Almost ten years ago now I went through a David Bowie phase. It began mostly because of Trent Reznor's involvement with I'm Afraid Of Americans was most pleasing to my twelve year old ears, which were in the process of falling deeply in love with all things Nine Inch Nails. I figured that if Reznor liked Bowie, then I'd like Bowie. Scratchy MP3s of Bowie playing live with NIN further reinforced the notion that I should probably be listening to David Bowie.
I ended up buying a copy of Earthling and even though I didn't understand it---the fact that it was basically Bowie trying to cash in on electronic dance music (fans call it "reinvention", detractors call it "desperation") when I was currently mostly intrigued by industrial music left me wanting, and I thought the non-Reznor mix of I'm Afraid of Americans was pretty much terrible---it still made me want to dive into Bowie.
1. Outside really did it for me. This was an album that was dark and hard to understand, basically as close as Bowie would ever get to sounding like Nine Inch Nails, which wasn't close at all. Even to my twelve or thirteen year old ears, I could hear that there was something strained about it. Fact is, if you really listen, after 1983 pretty much everything David Bowie does feels kind of strained and labored. (This notion is further reinforced by his public statements that in the 80's he was just a big sell out.)
As a related aside: China Girl is probably one of the most obnoxious songs I have ever heard.
I hardly listen to any Bowie anymore. I think I just grew out of it. I can read a song list and sing parts of every Bowie song imaginable in my head for the most part, but my days of actually sitting down and listening to Bowie albums has passed. David Bowie, Radiohead, Aphex Twin, and Garbage, four artists I listened to in my youth that I no longer have the stomach for. It's kind of sad, really.