Hoople - 12:32 am on May 12, 2011 (gmt 0)
My second oldest site (1997) is still up. Although the video chat program it was about has since faded into obscurity with java web modules now in fashion. Nested tables no less!
Never monetized, but the free host does have some AdSense on it. Has only lost a bit of toolbar rank, at PR4 now surprisingly.