LittleJerry92
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To put it simple.Something still isn’t right though.
The insert of Ray and Elmo has the former wearing a black coat and red shirt, which appeared as early as season 27. The alphabet song has him wearing the same clothing.
The "Two Princes" song has Chris wearing a purple shirt. In the alphabet song, he's wearing the same shirt. The two Princes song debuted in season 27, indicating that the Ray and Elmo insert actually did debut in season 27 because, as I previously mentioned, Ray and Chris are both wearing the same clothing in both the alphabet song and their individual inserts that I mentioned.
Tony Bennett is wearing a tan jacket in that song, as well as his individual insert when he sings "Little Things" which also debuted in season 27.
Mikaela, I'm gonna give you some helpful advice. When a segment is listed as "earliest known appearance", that doesn't necessarily mean it's the first. There are some skits that do say first, but that's listed when it's officially known to be the first debut. If you're trying to figure out when a certain skit debuted, it helps to pay attention to the Anything Muppets that appear, how the main characters look in terms of puppet design, and what the human cast members/guest stars are wearing if the latter ones appeared in other inserts.