40. Kristen Stewart in Marcus Foster's "I Was Broken"
K.Stew's really is a beauty made for music videos. We can't get over the simple black and white cutaways to her and the sad, yet gorgeous, look on her face just kinda breaks our hearts. You know, kinda like Foster's song.
39. Jake Gyllenhaal in The Shoes' "Time to Dance"
No matter what role Gyllenhaal takes on, one thing remains the same: He's just a little bit off-kilter. He's got a little bit of the crazy eyes, you know? That works to his benefit in this clip, where he's having a mesmerizing yet creep murder fantasy. If it doesn't get your spine tingling, we're not sure what will.
38. Helena Bonham Carter in Rufus Wainwright's "Out of the Game"
The "Harry Potter" villainess pins up her hair and aches with romantic longing amongst the halls of the Dewey Decimal System. Helena lip-synchs along to Wainwright's vocals (so it obviously sounds a bit better than "Sweeney Todd") whilst the actual singer takes on not one but three library-dweller supporting roles. We can't remember the stacks being quite so entertaining.
37. Shia LaBeouf in Sigur Ros' "Fjogur Piano"
The Beef gives us the full sausage as he goes full frontal for the Icelandic band in this very NSFW video. In other words, it's seven minutes of LaBeouf in la buff. You're welcome.
36. Scarlett Johansson in Bob Dylan's "When the Deal Goes Down"
Like the song itself, ScarJo is transported back to the 1950s to recreate a time when the Internet never existed and Super 8 cameras were revolutionary technology. The combination of heartfelt and nostalgic makes this one of Bobby D's simplest, yet memorable, late-career entries.
35. Mickey Rourke and Jennifer Love Hewitt in Enrique Iglesias' "Hero"
If the corporate brass allowed it, we would somehow find a way to insert a video of Mickey Rourke beating a singer to death in every single listicle we do. Keep in mind, this was years before Rourke's big comeback when he was still wondering what exactly happened to his career and life. We'd like to think he exorcised some demons on Iglesias' head.
34. Angelina Jolie in The Rolling Stones' "Anybody Seen My Baby?"
It's not so much the running down the street in lingerie part that we find a little perplexing. It's that Sir Mick does what anyone looking for their object of affection would do: randomly sing a question to the nearest subway attendant. There is also an old guy grabbing his boobs for some reason.
33. Natalie Portman in Devandra Banhart's "Carmensita"
We don't really get too involved in the celebrity dating scene, but it's impossible not to mention that Natalie Portman started going out with Devandra Banhart after meeting him on the set of this bizarre, Bollywood-inspired video. We've seen this video 20 times and We're still trying to find the moment when Portman said, "Yep. I want that." It was one of the few times Brooklyn Vegan and US Weekly readers had something in common. Of course, she's since moved on to a ballerino, so there's that.
32. Jack Black in Beck's "Sexx Laws"
We feel like any joke we write won't be as funny as the video itself, in which a refrigerator has sex with an oven and a pink-pantsed zebra does a 360 with his human torso. And then it gets weird. Few people can turn Jack Black into an ensemble player, but Beck scores here.
31. Mischa Barton in James Blunt's "Goodbye My Lover"
Judging by this video, the UK singer-songwriter changed the title of this 2004 single from "I Know We're Breaking Up, But Can We Have Sex One Last Time?" to the slightly more elegiac current title. It's cool, man. Every guy's been there. Just usually not with Mischa Barton.