I have to say that Taylor listens to the faggetiest of faggy pop music. I think he does it initially as a joke, but actually likes that shit.
If the question was what is the gayest song of all time:
As for musicians I'm embarassed to like:
Rhianna, Jack Johnson, Fall Out Boy (pre-Infinity On High), Sugar Ray (Pre 14:59, and only because of what they later became)
Songs that come to mind:
Back For Good - Take That
I Want Love - Elton John
1,000 Miles - Vanessa Carlton