1. What Girls Want by Material Issue:  Okay, I’m already embarrassed about this one.  Mostly because it is a very dated style that I can’t remember why I liked, but I did (in high school, though – I was young and stupid then).  And generally the lyrics portray women to be pretty flaky and senseless … but to a peppy beat.
2. Heterosexual Man by The Odds:  This one I’m actually not at all embarrassed about.  This is not really negative towards women so much as pointing out how sex-driven man can be.  The characterization is sadly not far from the truth.  I first saw the video on 120 Minutes on MTV (back when they still showed music videos) and was hooked on the song and the band.
3. Closer by Nine Inch Nails:  Again, this one doesn’t really demean women, but it portrays men as essentially a a few social conformities away from screwing anything that moves.  The video was f-ed up, but in a kind of awesome/train-wreck kind of way.
4. She Hates Me by Puddle of Mudd:  As with others, I had gotten hooked on this song due to the video – I loved the build up with the fry cook and the kid in the classroom.  And whenever the song comes on the radio in my car (when I’m alone) I can’t help but belt out every word at the top of my lungs (the unedited lyrics of course).  And for those who are unaware, the theme of this song is of a guy pissed off about being blue-balled.
5. Darling Nikki by Foo Fighters:  I know this is a cover of a Prince song, but I heard this version first and enjoy it a lot better.  Unfortunately, Dave Grohl wasn’t proud enough of this performance to include it in any U.S. releases and the only videos I could find were concert footage.  I suppose this song doesn’t really depict women badly so much as depict a questionable member of the gender (though that is even debatable depending on your stance on acceptable behaviors).

I’m sure there are plenty of raunchier songs out there, but these are my picks.  If you’ve got some, feel free to add your thoughts.