As much as I love Adam Sandler I have to say the worst movie I have ever seen is his Going Overboard. If you haven't watched it please take my word for it. I always try and at least finish a movie if I don't like it, I need to be able to say I sat through it. This I couldn't make it halfway through. Its horrible!!
http://www.youtube.com/watch?v=MKNZqnJ0hzU&feature=related
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National Lampoon's Gold Diggers. When I saw that Rotten Tomatoes had given it 0%, I had to give it a try. Anything that has no positive reviews has to be deliciously bad. It didn't disappoint (or did disappoint, rather. You know what I mean). It's a whole new level of horrible. Try reading the reviews on Rotten Tomatoes- some of them are hilarious.

It's also know as National Lampoon's Lady Killers.
Source(s):
http://en.wikipedia.org/wiki/National_Lampoon%27s_Gold_Diggers

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Unquestionably P.S. I Love You - a 'romantic' film where a young lady's fiance dies, but before doing so he creeply arranges years of 'gifts' and 'surprises' for her after his death, with the help of his mother-in-law?!?!? I ask you..
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Hands down...Santa Clause Conquers The Martians. When I was in college, the Student Association had an annual event where they showed the worst movies made to date. It was free to get in, but you had to pay to leave. This one was the one that cleared the theatre every time.

http://www.youtube.com/watch?v=XBRV7wGt3jU

You can also watch the whole thing on Youtube. At least you won't have to pay to leave.
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2001: A Space Odyssey. Seriously, the hour of whooping monkeys was just terrible. I don't care if it's called a classic. It's not.
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Titanic. Yes, the Kate and Leo one. It was wretched and LOOONGGG. About 3 hours into the movie I checked the time and realized that, in fact, only 1 1/4 hours had elapsed and there was almost 2 hours of film remaining. Most terrible movies would be wrapping it up at that point but this turkey was just getting rolling.

Luckily it was a rental and I could leave and go into another room and read.

My wife eventually forgave me.
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Haha...good question. I watched Jonas Brothers: The 3D Concert Experience with my little cousin. Sooooo painful.

But...the trailer is hilarious
Source(s):
youtube.

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MARS!!!!
Everyone are trying to come up with a support why their movie is the worst, but I'll say only one thing about MARS. I was pissed and angry for having wasted my time watching the movie.
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Great question!!

Every so often a group of my friends get together for a 'Bad Movie Night' and thus far the reigning champion has to be "Death Bed: The Bed That Eats" - http://www.imdb.com/title/tt0385639/

http://www.youtube.com/watch?v=BMkxVmLHIMk

Here is a slightly NSFW review of the movie as well:
http://www.youtube.com/watch?v=s3_KqAW_29w
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Gigli... I am embarassed to admit I ever saw it. So obvious their relationship wasn't going to work out.

http://www.youtube.com/watch?v=4-7iv6-8BRw

It actually won six Razzies:
Worst actor
Worst Actress
Worst Screen Couple (Bennifer - the start of the word couple name trend)
Worst Director
Worst Screenplay
Source(s):
http://www.ew.com/ew/article/0,,596113,00.html

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Megaforce. OMG this one was bad! Flying motorcycles outfitted with apparently recoilless rockets. Gold jumpsuits, the crotch of which get closeups.
This damaged a group of us so badly that we became a local MST 3000, openly laughing at the rubbish movies put out around that time.
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From the director of SNATCH (cool, I loved that movie)

Starring Madonna (well, she is a STAR)

The movie that gave them an excuse to go to Greece.

Swept away

http://www.youtube.com/watch?v=ZuJcTVfuGkA

Bad, boring and offensive.

I coulndn't even finish it.
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Bride Wars! I zoned out after five minutes. It fried my brain!
http://www.youtube.com/watch?v=bjsA0_arKtk
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To me, a truly horrible movie is not just awful, it makes you feel robbed for watching. I saw _Ransom_ for free and I still felt cheated.

There are some movies that are just dumb, and the people who make them know they are dumb, and people watch them when they want a dumb movie. Fine. No harm, no foul. In fact, a really campy bad movie can be enjoyable.

But some movies are awful but miss the so-awful-it's-hilarious chance at redemption. These movies insult the intelligence of the audience, and bore the audience while simultaneously trying to evoke great pity for and admiration of its characters. So here are the main reason why _Ransom_ is the worst movie I have ever seen (and keep in mind that I saw the Dukes of Hazzard remake). Spoiler alert: if you like horrible movies and want to see this one, don't read below.

1) A bad movie lacks talented actors. A truly horrible movie wastes great talents on horrible characterizations and plots. Mel Gibson, Gary Sinise, Lili Taylor, and Rene Russo are the actors, Ron Howard the director. Huge waste of talent. I actually felt pity for these rich and famous people.

2) The whole plot is a ridiculously convoluted mess. An elaborate yet uninteresting plot involving crooked cops working with criminals to kidnap a rich guy's kid. Every twist that was supposed to be mind-bending was either predictable or heavy-handed. The climactic scene was the a-hole businessman (Gibson) being inexplicably hardass when he figured out who the kidnapper was. After the kidnapper came to his house to collect the award for finding the kidnapper. And the little boy wet himself. Because criminal masterminds are idiots. And by this scene you are so unengaged with the suspension of disbelief that you don't feel sorry for the traumatized child character. You do sort of feel sorry for the child actor who has to go back to school after playing this part, though.

3) Character motivations make no sense. Mel Gibson's character decides to make a series of moves that would in real life get his kid killed right away. These flat characters are a big part of why the plotline is so ludicrous.

