We start with the freshest, tastiest Malpeque oysters I've found south of Prince Edward Island. A side of sautéed spinach works splendidly as an appetizer, rich and intensely garlicky. And the meat—good Lord, the meat. Sliced sirloin in red wine sauce is a marvel of deep, beefy flavor. So is "W.R.'s Chicago Cut," an extraordinarily well-textured, bone-in rib eye. (It's named after Tribune food critic William Rice, whose glowing reviews line the walls.) Jack wants something to bag for our plane ride home, so after devouring his rib eye he orders a savory London broil—which he promptly polishes off. Jack can do that.
"Ready for the finale?" he asks. Our waitress staggers under its weight: a six-inch-high folly of macadamia nuts and vanilla ice cream encased in a crumb crust and topped with caramel and marshmallows—a culinary joke if it weren't so addictive. We light into it with steak knives. "Nothing like a Gibsons turtle pie," Jack mutters.
The crowd is as fun as the food. To our left are six girls who've flown in from Minnesota for Gibsons' surf-and-turf. "We're in mourning," one explains, pointing to her black-veiled companion. "She's getting married."
On our right sits a zoot-suited tough guy with a cigar in his breast pocket. He's sharing the 48-ounce porterhouse with a moll in a fur-strapped dress, who wears a diamond the size of a veal chop. "Nice ring your wife has," I tell Zoot.
"My wife's in Indiana," he deadpans. "And anyway, she doesn't like steak."
"Too bad for her," says Fur Straps, laughing and licking her lips.
In addition to the steak houses reviewed, we're including other favorites.
Strip House 13 E. 12th St.; 212/328-0000; dinner for two $90.
Dylan Prime 62 Laight St.; 212/334-2274; dinner for two $80.
Nick & Stef's Steakhouse 9 Pennsylvania Plaza; 212/563-4444; dinner for two $100.
Peter Luger 178 Broadway, Brooklyn; 718/387-7400; dinner for two $100.
Keens Steakhouse 72 W. 36th St.; 212/947-3636; dinner for two $100. Teddy Roosevelt loved it. So did Babe Ruth and Einstein. Those legendary mutton chops and a staggering selection of single malts are still served at this musty, manly 1885 institution. Dress nice.
Michael Jordan's The Steak House 23 Vanderbilt Ave.; 212/655-2300; dinner for two $110. On a balcony with a breathtaking view over Grand Central Terminal. Wealthy commuters miss trains by lingering over no-nonsense steaks (the porterhouse is sublime) and great wines. Polished and polite, and not at all the theme restaurant you'd expect.
Prime Steak House Bellagio Resort Hotel, 3600 Las Vegas Blvd. S.; 702/693-7223; dinner for two $150.
Charlie Palmer Steak Four Seasons Hotel, 3960 Las Vegas Blvd. S.; 702/632-5123; dinner for two $180. The famed cookbook author and Aureole chef goes back to basics with an unpretentious steak house that favors quality meats and subtle flavors over flash.
Delmonico Venetian Resort & Casino, 3355 Las Vegas Blvd. S.; 702/733-5000; dinner for two $130. Emeril Lagasse kicks it up another notch at the Venetian with Cajun-tinged side dishes, gorgeous rib eyes, and a melt-in-your-mouth chateaubriand.
Celestino Italian Steakhouse 8908 Beverly Blvd., West Hollywood; 310/858-5777; dinner for two $100.
Arnie Morton's of Chicago 435 S. La Cienega Blvd.; 310/246-1501; dinner for two $130. Morton's is Morton's wherever you go, but few carry the buzz of the L.A. outpost—just check out the Range Rovers six deep at the valet stand.
Grill on the Alley 9560 Dayton Way, Beverly Hills; 310/276-0615; dinner for two $90. The power-lunch spot of choice for meat-loving moguls. Bring an appetite, and a dozen copies of your screenplay.
The Palm 9001 Santa Monica Blvd.; 310/550-8811; dinner for two $100. Old Hollywood meets Old New York at this boisterous brasserie, where the steaks are presented simply and the dining room jammed with the fat cats and starlets whose caricatures line the walls.
Nine 440 W. Randolph St.; 312/575-9900; dinner for two $90.
Gibsons Steakhouse 1028 N. Rush St.; 312/266-8999; dinner for two $90.
Gene & Georgetti 500 N. Franklin St.; 312/527-3718; dinner for two $90. Frank Sinatra called it the best steak house in America. It even outlived him.