I'm looking for the name of a Special that aired around Christmas on the USA Network I believe. I believe i was an early teenager so it woulda been anywhere from 92-95. I believe the only real thing Christmasy about the whole show was the ending song where they wrapped about Rudolph & Santa Claus' the show is kind of hazy but I remember that atleast, I also think I remember the opening segment taking place in a Diner at night? Can anyone help me out?

You must be thinking of the TV special "The Chipmunks: Rockin' Through the
Decades" (but it was on one of the major broadcast networks). A retrospective of the characters that first burst on the scene in 1958 as
David Seville & the Chipmunks, the show was hosted by Will Smith and
featured guest stars Little Richard, Kenny Loggins, Ben Vereen, Shelley
Duvall, Raven-Symone, Richard Moll, Markie Post and Michael Jackson. The
show had a holiday flavor and also included clips from THE ED SULLIVAN SHOW
(in which the recording artists were first seen as hand puppets), THE ALVIN
SHOW (1961; their animated debut) and new footage. Produced by Ross
Bagdasarian Jr. (son of the creator of Alvin, Simon & Theodore). It was
released on video cassette many years ago. I taped it when it first aired.