Chicago Sandwich Canon: The South Side’s Jim Shoe

There is a good chance, if you are a person interested in food who has somehow stumbled across our humble sandwich blog, that you are already familiar with at least the broader aspects of the Chicago food canon. You probably know about deep dish pizza, though you may or may not be aware that is is only 1 of Chicago’s several native pizza styles, and not the most commonly consumed. You almost certainly have heard of the Chicago-style dragged-through-the-garden hot dog, whether you know of the more stripped-down “Depression Dog” or the Maxwell Street sub genres. The phrase “Italian beef sandwich” has likely entered your lexicon at some point. The more advanced student may also display knowledge of the jibarito or even the breaded steak sandwich.

There are deeper recesses of foodie lore on the South Side though, a collection of sandwiches that are not as widely known outside of their local devotees. The Mother-In-Law, a tamale-in-a-bun covered in chili and Chicago-style hot dog toppings, has gotten some press but has always been difficult to find. There’s the Freddy, a nearly-extinct sandwich consisting of an Italian sausage patty in a French roll with red sauce, sweet peppers and cheese, sold at Calabria Imports in Beverly and a few other Italian delis scattered throughout the south side and the south suburbs. Also maybe flying under some people’s radar is the Big Baby, a particular style of double cheeseburger with grilled onions sold mostly at Greek-owned fast-food establishments called “Nicky’s.” The sweet steak, a sort-of cheesesteak with tomatoes, sweet peppers, and plenty of a mild sweet barbecue-style sauce, and the less celebrated Chicago-style hoagy, a collection of turkey-based cold cuts (no pork) served with American cheese, onions, pickles, tomatoes, pepperoncini, and a vinaigrette-style “hoagy juice,” are also worthy entries in our local sandwich pantheon, both sold at the same, generally Black-owned hoagy houses throughout the south side and into the suburbs.

One of the more obscure among these, with recent but still murky origins, is the Jim Shoe. The Jim Shoe sandwich–sometimes spelled Gym Shoe or Jim Shoo–is a monstrosity of a sub sandwich that is mostly found on Chicago’s South Side. A good Jim Shoe is… well it’s a mess, frankly. The sub combines corned beef (often referenced as “corn beef” on sandwich shop menus that serve it), roast beef, and gyro (generally pronounced “GUY-ro” at these establishments) meat, with onions, mustard, “gyro sauce” (not to be confused with tzatziki–the sauce may range from something quite close to tzatziki toward something more akin to Ranch dressing), cheese, and sometimes giardiniera, served with lettuce and tomato in a hoagie roll.

If that sounds like a lot, that is only because it is a lot. It’s a lot of stuff to put into a sandwich. The more restrained versions offer cold slices of the various meats, with a somewhat proportionate presence of lettuce, tomato, and onion, mustard and gyro sauce. If you have ever had cold gyro meat, you can imagine that this approach is not a very good one. I recently had a cold sliced version of the Jim Shoe from Alpha Gyros in Harvey, the nearest place to my house that serves a Jim Shoe, as far as I can tell.

This was not a very good sandwich, though the fries were decent, and Alpha Gyros correctly offered them with mild sauce on. Maybe I am just good at picking the right places, but in my experience the cold sliced version of the Jim Shoe is not what I usually find offered. More commonly, the sandwich maker will toss the corn beef, roast beef, and gyro meat onto a griddle along with some onions and possibly giardiniera, and chop them all up together into a hot, meaty mess. This version from Super Sub at 1050 N. Ashland featured chopped, griddled meats without giardiniera, a well-toasted roll, with copious amounts of gyro sauce both below and above the meats, but left the cheese unmelted, cold slices situated between the meats and the sauce.

Super Sub is a bit of an anomaly as it is located on the North side–that is, on the near West side technically but north of Madison, anyway. In other ways it matches the pattern of the type of place selling Jim Shoes to some extent, as does Sun Submarine at 5542 W. North Avenue on the far West side. Both are owned by South Asian immigrants, featuring extensive menus focusing on sub sandwiches and gyros, with minimal if any pork products available. (I note that the online menu for Super Submarine lists a ham sandwich but the ham in question is likely Turkey Ham. Sun Submarine apparently offers a bacon cheeseburger, which I’ll have to see to believe.) Both are, and were in pre-Covid times, primarily carryout restaurants. Sun Submarine’s Jim Shoe was made similarly to Super Submarine’s; a chopped and griddled combination of meats, this time containing giardiniera (often simply called “hot peppers” at Chicago sandwich stands), with a thick layer of what might be mayonnaise along with the cheese, a scant presence of tomato and lettuce, and a gyro sauce that has more in common with Ranch dressing than with tzatziki sauce.

