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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.

Segments

Picture Segment / First Appearance Description
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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.
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Mud
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."
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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.
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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."
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Addition
Episode 1599
Telly tries to postpone today's show, but Oscar, overcome with the Grouch Flu, gleefully agrees to participate. Mindie Grouch of Elcart, Indiana asks about addition and Oscar demonstrates using pretty flowers. He realizes what he's doing and asks Telly to end the show hastily.
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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.
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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.
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Listening
Episode 1880
Telly reads a letter asking about the importance of listening. Oscar drives Telly crazy by blatantly paying little attention to everything he says, forcing Telly to repeat the details over and over. Oscar finally concludes that while listening is a good way to learn what people have to say, not listening allows one to have some fun watching the speaker get angry.
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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.
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Quiet and Loud
Episode 1928
Telly reads a question regarding the difference between quiet and loud. Oscar talks quietly to Telly, then shows off a pile of junk, which when tipped over, will cause it to fall. Telly loudly tells Oscar not to, showing loud. Oscar tips it over anyway for fun.
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Games
Episode 1938
Telly introduces a computerized edition of Ask Oscar, where the computer will give programmed answers to today's questions. Telly is relieved at this change, believing the computer will be much more reliable than Oscar. Telly reads a question about games to play at Grouch birthday parties. He commands an answer on the keyboard and the screen gives Oscar's response - "NO Heh Heh Heh!!"
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No
Episode 2043
Telly reads a letter with lots of "yes or no" questions. Oscar answers each one with "no," using a sign to answer it. The final question is an offer of old shoes, which Oscar realizes he's turned down by always answering "no."
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The Letter X
Episode 2049
Telly reads a viewer question regarding which letter Grouches like the best - G or O. Oscar's answer is that X is the best letter, as it can be used to cross out things they don't like. He demonstrates by sticking an X on Telly's face.
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Practice
Episode 2135
Telly reads a fan question asking how they can become as grouchy as Oscar. He tells the viewer that practice is the key. Telly thinks Oscar's response will make the viewer very happy, a nice gesture Oscar doesn't seem pleased with doing. Telly suggests Oscar needs to practice being grouchy as well.
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Discussions
Episode 2163
Telly gets a letter asking if Grouches like to have discussions. However, Oscar won't come out of his trash can, and refuses to discuss the question.
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Imagining
Episode 2193
Telly reads a letter from Barbie Dull, who asks what Grouches like to imagine. Oscar says he never learned how to imagine, so Telly answers for him, closing his eyes and imagining pleasant settings, while Oscar rebuts with more grouchy settings.
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Shapes
Episode 2265
Telly reads a letter from Robin Sunshine of Happyville, Montana. Oscar is repulsed by this information, but intrigued by their question - "Why are you such a crabby old Grouch?" Oscar fumbles coming up with an answer, but then produces a triangle and a square. He gives his answer - "Why is a triangle a triangle? Because it's a triangle. Why is a square a square? Because it's a square. And I'm a grouch because I'm a grouch." Telly doesn't accept this and points out the geometric reasoning behind the names.
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Linda Substitutes
Episode 2316
A grumpy Linda substitutes for Oscar.
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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.
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SH
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.
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Silly Answers
Episode 2465
Oscar is once again stubborn to answering any fan questions. Telly reads one anyhow from Mrs. Grimble Grouch of Kitty Litter, North Carolina - "What makes you think anyone should listen to your silly answers anyway?" Oscar is insulted by such a silly question and refuses to give her the satisfaction of an answer. Telly doesn't find the question silly and asks why Oscar even runs this show if he feels he shouldn't be listened to in the first place. Oscar thinks and concludes that the Grouch audience needs to listen to his show, otherwise they can't judge whether his answers are silly or not.
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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).
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NO
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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Annoying Your Neighbors
Episode 2808
Telly reads a question from Guy Smelly, asking how to annoy his neighbors. Oscar demonstrates bothering Gordon and Susan by banging a wooden spoon on his can. His next question asks about how sound is produced. Oscar prepares to demonstrate with his spoon again, but Telly suggests something else. Oscar goes into his can to find an alternative method.
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