In the past I used to follow alot of MTV and similar televisions, and understand the style of some music videos director. Regarding the Pop music I think Britney is probably the one who use to work with the best music video directors, many of her videos are so good.
Jonas Akerlund, Jake Nava but also names like David Lachapelle or Floria Sigismundi (her videos for David Bowie, Sigur Ros, Marylin Manson etc are amazing...) or Chris Cunningham (Bjork's All Is Full of Love, Aphex Twin's Came to Daddy)
So there are a lot of great videos and there are some with a big impact like MJ's Thriller (great), Britney's Baby One More Time and others censored like the original version of Madonna's American Life or M.I.A.'s Born Free...
But my favorite video ever is probably Gwen Stefani 'What U Wating For'. They create some of the contemporary popstar which are copycats of Gwen in this video, like the various Gaga...
LOL actually I also did an exam at the Uni about the influence of Music Videos and Pop Culture in contemporary Visual Arts...
This is a music video that rates up there with classics like Aphex Twin's Windowlicker. You almost never find a story this intense and emotional in a music video. It's reallynot what you're expecting from a music video.
I'm really liking that "Headlights" video from Eminem, mostly because he actually reunites with his estranged mother in it and apologizes for any of the hurtful things he's said about her over the years.