There is generally also a shop or two on Howard street, along the city’s North border with suburban Evanston, that offers a Jim Shoe. I did not make it up that far north this month. For the most part, Jim Shoe shops are clustered on the south side around predominantly Black neighborhoods, like Best Southtown Gyro (formerly Southtown Subs) at 240 E. 35th St. in the South Side neighborhood Bronzeville. I had been requesting my Jim Shoes unwrapped, to try and get better photos of them, but I forgot to ask for that at Southtown so the Jim Shoe came tightly wrapped in foil, nestled inside a styrofoam clamshell alongside an order of fries with mild sauce.

It was the best Jim Shoe I’d had so far this month. The Southtown Jim Shoe came without giardiniera–some places don’t count that as part of “everything” but will still generally add it if you ask for “hot peppers”–but the cheese was shredded and mixed in with the meats on the griddle rather than added as cold slices to the sandwich after the fact, and the whole package was improved as a result. I began to suspect that there might be an inverse relationship between the flavor of a Jim Shoe and its photo-readiness.

I emailed Peter Engler, an old friend and author of a 2013 article on LTHForum that I still consider the definitive document on the Jim Shoe, to ask his secret for getting such good photos of them. He did not go so far as to support my theory that the tastier a Gym Shoe got, the uglier it was likely to be. He did, however, suggest that getting them unwrapped as I’d been doing might be a mistake. “Maybe a few minutes of steaming in the wrapper is important to meld flavors (certainly the case with Big Babies)?” he speculated. “At least that’s how most Shoes are consumed.”

He also suggested another spot to try, his current favorite Jim Shoe at Super Sub & Gyros at 2810 W. Marquette Road in the Marquette Park neighborhood of Chicago. Super Sub not only offered the Jim Shoe sandwich, but also a Jim Shoe Super Taco with nearly the same collection of sandwich fillings served wrapped inside a well-grilled pita. While there, Mindy also spotted some small packages of taffy grapes visible inside a cooler behind the ubiquitous bulletproof-glass window that most of these shops have, and had to try them. We took our treasures across the street to picnic on the steps at the base of an Art Deco monument to the pilots of the Lituanica.

The Super Sub & Gyro Jim Shoe is an exceptional version, well-griddled, balanced (relatively speaking), offering multiple bites of the “sweet spot,” something I had convinced myself must exist in each Jim Shoe, a moment where the ratios of each ingredient are in perfect harmony, the salty corn beef and the savory roast beef, the fat and garlic and pepper of the gyro meat, the enveloping cheese, the pungent bite of the mustard cutting through all of the above, the fire of the giardiniera and the cooling yogurt and cucumber of the gyro sauce, all perfectly balanced in a single bite that makes the entire sandwich worthwhile. I have experienced these moments while eating many a Jim Shoe, but maybe never quite as many as with that particular example from Super Sub. I found the Super Taco less rewarding, as the format made eating it an even sloppier prospect than the sandwich, but I was interested to see what is clearly a slice of melted yellow American cheese tucked inside. The grapes were juicy and cold and refreshing and tasted very much like a taffy apple in grape form.

We will back to Super Sub & Gyros for sure. But after that exemplary version it was time to reset my baseline by returning to the spot that I had always considered to have the best Jim Shoe, the spot that I drive out of my way to visit when the rare urge for a Jim Shoe overtakes me, the spot where I take foodie friends visiting from out-of-town when I want to demonstrate a real Chicago experience to them, a spot that is shouted out time and time again, Stony Sub at 8440 S. Stony Island in Avalon Park.

