right now I'm with crazyguy. I don't really see any of Timberlake's music lasting longer than a decade, but I guess time will tell.
As for Steamroller, I do really enjoy it, in fact I've yet to find the James Taylor song that I don't like. But "something in the way she moves" (the slower version), "Carolina in my mind", anything from Mudslime Slim and the Blue Horizon album, "Sweet Baby James" and "Song for you so far away" are songs that immediately come to mind for me. "Song for... away" is possibly my second favorite song of all time. Behind only "Melissa" by the Allman Brothers and maybe, just maybe "Name" by the Goo Goo Dolls.