17. Adam Sandler
The ultimate "love him or hate him" guy. Sorry — Operaman alone would make him rank high on this list. Sandler was the first to get a Boston-Irish accent right on national TV ("Get into the faaah left lane, then take the Mass Pike west and you'll see a wicked-huge Radio Shack"), which made him a local hero, even if it set off a very unfortunate comedy trend. Weirdly forgotten historical footnote: Everybody assumed Sandler was gay, because his first memorable bit was about coming out to his family on Thanksgiving. That made him seem edgier than he turned out to be.
Greatest hit: "The Chanukah Song," a major cultural event. Seriously, nobody had any idea Shatner was Jewish.