1. Destiny’s Child, “Independent Woman Part I”/Charlie’s Angels
Somehow mentioning “Lucy Liu, with my girl Drew, Cameron D. and Destiny” didn’t totally lock this song into a box; it made the entire “Charlie’s Angels” bootcamp that Destiny’s Child attends in this video that much more awesome.
2. Wheatus, “Teenage Dirtbag”/Loser
The most confusing thing about this video is that it’s for the movie Loser with Jason Biggs and Mena Suvari, who were ALSO in American Pie together. Since far more people have seen American Pie, a lot of people think this video is for that movie. Maybe it was a conspiracy to try to get anyone to see Loser.
3. Will Smith, “Men in Black”/Men in Black
If you’re going to make a movie with Will Smith and he’s supposed to be wearing black in it, you should make a video where Will Smith is a man singing about wearing black.
4. Wil Smith, “Wild Wild West”/Wild Wild West
It’s like they took the plot of Wild Wild West and sort of jerked it around and then made a super-long music video about it. Stevie Wonder shows up! Enrique Iglesias plays a prince! Sisqó is there too!
5. Britney Spears, “(You Drive Me) Crazy”/Drive Me Crazy
Spears plays a mildly cracked out waitress, and then the camera pans a lot to Melissa Joan Hart and Adrian Grenier who are smiling and hanging out and just generally happy to be included.
6. Beyoncé, “Work It Out”/Austin Powers in Goldmember
This marks the beginning of the reign of Beyoncé’s hair at her very best, and the moment we learned she can Hula-Hoop like no other.
7. Nickelback, “Hero”/Spider-Man
8. Quad City DJ’s, “Space Jam”/Space Jam
Most commonly known as “that Space Jam song,” Quad City DJ’s actually wrote this song, producing a video that is almost as good as the movie, complete with breakdancing.
9. Madonna, “Die Another Day”/Die Another Day
This music video cost $6 million to produce, which is weird because Madonna is just really dirty and wearing a wifebeater in it.
10. Linkin Park, “New Divide”/Transformers: Revenge of the Fallen
Woah it’s like first you’re looking at Linkin Park and then all of a sudden they’ve transformed into a Transformer!
11. Guns N’ Roses “You Could Be Mine”/Terminator 2
Impressive solely based on the presence of Arnold Schwarzenegger.
12. Ronan Keating, “When You Say Nothing At All”/Notting Hill
What a sad sack of a video about love, made that much more unimpressive by the awkward interspersing of scenes of Julia Roberts and Hugh Grant hugging and stuff.
13. Tina Turner, “Goldeneye”/Goldeneye
TINNNA. Now THIS is how you do a James Bond movie music video.
14. Blaque, “As If”/Bring It On
This would be just your typical “insert scenes from the movie that have nothing to do with the plot of the video” except that the edits are done in such a way so that Blaque is often making faces at the characters of Bring It On, and vice versa.
15. Jennifer Hudson & Ne-Yo feat. Rick Ross, “Think Like A Man”/Think Like A Man
It’s pretty clear that Ne-Yo has some sort of sex-in-the-office fantasy that HR at any company would disapprove of (just see “Miss Independent”). Why he had to involve those feelings into the video for movie that was already relatively sexist is unclear.
16. Whitney Houston, “I Will Always Love You”/The Bodyguard
It’s astounding that the most famous version of this song is forever attached to a movie where Whitney Houston and Kevin Costner were a couple that made sense.