When one is faced with RPM’s ambitious—and pricey—steak menu, momentary paralysis is natural. Does one splurge on a 36-ounce rib eye that’s been dry-aged for 90 days ($165)? Or perhaps three ounces of Hokkaido Snow Beef, an ultrarare variety of wagyu ($150)? What about the eight-ounce Colorado bison filet ($51)? Then there are the add-ons: Béarnaise? Bordelaise? Foie gras butter?

The good news is we’ve never had a bad steak at RPM. The Duke, a crispy-crusted rib-eye filet ($55, above), is especially memorable, as are the three precious ounces of creamy pink Miyazaki ($93). Most often we saddle up for the dry-aged 24-ounce cowboy steak, an $83 prime bone-in rib eye oozing with fatty, smoky flavor.

This sleek, cream-toned lair from Lettuce Entertain You has such a spendy vibe that the poised servers barely have to upsell the sides, like roasted Japanese sweet potatoes, or the desserts, like the de rigueur baked Alaska, which is flambéed tableside. The treasures at RPM feel boundless—particularly for those with expense accounts to match.

Tip:Customers celebrating birthdays—or rogues pretending to—get enormous clouds of homemade cotton candy.