1. Cruel Intentions (1999)
I still can’t believe there’s a movie about a girl making a bet with her stepbrother that if he can get a virgin to sleep with him, he can also sleep with her. Not only does it exist, but it has everyone that you loved in the ‘90s all in one place.
2. Freaky Friday (2003)
In the third, but definitely not the last, version of Freaky Friday, Jamie Lee Curtis and Lindsay Lohan switch bodies. Can you imagine if this actually happened? I don’t see Lindsay being content peddling yogurt on a daily basis.
3. The Mummy (1999)
Let’s be honest, none of the movies in The Mummy franchise are particularly good, but I swear I can’t turn on my cable box without seeing it on. What’s even worse is that I can’t bring myself to change the channel once I start watching it. You win this round, Brendan Fraser.
4. Anaconda (1997)
The special effects are beyond bad and it’s full of some of the worst performances you’ve ever seen, but you know you love it. There may not be a better moment in movie history than when Jon Voight grabs J-Lo and awkwardly kisses her. The whole movie is just so bizarre.
5. Hackers (1995)
It’s probably safe to assume that Angelina Jolie will not be doing a sequel to Hackers. This movie came out just before computer terminology became common, and is full of some of the most incorrect and ridiculous “hacking” terms you’ll ever hear.
6. Wild Things (1998)
My teenage years were forever impacted by that scene with Neve Campbell and Denise Richards in the pool. Matt Dillon should have just retired after this, because there’s no way he could ever top this movie.
7. White Chicks (2004)
The Wayans have mastered the art of making tons of money by feeding an audience some of the most poorly written jokes imaginable, but nothing will top 2004’s White Chicks. I can’t take Terry Crews seriously in anything else because I just picture him singing “A Thousand Miles” every time.
8. Mannequin (1987)
If you think about it, how creepy is the plot of this movie? A guy build a mannequin and then falls in love with it? It’s completely absurd, but Andrew McCarthy is wonderful, plus James Spader is in it!
9. Serendipity (2001)
The entire movie may be completely outlandish and ridiculous, however you’d have a hard time not cheering for John Cusack and Kate Beckinsale to find each other, fall in love, and have a bunch of babies.
10. Showgirls (1995)
Elizabeth Berkley sheds her Jesse Spano image in dramatic fashion, as a stripper named Naomi trying conquer the Vegas showgirl world. Her big sex scene couldn’t be more cartoon-like if it were with Spongebob Squarepants. I still love you, Jesse Spano.
11. Drumline (2002)
Nick Cannon shows us the dark underworld of playing the drums in a college marching band. It’s basically Step Up for bands. Do you think this is when Mariah knew she was in love with Nick Cannon? I hope not.
12. 13 Going on 30 (2004)
We can all admit this is exactly like Big, right? Still though, it has just enough ‘80s references along with Jennifer Garner and Mark Ruffalo starting a choreographed Thriller dance to make it a guilty pleasure anyone will enjoy.
13. Kindergarten Cop (1990)
Arnold was in that awkward phase of his career when he was doing action movies as well as family comedies, so it was only natural to combine the two. Toss in a group of adorable kindergartners and you’ve got a very bad movie that’s impossible not to watch every time it’s on.
14. Weekend at Bernie’s (1989)
Andrew McCarthy shows up again on the list and, instead of falling in love with a mannequin, he parades his dead boss’ body around a bunch of parties to keep up the illusion that he’s still alive. Not only is this highly illegal, but I’m fairly certain it violates numerous health code regulations.
15. A League of Their Own (1992)
It’s the sports movie for those who don’t like sports movies. A League of Their Own features a brilliant cast, led by Tom Hanks who is as charming as ever. By the way, who would have ever thought Madonna would appear in a movie as a baseball player?