Honorable mention: "UHF" -- The title song from his 1989 film UHF, released July 21st, 1989, the same weekend as When Harry Met Sally. Rick and Aaron are still fans of the movie ("It still holds up," Rick said).
5. "Dare to be Stupid" (also used in 1986's The Transformers Movie!) -- a style parody of Devo, whose sound the members of Devo said he nailed.
4. "Christmas at Ground Zero" -- Remember who was in the video? You might be surprised. (And a lot of it's made up of mid-century footage of both Christmas shopping and nuclear explosions...)
3. "You Don't Love Me Anymore" -- People thought Weird Al had done a parody of the Extreme song "More Than Words." He hadn't, but he decided to do the video in the style of Extreme's video.
2. "Bob" -- his style parody of Dylan. Even the title is part of the joke.
1. "One More Minute" -- Weird Al wanted to do a duet version of this with Frank Sinatra! Didn't happen. Darn.
Trivia that came up while Duran presented the list: Aaron thinks Weird Al has had the same backing band since the start of his career; so they'd be one of the longest-lived bands in America.
This was fun. I should do my own list.