In terms of movies:

Death to Smoochy: bad but entertaining. One of two Robin Williams movies where his character is so obnoxious that I cheer when he gets punched out. The secret is most of the main characters are loveable, even the Ma Barker style Irish gangster. Do childrens shows really have all these sleeze going on behind the scenes?

The Haunted Lantern: despite some gore this movie includes some of my favorite imagery of traditional Japanese ghost stories. The scene of a possessed lantern floating down an empty street is thrilling.

Ed Wood: Both his movies and the biopic. His love of movies shines through his work, despite his total lack of talent.

Hard to pick one MST3K movie but Jack Frost is my favorite. It's such a surreal journey through Russian folklore, made even funnier that the dub never agknowledges that the 'hunchback fairy' is in fact Baba Yaga! It's a movie where you go 'what the-' every ten minutes or so.