I've been thnking of ideas like this for a long time. Heck, back in 1999, I had an idea for a Toonheads-style Henson series, featuring themes involving the Muppets, Sesame Street, Fraggle Rock, the creature shop, and other stuff.
I was thinking that such a Sesame Street series should be a half-hour, but looking at my lists, including what skits should be included along with narraration (I didn't mention specific clips for montages, such as when a narrarator speaks), it seems like all of that wouldn't fit a half-hour, especially if there are plenty of complete sketches. Then again, Toonheads occassionally had hour-long specials, and I don't see anything wrong with follow-ups to certain episodes so that more can be included.
But here is more content for certain "episodes".
episode 9. animation
*a brief introduction talking about how the show has always featured animation
*information about Bud Luckey, including three of his complete sketches: Two-Toucan Two-Steps, The Alligator King, and That's About the Size of It
*information about Cliff Roberts, and four complete sketches, including one Jasper and Julius sketch
*information about Sally Crushnik, including three complete sketches
*information about Mo Williems, including three complete sketches, such as Suzie Kabloozie singing Every Kitty Sleeps
*information about Tee Collins, including three complete sketches: Wanda the Witch, Nancy the Nanny Goat, and X-xylophone (his only three sketches mentioned in his Muppet Wiki page)
*information on Bruce Canyard, including three complete sketches: The Nobel Ostrich, If You've Lost Your L, and something else
*information about classic cartoon characters making occassional appearances, with three complete sketches: The Pink Panther and K, Batman crosses the street, and Superman talks about the letter D
*a few additional segments: Pinball Number Count #2, Typewriter: A-airplane, and Lillian, Big Sister
episode 11. Kermit the Frog
*information about Kermit's beginnings on Sam and Friends, and info about him being one of the worlds most famous Muppets (hopefully Disney would allow for clips from the movies and The Muppet Show; heck, hopefully Disney would allow for a Kermit-themed show), and then talking about how Kermit has been featured alot on Sesame Street.
*Kermit's W Lecture (perhaps the screen can flip when part one ends and part two begins)
*Kermit and Professor Hastings talk about parts of the body
*information about Kermit's signature song, Bein' Green (with brief clips from all three versions)
*Bein' Green with Lena Horne and Kermit
*information about Kermit's team-ups with Grover
*Kermit and Grover demonstrate up and down
*Grover attempts to sell Kermit a nose warmer
*information about Kermit's job as a news reporter
*Sesame Street News: Pinnocchio
*This Frog
*Kermit and Elmo talk about hapy and sad
*Kermit has Cookie Monster test out a machine in order to get a cookie
*If I Were
*Kermit, Shola, and Fanny demonstrate "next to"
*Kermit and Grover demonstratelight and dark
*information about how Sesame Workshop now owns the Sesame Street Muppets, and how Disney owns Kermit, leading to a clip from Kermit's last Sesame Street appearance
*clip of Kermit and Al Roker reporting on the hurricane on Sesame Street
episode 12. Roosevelt Franklin
*information about how Roosevelt Franklin was created
*Roosevelt Franklin Counts
*Roosevelt Franklins Days of the Week
*Same Sound Brown
*information abotu Roosevelt Franklin Elementary School
*Roosevelt Franklin teaches his class to spell poision
*information about The Year of Roosevelt Franklin album
*Roosevelt Franklin teaches his class the importance of excercise
*the departue of Matt Robinson, and whetehr he continued to voice Roosevelt after he stopped playing Gordon (this should settle to us fans once and for all if somebody took over the role of Roosevelt)
*Roosevelt Franklin teaches his class traffic safety
*info about Roosevelt being taken off the show due to being seen a sa negative stereotype
*Roosevelt Franklin talks about famous black people in history
episode 19. parodies
*talk about how the show has had many parodies over the eyars. Perhaps each sketch could have an introduction, explaining the parodies, and maybe even showing clips or stils from the source material
*Miami Mice: The Count needs to be at the space station
*Monsterpeice Theater: Upstairs, Downstairs
*Extreme Makeover: Home Addition
*Don't Know Y
*Furry Happy Monsters
*U Really Got a Hold on Me
*What's My Part?: Foot
*The Add'Ems Family
*Ernie loves his boat
The Dr. Feel Show: Dr. Feel meets Dr. Phil
*Hey Food