From Food Network
Wisconsin is considered to be the birthplace of “supper club” dining, and Five O’Clock Steakhouse, Milwaukee’s longest-running steakhouse, pays homage to those traditions with the style of service it’s offered since 1946: Servers take orders while diners are having a drink at the bar (don’t miss the signature Brandy Old Fashioned, considered the state’s unofficial drink), and when diners sit down, the table is set with a family-style salad; a relish tray with olives, onions, pickles, carrots and peppers; salad dressings; and warm sourdough bread and a honey bear. All steaks, including the signature 16-ounce center-cut filet mignon and the 21-ounce bone-in rib eye, are basted with a signature, top-secret char sauce and finished au jus. The old-school North Woods supper club vibes are echoed in the decor — the restaurant sits in a historic early 1900s building with a hand-cut limestone facade, there’s dark wood paneling throughout, and the Christmas lights and decorations are a year-round fixture. Rumor has it that throughout the ’50s and ’60s the restaurant’s Alley Cat Lounge was an underground gambling parlor where people would sneak in through the rear alley entrance; these days, though, you’re more likely to catch a live show here than a gangster.