Jackson Grill (Part One)

In this three part series, TCD will visit three supper clubs in Southeast Wisconsin and provide you a comprehensive list of supper clubs in the region. 

There is something about Wisconsin supper clubs that feels homey and festive. Perhaps it’s because many who grew up in rural parts of the state have fond memories of family gatherings at the local supper club. Although this particular breed of dining establishment seems old-fashioned, and arguably inching toward extinction, they are undoubtably still revered and synonymous to Wisconsin’s past and present.

The first American supper club was created by Milwaukee native Lawrence Frank in Beverly Hills, Calif., in the 1930s. Live music and dancing entertained the crowd while Frank served up elegant cuisine. It was a place for stars and socialites to see and be seen. The décor was classy: Art Deco, white linen tablecloths and dark wood. The signature dish was prime rib with a side of mashed potatoes and vegetables—a staple in Wisconsin supper clubs.

Soon after, supper clubs began to pop up all over the state of Wisconsin. Many early supper clubs in the upper Midwest were originally roadhouses and speakeasys during Prohibition and served gangsters and bootleggers returning from Canada. When Prohibition was lifted in 1933, liquor licenses were granted first to establishments outside the city limits, perhaps explaining the off the beaten path locations of supper clubs.

Architecturally, supper club designs were often bold and eye-catching. Some took on exotic themes like nautical, tiki, or hunting lodge. The most distinctive-looking was the Gobbler Supper Club and Motel in Johnson Creek, built in the late 1960s. The business closed in 1992 but the starship-like Googie style architecture still remains. The Gobbler had purple furniture and carpet and a rotating bar. Most existing supper clubs today opt for a simple atmosphere over extravagance.

While the definition of a true Wisconsin supper club is up for debate, they all share a few undeniable characteristics.

A Wisconsin supper club is family owned and operated by longterm employees. The menu is simple and entrees come with soup or salad and with a side of potatoes or vegetables. Perch fish fry is offered on Fridays, and prime rib on Saturdays. The location is always a destination, and there is always a bar separate from the dining room where the staff knows exactly how to make a true brandy old-fashioned. Some offer a complimentary relish tray while others list it on the menu to order.

In recent years, a few new establishments have taken on reinventing the Wisconsin supper club. In 2005, The Old Fashioned opened shop on Capitol Square in Madison. Not only do they give a nod to the traditional supper club, they also sets out to celebrate all that Wisconsin has to offer, from local microbrews, cocktails, cheese, meats and produce. Milwaukee’s Bartolotta Restaurant group opened their own supper club concept, Joey Gerard’s, just this year. There is one location in Greendale and another in Mequon. The Bartolotta’s concept is a tribute to the supper club culture as a whole. The decor style is a fine blend between Midwest northwoods and classic Californian, and they offer a selection of tiki drinks, ice cream drinks and cocktails popular in 1958. The Old Fashioned and Joey Gerard’s both brought back the tradition of the plethora appetizer samplers served on a lazy susan, which was at one point a fashionable offering at Wisconsin supper clubs. These are perhaps the new generation of the supper club. With establishments who pay respect and don’t trivialize and exploit the understanding of the supper club, there is definitely room for more variations and improvisation.

Jackson Grill, located on the south side of Milwaukee, is a shiny gem nicely tucked into the residential neighborhood of Burnham Park. Despite being in business for less than 15 years, it has become one of the city’s iconic establishments. Owned and operated by Chef James (Jimmy) Jackson and wife Heidi Schmidt, Jackson Grill is by any definition a mom-and-pop restaurant. They treat their employees like family and most have been there since day one. Heidi works side-by-side with her servers and bartenders each night. She serves the guests attentively, and some nights she knows most of the guests by name. On Sundays and Mondays when the restaurant is closed, she goes in to clean or do paperwork.

The interior of Jackson Grill is divided into the bar room in the front and the dining room in the back. The decor is minimal; other than the brightly lit bar back and liquor shelves, the rest of the place is dimly lit. Candles and pendant lights add a soft glow and creates a relaxing and intimate ambiance. A display of famous signatures on long rectangular blackboards framed in gold hang on the walls in the front room. The signatures are of past baseball and football players and local celebrities. They were collected and displayed at Chef Jimmy’s father Ray’s restaurant. Located on Bluemound and 51st Street, it was a fly ball away from the old County Stadium and a popular hangout for Brewers and Packers players after a game. A few of the guys with signatures on the wall are regulars at Jackson Grill.

The menu is excellent. The crab bisque is one of the best I have ever had. There are five dressing options for the salad. The Nueske’s hot bacon dressing was Heidi’s old family recipe and is uniquely delicious, with ingredients like a can of Coke and Nueske’s bacon among others in the recipe. It’s a shame that you can’t get the prime rib any other day except Saturday because it truly is the best cut of steak, in my opinion, and they do it right. Chef Jimmy makes au jus from each piece of steak. Steak sauce will not cross your mind after the first bite. All the rest of the entrées are great as well. Choose your preference. You won’t be disappointed.

After the last dish is served, Chef Jimmy comes out from the kitchen to visit each table, greet each guest and catch up with regulars. He and I exchanged stories about growing up in family restaurants. He told me a story about how he ended up being placed in a room on Frank Sinatra’s private floor in a Las Vegas hotel and was treated like a member of the Chairman’s entourage.

Chef Jimmy and Heidi work tirelessly to provide each and every guest the best experience possible. They said the joy of being able to do what they want at their own restaurant outweighs any hardship and long hours that comes with it. What they wanted to do from the start was to give people great food in a relaxing and welcoming environment. In a sense, that is the supper club spirit.

Jackson Grill opens 5:00-9:00 Tuesday-Thursday, and 5:00-10:00 Friday-Saturday; closed Sundays and Mondays. For more information or to make a reservation, call 262-552-8008.

For Part Two of Inside Wisconsin Supper Clubs at the Hobnob, click here.

Southeastern Wisconsin Supper Clubs:

Jackson Grill
3736 W. Mitchell St., Milwaukee
(414) 384-7384

Dobie’s
4136 S. Kinnickinnic Ave., St. Francis
(414) 744-9064

Joey Gerard’s
5601 Broad Street, Greendale
(414) 858-1900

11120 N. Cedarburg Rd, Mequon
(262) 518-5500

HobNob
277 S. Sheridan Road, Racine
(262) 552-8008

The Old Fashioned
23 North Pinckney Street #1, Madison
(608) 310-4545

Toby’s Supper Club
3717 South Dutch Mill Road, Madison
(608) 222-6913

Stagecoach Inn
11946 North State Road 26, Fort Atkinson
(608) 868-3850

Buckhorn
11802 North Charley Bluff Road, Milton
(608) 868-2653

Elias Inn Supper Club, 
200 North 2nd Street Watertown ‪
(920) 261-6262