Hyde Park's Caribbean-focused Calypso Cafe, along with the now defunct New Orleans-inspired Dixie Kitchen, is a favorite of the First Family. They recently added some of the more popular dishes from Dixie Kitchen's menu—which just happened to be the President's faves—including peach cobbler, fried green tomatoes and the Southern Sampler (Jambalaya, gumbo, red beans & rice).
Italian Fiesta, in South Shore, had the honor of serving its thin-crust pizzas at the inauguration. This is the way a pizza's supposed to be: indulgently greasy and bursting with flavor from hearty toppings. Obama's guilty pleasure is the cheese-only pizza.
He's fit as a fiddle and his waistline is trim and slim, but we love that he's not afraid of chowing down on an occasional sandwich loaded down with mounds of corned beef. He caused quite a scene when he ordered several, and paid cash, at Manny's Deli right after the election.