longest Grouch Word
Episode 1829
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.
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.
Linda Substitutes
Episode 2316
A grumpy Linda substitutes for Oscar.
The Count Co-Hosts Again
Episode 2359
The Count fills in for Telly, who's at the dentist. Oscar, however, is not up to answering any questions today. The Count proceeds to read a letter, asking how many ways there are of getting rid of somebody. Oscar inadvertently provides an answer as he keeps telling the Count to beat it.
Episode 2431
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 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 2605
Telly starts up another episode of "Ask Oscar," but Oscar has little interest in answering any questions. He hangs a sign reading "NO" from his can, which Telly uses to answer the latest question. However, because of the wording of one particular question, Oscar winds up with a potential visit from the writer.
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