Two for "Best": Little Bird by Annie Lennox. Not only did being preganant not stop Annie from turning in a fun performance herself channeling her inner Liza Minelli but also featured eight Annie impersonators each adopting a different look from one of her videos (some male, some female) most of whom look pretty darn close (My vote for "winner" goes to Beethoven Housewife Annie)
"I Don't Care" by Shakespear's Sister. This was the video that had the unenviable task of following the classic "Stay" video. But it didn't disappoint. Not only was it lots of campy fun but also was very eerily prophetic in displaying what would later become a rather accurate representation of the rift between Siobhan and Marcella.
Two for worst: "If I Could Turn Back Time" by Cher. Cher dearie, Rule #1 of making a music video is to remember to put on your pants before filming. Rule #2: If you manage to forget Rule #1, make sure the title of the video isn't "If I Could Turn Back Time" or you're just opening yourself up to way too many obvious jokes.
"True Blue" by Madonna. No, not the real video - that was wonderful. But the American MTV had a "Make My Video" contest where they had viewers make their own video for True Blue. Not only was the winning video pretty bad but it also meant that it would be the one played on MTV and anyone who wanted to see the real far superior video had to tune in to a rival video show like Friday Night Videos or Night Tracks.
One for Funniest: "The Homecoming Queen's Got a Gun" by Julie Brown. Exhibit A as to why she is one of the Coolest People in the Universe.
One for Craziest: The Beloved's "Your Love Takes Me Higher" remix. The band released a videotape compilation of the videos from their Happiness album. At the very end of it, an uncredited on the package video comes up which is a remix dub version of Your Love Takes Me Higher with the visual being a soft porn video of Jon Marsh and his then girlfriend!