
Taylor Swift, “You Belong With Me” (Fearless, 2008)
Plenty of pop videos have used the “entire teen movie in three and a half minutes” schtick, but that isn’t what makes this one seem dated. Rather, it’s the giant glasses sported by our heroine, Nerdy Taylor. I can’t speak for the rest of the country, but in Brooklyn those giant specs are so ubiquitous they barely even register as nerdy anymore.
From Audrey Hepburn in My Fair Lady to Rachel Leigh Cook in She’s All That, the Pretty/Ugly Girl plot arc has always been a transparent sham, but here the snake seems to be eating its tail. Nerdy Taylor, Prissy Taylor, Post-Makeover Taylor — all of them are, inescapably, Taylor Swift, who is more beautiful and popular than we will ever be (no matter how big her glasses are). Us regular slobs understand which Taylor we’re supposed to root for; we just don’t quite identify.
Avril Lavigne, “Girlfriend” (The Best Damn Thing, 2007)
I don’t mean to be down on Taylor Swift; “You Belong with Me” is actually my favorite of today’s three clips, if only because the kid really does seem to mean it. You know she’s not the frumpy band geek she claims to be, but you still want the best for her — the story traces a clear line from emotional conflict to happy ending. Not so with Avril Lavigne’s entry in the canon, which lacks even a single likable character. Who’s our champion here — the fussy, possessive ice queen; the bullying boyfriend-stealer who’s into dark eyeliner and physical assault; or the “aw, shucks” pretty boy who will flash you a grin as you tumble downhill into a pool of human excrement? To paraphrase Brad Neely, people like these are the reason that God doesn’t talk to us anymore.
Mariah Carey ft. Jay-Z, “Heartbreaker” (Rainbow, 1999)
Late-period Mariah Carey is best known for being a little unhinged, so giving her multiple personalities and having them kung-fu fight is a pretty good fit. But her personalities seem a little crazy themselves: Good Mariah dresses like a twelve-year-old and spends the video careening through mood swings, from sad-eyed stoic to beaming bootyshaker to vengeful beeyotch. Evil Mariah powders her cleavage obsessively, yet even in a mirror, she fails to notice the clump of popcorn spot-welded to the top of her head. And in the end, they both lose for thinking Jerry O’Connell is worth fighting over.
Homegirl sure knows how to belt it, though. Respect.