4)Female characters are all useless idiots. Rene Russo is helpless; she has no say in the situation, and her husband doesn't even think about what she thinks is the right move in protecting her son. When she does go against his wishes it goes very badly, and the kidnapper even acts aggressively in a semi-sexualized way. In other words, the father who doesn't listen to the authorities is a badass, The mother who does the same is a fool who puts herself in danger.

5) The nuanced actor Gary Sinise plays a caricature not a character.

6) There was just enough suspense to make you feel unpleasant, but not enough to keep it compelling.
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I think the worst film I've ever seen is called Zombie 4: After Death.

Yes. That zombie is using an M-16.
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I don't see a whole lot of movies - there just aren't many that pique my interest.

I did see Mortal Kombat: Annihilation, though. Holy cow, where does one even begin with a movie like that? It's clear that they made it just to cash in on the genuinely good first movie. And they went at the script with only one thing in mind: "How do we fit as many characters from the game in as possible?"

The answer? "By having 90% of them do nothing of note." There were so many characters, most of who(m?) looked awful. Shao Khan was especially bad. His actor always looked like every line he spoke could potentially make him go to the bathroom in his pants. The story was nonexistent and the CGI was atrocious. I went in knowing nothing about it save that I had lots of fun with the first movie, which is actually the only video game movie I'd call any good at all. And I left ANGRY. I had wasted good money on that movie. I was mad at the writers for churning out such bad dialogue, the film makers for producing it, and myself for SEEING it.
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Laserblast was by far the worst movie I ever saw. I concept of live humans interacting with aliens puppets completely escapes me. My wife and I were the only people in the theater.
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Scary Movie 2,3,4,5
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It's a tie betwen Very Bad Things and Erin Brocknovich.

Very Bad Things had it all - bad acting, bad plot, gratuitous almost-nudity. It was one step up from a softcore porn you'd see on Cinemax. Except that it wasn't even *good* softcore porn. It was just horrible.

Erin Brocknovich is the only movie I can remember actually leaving the theatre in the middle. A movie about a woman who just keeps making ridiculously bad choices, of her own accord, that we're somehow supposed to consider the heroine. A friend and I went to see it. 30 minutes into the movie, as we were both trying to poke our eyes out, the Dirty Biker Dude moved in next door. We looked at each other, and agreed - if she ends up sleeping with him, which would make NO SENSE and be completely contradictory to everything she's claiming she wants to do and be another ridiculously bad hcoice, then we're walking out. 10 minutes later, we walked out.
Source(s):
personal opinion

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First, I don't think one should list movies that are clearly made with no expectation that they are "good".. i.e. B-movies to Z-movies as the "worst" -- often times they are MADE to be bad, fully made with the expectation that they are going to be horrible. So, when the expectation is low, they often live up to your expectation...

So, if something was made with the expectation that they would be good.. and a lot of effort was put in... these are the ones that are most disappointing..

I'm surprised nobody has listed these yet...

Howard the Duck. A fairly decent comic book character, expected to be good based on the content of the comics. MILLIONS spent in production. $37-39 million dollars spent in 1986, which was a lot for a film at the time. according to http://www.filmsite.org/80sintro.html "the average film budget was over $18 million" So, if the average is just north of 18 millon.. one can see that it was a lot of money to spend on a film at the time. It basically killed the career of it's writing team and director, two people who had previously written American Graffiti and Indiana Jones and the Temple of Doom among others. http://en.wikipedia.org/wiki/Howard_the_Duck_(film)

Leonard Part 6 -- so bad it makes you wonder what happened to parts 1-5. So bad that Bill Cosby who wrote, produced and starred in the thing was panning the movie on tv and in interviews before it even came out! http://en.wikipedia.org/wiki/Leonard_Part_6

I will leave it up to everyone else to look up how many razzies and other bad reviews these films got. Let's just say, they didn't go.. unnoticed as bad.
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There are a lot of bad movies out there, but one that sticks in my head and made me think, "Why in the hell was this movie made??!!", was You Don't Mess With The Zohan. OMG that movie sucked. I think sometimes Adam Sandler tries too hard to be funny, that it just comes across as being way too stupid. And I really like Adam Sandler, but this movie was horrible.
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I once saw a movie called Schultze Gets the Blues which was truly vexing. It was one of those movies on the new release wall that has only one box - usually not a good sign. The premise was that this traditional polka accordion player from rural Germany is depressed and gets an itch to travel to america to a Zydeco festival, based on having heard a Album of Zydeco music. The premise seemed interesting, but the movie was truly painful.
Source(s):
Two hours stolen from my soul.

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The Blair Witch Project
I think the only thing I got out of the Blair Witch Project is an up set stomach. It, literally, made me puke!
(Make your enemy watch it on a big screen TV)
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In recent memory, Night on Rodanthe starring Richard Gere and Diane Lane. They had zero chemistry and the story was lame. I want my time back!
http://www.rottentomatoes.com/m/nights_in_rodanthe
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walle...no sound or talking for like 1 hour...
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300. Words cannot express the mind-numbing awfulness of this movie. At times I thought I was watching a Chippendales show, at other times a really badly acted sofcore porno. They lifted scenes straight from Gladiator and Braveheart, for instance, the serene walking through wheat fields scenes. Gerard Butler's accent even changed from Scottish to Roman to god knows what. The musical scores that didn't suck were similarly lifted from other movies.

If you pulled out just the coolest fight scenes and patched them together you could make an awesome 3-5 minute video clip, but as a feature length movie this was painfully embarrassing to watch.

300 dethroned Swordfish as the worst movie I've ever.
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