Originally Posted by
ambergris
Well, some artists are hard to classify. The core period of Bowie's talent is only ten years: 1971-1980. But that leaves out Space Oddity and his biggest hits, from Under Pressure to Absolute Beginners. Also, Hunky Dory was a commercial failure at first, but now it's a classic. The Man Who Sold the World also turned into a classic, thanks to the Nirvana cover. And yes, Bowie's revival in the 90's was also important, but with less cultural impact. It's the same with Bob Dylan's comeback since Time Out of Mind. He also had terrible 80's, but Bowie was at least still successful and a cultural force.
About Madonna, she was probably Pop music's biggest solo star after Michael Jackson turned weird. Yes, her songs often are easily digestible pieces for pure entertainment, but somehow she managed to direct modern culture for about 20 years with that - from Like a Virgin in 1984 until, probably, Hung Up in 2005. I just want to add that there are not many artists who would have made a song like 'Frozen' into a hit. That says something.