Hands down, the worst movie I have ever seen is The Marine with John Cena. I can't even tell you why I went to see it. I thought about walking out in the very first scene when a colonel saluted Cena (an enlisted man), but I stayed through the entire thing. The acting was so bad it was like they were trying to make it bad. And I couldn't get over the fact that Cena came out of the final, good-guy-versus-bad-guy climax with only had a scratch on his face and dirty clothes. This was after repeatedly jumping out of slow-motion explosions, taking a sledgehammer to the ribcage, and just straight up getting his ass beat. But I guess you can't ask for much from a movie made by WWE.
The worst movie I've ever seen had to be Muriel's Wedding. My wife wanted me to take her out for dinner and a movie and the dinner ran long. So when we got to theater there was a good action movie and this POS. She begged to see this piece of garbage and knowing I'd never get lucky again I went along. Two minutes into this I was wanting to gouge my eyes out. For the life of me I don't know why anyone would ever pay someone good money to make an absolute piece of crap as this movie. To this day she has never and will never, ever live this down.
Glamor Girls with the Duff sisters (Hillary and the other one). Made the mistake of sending my sister to the store to pick out a movie for us to watch. Hasn't happened since. Howard the Duck was probably worse, but at least it had plenty of character to somewhat make up for the total lack of acting and writing.
For me it was Battlefield Earth. It also had the funniest review I have ever read. "BATTLEFIELD EARTH is that amazing turd in your toilet bowl. That log of xxxx that has colors that you can't understand the reason for being there. It also has a weird shape... it somehow resembles something familiar. You almost want to take a picture of it to show friends late at night, when the blinds are drawn and have a dirty filthy thing you want to disgust someone with, but... you have this innate curiosity... "Have you ever seen anything quite like this?" As you can see there is a harsh language in the full review http://www.aintitcool.com/node/5937
Don't know about the best $20 I've ever spent. It ended up being pretty good but the cost to get there in mental suffering and anguish was very high. The best $20 likely went to a really hot petite brunette at the Gold Club after watching the Tigers lay a turd against Georgia this past season.