Macadamia Turtle Pie at Gibsons Bar & Steakhouse
Most of these desserts should come with a semi-serious warning like this one did; in fact, our waitress warned me and my dining companion (fellow SE contributor Dennis Lee—heyyy!) no less than three times that this would be way too much for two people. Of course this quarter of a pie would be too much for eight people. She later dropped off the slice and patiently waited while I snapped a few photos. When she came back to carve a slice out of the slice with the embedded steak knife, she had to wrestle it out Excalibur-style. At first bite I was a little disappointed by the standard vanilla ice cream and macadamia nuts, but I was sold when I finally got a bite with the cinnamon-laced crumbly crust. If there were only a more proportionate amount of it, this would be one formidably delicious dessert.
"Legendary Sundae" at Morton's The Steakhouse
Yes this is simply a molten chocolate lava cake drizzled with caramel and chocolate, topped with vanilla ice cream, whipped cream, and a cherry. I know. Yawn. Except this was hands down my favorite dessert. In fact, I'm a little ashamed to admit this is probably in my top three favorite desserts in the city. The cake is outrageously well done: crispy on the outside for a great textural contrast and chocolate syrupy on the inside. My father, who I dragged along with me, was going to be late to work, but we literally couldn't stop ourselves from frantically shoveling every last bit of this thing into our mouths.
Cake in a Can at David Burke's Primehouse
David Burke's red velvet "Cake in a Can" is an experience all its own. First off, it takes so long to bake, you have to give the kitchen fair warning and order it at the beginning of your meal. Then they start you out with a little amuse of cake batter on a beater. Next the cake is slathered with buttery, tangy cream cheese frosting right before your eyes and then carved up tableside like a piece of meat. The frosting gets almost soupy and blends in deliciously with the springy, still-crusty cake. Just to push it way way over the edge as these steakhouses are wont to do, it also comes with four scoops of vanilla ice cream.
23 Layer Chocolate Cake at Michael Jordan's Steakhouse
MJ's famous number gets translated into chocolate cake and mousse in this towering slice of cake. It's fun to eat it layer by chocolatey layer, but absurdly, this thing still left me wanting—for more whipped cream and hazelnut brittle. The proportions of accoutrements to cake are logical aesthetically but comical when it actually comes down to eating the cake. Luckily the service is classic and almost as over the top as the cake so if you ask for more of either, the request will be accommodated in the blink of an eye.
Havana Dream Pie at Joe's Seafood, Prime Steak & Stone Crab
Joe's version of tres leches cake puts thick and cool custard between two soaked slices of vanilla cake and then drizzles the entire slice with caramel (of course). Combined with strawberries, it becomes a more multidimensional take on strawberries and cream.
Warm Butter Cake Mastro's Steakhouse
Last but not least: the dessert that kicked off my search. You can't get much more over-the-top than a cake with "butter" in the name, which is topped with ice cream and which comes with a tagalong dish of real whipped cream. The rich, custard-like middle of the cake is cut by accompanying strawberries, syrup, and a nice crunch from bruleed sugar over the top.