Well since we have one for movies and TV shows, why not have one for music artists or songs. Again some people might get a bit upset, but you shouldn't take people opinions so hurtfully. Let's debate friendly...
Here's my thoughts...
Madonna- I'll never truly understand her appeal and why people regard her as a "legend."
Ke$ha- She writes some of the WORST lyrics ever and needs an auto tuner for her "singing" or "rapping" or whatever she's trying to do excatly.
I completely understand what you're saying but I also can explain the appeal of these two artists.
Madonna has proven longevity - not through true innovation, but by embracing the music industry on every commercial level. For better or for worse she helped create the pattern that most recording artists now follow. Her music isn't quite poetic, but it does strike a chord with club culture and once you have that the rest follows. She has mastered the art of keeping up with current trends and branding them as her own. I still don't think she's done much good since 1990. I can understand why some folk never bought into her hype. She does work pretty hard with what little vocal chops she's got. Her drive is why she's still around while others fell away. Not saying it's a good thing.
Ke$ha is all tongue-in-cheek. Say what you want about Gaga, but that woman can actually sing and play an instrument quite well. That's saying a lot these days. Ke$ha on the other hand is all kitsch and pop. She has maybe one more album in her - tops. Still, she's fun.
Personally, I dig music for different reasons but most of all I like it for how it makes me feel. I'm not one for Barbra Streisand or gloomy ballads. I either like up-tempo or angsty music like Rancid or the Ramones. I find both to be proactive. I'll listen to the odd ballad now and again. Cyndi's one of the select artists whose ballads I'll listen to. Something much more raw and heartfelt than an over-the-top Barbra tune. Yes, I admit to being one of those gays who doesn't think much of the Funny Girl.