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The evolution of Oscar the Grouch.

Image As seen in / Year Notes
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Sesame Street
Season 1
(1969)
The original Oscar puppet is orange. This version used in the early episodes of season 1 is built around a right-handed work glove, with no foam interior. At this time, the way the set is built forces performer Caroll Spinney to use his left hand, making this version of the puppet look awkward. This puppet's eyes can shift left to right. The puppet has a visible arm in episodes 9 and 10, and briefly appearing in episode 4 (all taped prior to the first episode).
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Sesame Street
Season 1
(1969-1970)
This rebuilt Oscar, used for the remainder of season 1, has a larger foam head and an eyebrow mechanism. The set was changed to allow Spinney to work with his right hand.
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The Flip Wilson Show
Episode #1 & #5
(mid-1970)
Between the first and second seasons of Sesame Street, Oscar appeared on The Flip Wilson Show with a new design including green fur and a blue eyebrow. His head had yet to take its final shape. An altered version of this puppet would be used for Granny Grouch in the second season premiere, and Matilda in episode 0372.
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Sesame Street
(late 1970-1986)
For the second season, Oscar's eyebrow has reverted back to brown and his head has been remodeled into its final shape. Although the puppet would be refurbished occasionally during this time, the design stayed consistent. In The Wisdom of Big Bird, Spinney said that the current Oscar's eyebrow (as of the time the book was written) is still the same piece of fur used for the original orange Oscar puppet.
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Sesame Street
Season 2
(1970-1971)
This Oscar puppet can be seen in the 2-part sketch in which Ernie loses his Rubber Duckie, as well as in several closing signs.
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Sesame Street
Episode 0573
(ca. early - mid 1970s)
This rarely seen Oscar variant has a slightly smaller head, a big lower jaw, and eyes that are further apart.

Another defining feature is that not only is his eyebrow mobile, but his eyes are as well (much like the first puppet).

This particular Oscar puppet can be spotted in the background during "C is for Cookie" and in The Sesame Street 1974 Activity Calendar, and was also used in the "Rainbow Connection" finale in The Muppet Movie.[1]

During the 1970s and 1980s, the puppet would be recycled for other Grouches, such as Hermine, and Oscar's grandpa and his brother, Ernest.

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Sesame Street
(1986-2012)
Oscar's fur becomes matted over time, which makes it appear shorter and less messy.
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Sesame Street
Season 25
(1990s)
An alternate puppet used during the mid-1990s and was later used by Caroll Spinney in live appearances along with some episodes (including 4173, 4236, and The Word of the Day segments with Nicole Kidman and Maria Menounos).
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Sesame Street
Season 44
(2012-present)
Oscar is refurbished with darker green fur and a solid pink tongue.
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Sesame Studios promo (2016-present) Another Oscar puppet that had been used for live appearances is used more regularly as a spare puppet starting with season 46. This puppet has shaggier fur, bushier eyebrows and the left side of his jaw is angled and crooked. The puppet is reworked with a fuller, rounder head by season 49, as seen in Episode 4912.
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Caring for Each Other (2019-present) A new Oscar is built with a more circular head and longer, shaggier fur. This variant first appeared in A Swingin' Sesame Street Celebration. During season 51, shades of brown were mixed into Oscar's fur.
Planning
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Design sketches for Sesame Street
(1969)
Jim Henson had initially intended Oscar to be magenta, as opposed to orange. The reason for the color change was because at the time, television cameras couldn’t process magenta shades well. In these early sketches, Henson experimented with how the puppet would move, appearing slyer and more sinister than the grouch he would become.

Sources

  1. ↑ The Art of The Muppets Still of the "Rainbow Connection" finale, shot from a different angle