The oldest still-operating restaurant in New York City, still in the family of the original founders. At Christmastime, it's decorated to the nines. Go with a big group: portions are large and the wine flows liberally. Look for the little buttons on the walls: in the old days, the mafia would hang out in the back room, and if diners saw the cops come in, they'd press the buttons so the mafia guys could run out the back.
If I lived closer to the West Village I’d go over to Jack’s every morning for a coffee and occasionally having what is probably the best chocolate chip cookie in New York (and it’s just a dollar!). Even though it’s rarely in my way I try to go here now and then, maybe in combination with a stroll down the beautiful Bleeker Street or to read a book sitting in their window.