Again, this list is limited to movie theater experiences, and relationship issues to do not factor into the rankings.
Bless the Child (2000)
Joe Dirt (2001)
These can all be lumped together. Each are awful movies, plus the experience was made worse because I convinced others to spend money on them. "Hackers" was the first time I led a group into a shitty movie ambush - there may have been 8 or 10 of us in total, and I promise you every one of them hated it. I guess I expected something akin to "Sneakers", which I'd seen over and over on VHS. "Sneakers" is still awesome, and while "Hackers" now has a cult following that I pray is ironic, it still sucks big time.
"Bless the Child" starred Kim Basinger and Jimmy Smits, and somehow that didn't set off red flags. The commercial was kinda spooky and cool, with the little girl actress saying something about the end of the world or -- I don't know, it was a total misfire on my part, and I convinced a friend to tag along, and maybe that's why he doesn't return my calls nowadays.
Do I need to say anything about "Joe Dirt"? I will anyway. I laughed every time the commercial aired, when David Spade put up his fists and said, "Why don't you say it into the microphone?" Sure, we knew Dennis Miller was involved, but this was before everyone was positive he turned crazy. Christopher Walken was billed, but he ended up with a very small part. After my 2 or 3 friends and I got out of the movie, we drove to Applebee's. ("Applebee's Eases The Pain" was the chain's slogan at the time, if memory serves.) I swear to God this happened: our waitress came back with our drink orders and asked why we looked so dazed. Joe Dirt literally put us in a stupor! We explained how bad the movie was, and I told her that I recognized her from not one but TWO places - she sangs sometimes at the church I attended, and I'd just seen her do some musical theater for the Music Listening Lab class I was taking for some art credit requirement. I quoted some of the song she sang in her musical scene, to add super stalker bonus points. As we were driving away, I realized I was responsible for our party's tip, and I hadn't left her anything -- again, Joe Dirt had scrambled our brains -- so I executed an erratic U-turn in the old Honda, ran inside, found her, and apologized and left some money. So yeah, I had a pretty good-sized crush on her.
Snake Eyes (1998)
Just after "The Rock" and "Con Air", my friend and I made a ridiculous pact to always watch Nic Cage movies together, so we got together to see this piece of crap. In modern times, it would be obvious that Cage would star in a piece of crap; back then, it was a huge disappointment. One of those suspense movies where you think, "Gee, that guy would be a really obvious villan, surely it will end with some other twist," only it doesn't.
The Thin Red Line (1998)
This movie came up the other day when Adrienne said she was excited for "Tree of Life", the new Terrence Malick movie to be released soon. I mentioned it was the first and only movie I ever walked out of - let me set the scene. 1998. "Saving Private Ryan" came out earlier in the year, which stoked everyone's interest in war-related films. My girlfriend and I decide to double date with Phil and his girlfriend, and we gentlemen choose this movie. We arrive late to a crowded theater (I told you everyone's interest was stoked!) and sit in the front row. The movie starts. Adrien Brody swims around on an island for a while. The army finally shows up. They walk around on Guadalcanal. Lots of shots of tall grass blowing in the wind. In what passes for an action scene, Woody Harrelson's ass is injured by a grenade. I remember being bored, and uncomfortable because the decision to subject the women to this movie was partially mine. We all look at each other, and decide our time can be better spent elsewhere. As we leave, we hear a girl wishing she was leaving, too.
Harry Potter and the Sorcerer's Stone (2001)
Hadn't read the book, theater full of little children, popcorn EVERYWHERE, too long...
The Punisher (2004)
I didn't care to see this, but my friends wanted to. I sat down in a row with available seats for all of us, but they kept walking up the steps, and sat in a row that only had enough seats for them. It was real bullshit.