Photo credit: Ron Faiola
A trip to the supper club for Milwaukeeans often means taking a drive out of the city, to a spot like Hobnob in Racine, Schwarz's in New Holstein, or even Ishnala in the Dells. Taking the time to get to these far-flung supper clubs adds to the feeling that dining at one is a special occasion-worthy event.
But there are times when we want the familiar comforts of a supper club without the long drive. That's when Jackson Grill fits the bill. It's got almost all the classic hallmarks of a traditional supper club and it's tucked away in a residential neighborhood on the South Side.
Jackson Grill occupies the main floor of one of the old mixed-use duplexes that are so ubiquitous in this part of town. When you walk in, it does feel like you're in someone's living room, despite the fact that the U-shaped bar takes up half the space. The walls are wood paneled, the bar top is Formica, and it all feels straight out of the 1950s. Above the backbar is a colorful collection of glass vases that's lit from beneath, creating a rainbow glow in the dim space. On the opposite wall, above a few high-top dining tables, are framed signatures of some of celebrities that have dined here, including Bob Uecker and Bud Selig—who happened to be celebrating his birthday here.
Just off this magical bar room is the dining area, which is small and feels more dated than retro with its double tablecloths and heavy swag window treatments. Luckily, a large picture window (with more vases on the sill) makes this space feel airier than the dried flower arrangements on the walls let on.
Steaks are the main draw here, like most supper clubs. The fattier cuts like a bone-in 24-ounce ribeye ($46) and a 16-ounce New York strip ($35) arrive with a thick, deeply blackened crust. This is a restaurant that doesn't shy away from charring the exterior of your steak, much to their credit. When ordered rare, it creates a dichotomy of texture and flavor, with red, supple beef and a crunchy, slightly bitter char.
The filet mignon (6-ounce for $26, 10-ounce for $36) gets slightly less of a crust in order to keep its tender texture throughout. Like all steaks here, it's from Black Angus cattle and comes topped with a white grilled portabella mushroom cap and a clove or two of roasted garlic. Anyone who prefers a sauce with their steak should consider the tournedos au poivre ($32) with three peppercorn-crusted medallions and a creamy red wine sauce.
All steaks come with soup or a very respectable house salad with baby greens. This is one of the few spots where you can still find hot bacon dressing—and made with Nueske's to boot. You also get a side dish; the heavy garlic mashed potatoes come in a ramekin and are more starchy than creamy but great with the rich beef, while the broccoli is served as a steamed whole head with thick cheese sauce.
Besides steak, the rest of the entrée menu includes saucy barbecue ribs ($28), “purgatory shrimp” ($23), served in a spicy tomato sauce over pasta, and a heavy pasta carbonara ($19). Scallops (market price) are seared, served with a seasonal risotto and always exceptional.
One way Jackson Grill differs from supper clubs is the lack of a relish tray, but the few appetizers offered make up for it. Escargot ($12) comes with grilled sourdough to sop up the garlic butter, and thin French fries are cooked in duck fat. Oysters, crab cakes and a generous plate of eggplant strips with marinara are also offered occasionally.
Desserts tend to be simple classics as well. Strawberry napoleon has layers of flaky puff pastry, custard, sliced strawberries and whipped cream. Bananas foster is full of cinnamon and served over ice cream, while crème brulée often has Butterfinger candy additions.
The Old-Fashioneds here are muddled and delicious, just like you'd expect, but if you're looking for an after-dinner drink, try the Jackson Grill Snifter. It's a mix of Frangelico, Irish Mist, Grand Marnier, Tia Maria and brandy. Do everyone a favor and sip it at the bar, because tables are in high demand and it's so easy to sink into those tufted black barstools for the night.
