The BEST episodes of Sesame Street season 21

Every episode of Sesame Street season 21, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Sesame Street season 21!

On a special inner city street, the inhabitants, human and muppet, teach preschool subjects with comedy, cartoons, games, and songs.

Last Updated: 3/3/2025Network: MaxStatus: Continuing
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#1 - Sleepytime on Sesame Street

Season 21 - Episode 4 - Aired 11/16/1989

Episode 2621
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#2 - Episode 2621

Season 21 - Episode 6 - Aired 11/20/1989

A baby book for Alice

Episode 2622
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#3 - Episode 2622

Season 21 - Episode 7 - Aired 11/21/1989

Shelley is afraid of Barkley

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#4 - Episode 2616

Season 21 - Episode 1 - Aired 11/13/1989

Episode 2675
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#5 - Episode 2675

Season 21 - Episode 59 - Aired 2/2/1990

Big Bird and Snuffy play games and Elmo sleeps over (repeat from Season 19).

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#6 - Grouchytown

Season 21 - Episode 33 - Aired 12/27/1989

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#7 - Episode 2727 - A day at the library

Season 21 - Episode 112 - Aired 4/17/1990

Bob finishes conducting his music students through the Sesame Street theme song. Big Bird approaches Bob with a counting song he just made up, which he hopes the kids can play. Bob gives him the baton and he conducts the kids through the song, which is "Old MacDonald" with the lyrics mostly replaced by numbers. The song stops at 40, since that's as far as Big Bird can count.

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#8 - Episode 2730 - Oscar writes to Grundgetta

Season 21 - Episode 115 - Aired 4/20/1990

SCENE 1 After welcoming the viewer, Gina sees Oscar writing something and wants to know what it is, but he tells her to stay away from his trash can. She tries leaning against it to get a view and he finally relents. He explains that Grundgetta is visiting her aunt in Trashylvania and he's writing a letter about all the rotten things she might be missing. Gina assures him that nothing rotten has happened, or will. Oscar continues writing anyway, detailing how Gina just ruined her shirt by leaning against his newly-greased can.

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#9 - Episode 2733 - Taking a trip to Africa

Season 21 - Episode 116 - Aired 4/25/1990

Big Bird and Snuffy imagine they're on a trip somewhere very different from Sesame Street. They picture themselves on an island in the middle of the ocean, but don't have much to do as they didn't imagine a pail and shovel. After their fantasy, the two enjoy the idea of visiting someplace new so much that they decide to take a real trip. Remembering what happened during their imagining, they begin to start planning ahead.

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#10 - Episode 2735 - Oscar tries proving Gabi is a grouch

Season 21 - Episode 120 - Aired 4/27/1990

Oscar and the Grouchketeers want Gabi to join their organization. He gives the kids a demonstration of "loud" and "quiet" and is pleased with Gabi, who doesn't follow any of Oscar's orders. He believes she's becoming more like a Grouch with each passing day, though Maria counters otherwise. He tells the viewer to stick around and see the other Grouch tests he'll be trying on Gabi.

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#11 - Episode 2736 - What will Gina do when she graduates high school?

Season 21 - Episode 121 - Aired 4/30/1990

Big Bird heads to sleep, while Hoots the Owl starts his day. They sing about their different sleep schedules. (First: Episode 2020)

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#12 - Episode 2740 - Another day in the library

Season 21 - Episode 125 - Aired 5/4/1990

Gordon makes his way to the library as he sings about it. Once there, he's joined by Susan, Linda, Elmo, Gladys the Cow and others.