It was hosted by Sonia Manzano, joined by Caroll Spinney, Martin P. Robinson, Bob McGrath and Loretta Long in a series of conversations on the Sesame Street set which frames itself around a number of classic clips. Many of the clips shown had their titles and original air dates listed on-screen as well. Oscar the Grouch makes a cameo at the end of the special.
The following segments were shown in a more featured capacity than those shown in a clip montage...
- The Sesame Street Unpaved opening, followed by an "in color" identification, the animated episode number sequence for the first episode, and a montage of various openings, with on-screen text referring to the openings as from 1969, 1979, 1989 (though the opening introduced in 1992 is shown instead), and 1999.
- Gordon shows Sally around Sesame Street
- Clips from the Sesame Street Pitch Reel, including the boardroom coming up with names for the show and Kermit coming up with Sesame Street for a title
- "Bein' Green" (original version)
- "Rubber Duckie" (second version)
- Kermit and Joey sing the alphabet
- "Pinball Number Count" #12
- Let's Sing a Song of Three
- The King of Eight
- Rollercoaster 123
- "Jazz #10"
- Mad Painter
- Roosevelt Franklin talks to his mother about how at one time he could not spell
- Big Bird learns about Mr. Hooper's death.
- The adults see Mr. Snuffleupagus for the first time.
- "Ladybugs' Picnic"
- "C is for Cookie" (original version)
- "What's the Name of That Song?" (original version)
- Bob and Luis sing "Sing" (during the end credits)
- Shortly before this special aired, Noggin's website put up four clips for fans to vote on, and the winning clip was shown after this special aired. The nominated clips were:
- The documentary claims that "Pinball Number Count" first appeared in Episode 0989, when in fact, "Pinball #3" first aired in Episode 0978.
- Written and Produced by Josh Selig
- Directed by Ken Diego
- Associate Director: Tim Carter
- Cameras: Frank Biondo, Juan Barrera, Ron Washburn, Hugh Walsh, James Miller
- Muppets, props and costumes provided by The Jim Henson Company Workshop
- Special Thanks: Alice Cahn, Arlene Sherman, Lori Sheer, Cheryl Henson, and the cast and crew of Sesame Street