Sesame Street Unpaved is a documentary that originally aired on TV Land in 1999. 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 in the framing footage as well.
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
- King of 8
- 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 episode 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 winning clip was "Rubber Duckie."