Stony’s shoe is an exemplar of the over-the-top nature of the sandwich in general. Bursting with griddled bits of meats and giardiniera, tightly glued together with melted cheese, lightly coated with paper-thin shreds of lettuce and slices of tomato and minimally dressed with hints of gyro sauce, the Stony Sub Jim Shoe may be the most meat-centric Jim Shoe of them all. The Regular Jim Shoe is more than one person should eat–there is a King version available as well, twice as large. I’ve split the King between 4 people comfortably. The Jim Shoe is wrapped in paper and then slipped into a narrow paper sack. That paper sack gets put into a larger paper sack along with the order of fries that comes with every Jim Shoe. If you order lemon pepper or mild sauce or another of the available wet or dry toppings for your fries, that topping will be added right on top of the open paper sleeve of fries. It is just the way things are done here. The Jim Shoe also comes with “Can Pop,” your choice of whatever flavors of generic Vess brand soft drink are in the cooler that day. Pineapple is a favorite. Don’t let them tell you the Fruit Punch tastes like strawberry; it doesn’t, it tastes like bubble gum like every other Fruit Punch flavored pop does.

Stony’s Jim Shoe is not a sandwich, it’s an institution, an undertaking, a rite of passage. The relative lack of mustard makes hitting the “sweet spot” less likely, but every bite is delicious nonetheless. A Jim Shoe at Stony Sub is generally the last meal you’ll need that day, possibly that weekend. So wouldn’t you know, that same afternoon we went out and found something even more over-the-top.

Another of the Chicago style of eateries that are spread across the south suburbs–which I did not mention earlier since “cheesesteaks” are already claimed by another city–are the “Steak and Lemonade” shops typified by Baba’s Famous Steak & Lemonade, a loosely-franchised collection of restaurants offering cheesesteak sandwiches–different from the Philadelphia version as they use green peppers and often mushrooms in addition to onions, are more likely to use some version of provolone than Cheez Whiz, and aren’t ashamed to add accoutrements such as mayonnaise, lettuce, and tomato. The Lemonades offered by these restaurants are large, sugary-sweet frozen drinks similar to an Italian Ice. Many of the Baba’s locations and their knockoffs offer something called a “crispy cheesesteak,” consisting of the steak, onion, green pepper, mushrooms, and cheese filling of one of their sandwiches wrapped in a flour tortilla and deep-fried.

A few of the Baba’s Famous Steak & Lemonade locations–notably the location in Aurora as noted by this Tribune article, and the location in Bolingbrook which we visited–also offer a crispy Jim Shoe. This absolutely immense bastard of a chimichanga–jimshoechanga? Doesn’t quite roll off the tongue, does it?–has to be served in a catering tray due to the sheer mass of the thing. If the Jim Shoe is so named because of its size and shape being similar to athletic footwear–I don’t know that that’s the case, but it’s certainly one theory–this thing could be called a Clown Shoe.

The crispy Jim Shoe at this Baba’s location is served on a bed of fries, with tzatziki, lettuce, tomatoes, pickles and such on the side, separated from the hot ingredients by an aluminum foil divider. If the King Shoe at Stony Sub could feed four people, this could feed… well, four really hungry people, let’s say. I was only able to eat part of one half of the thing. It is a less successful deep-fried Frankenstein than some other similar dishes like the aforementioned crispy cheesesteak, or Detroit’s corned beef egg roll. Rather than giardiniera, the filling appears to include sweet peppers, which I feel must be a mistake with the Jim Shoe. Additionally, rather than integrating a meltier cheese right into the meat filling, the tortilla(s) were lined on the inside with a stretchier cheese like mozzarella. It may be that this was intended to protect the tortilla wrapper from the meat juices but the end result was a dryer-seeming filling.

Soon after this expedition, I was able to convince Peter Engler, the scholar of South Side culinary oddities who’d introduced the Jim Shoe to a larger audience with his article back in 2013, to come out and join us for an afternoon of Jim Shoe hunting. Since we’d already hit many of the prime spots, Peter took us to the place where he’d first tried a Jim Shoe sandwich decades before–in fact so long ago that he wasn’t quite sure how well he’d liked the sandwich at the time–Jeffery Chicken & Sub on 71st Street in South Shore.

Jeffery had in fact recently undergone a bit of a face-lift, having moved from a spot next door–now a small grocery market–to a bright, more newly-built brick storefront. As with many fast-food establishments, and in fact most of the places serving Jim Shoes, the menu is displayed right on the walls of the restaurant, though this particular menu was a more polished version than many. In fact, the entire shop was sparklingly clean. Peter immediately engaged the proprietor in conversation in a way that I have never consistently been able to accomplish, and learned the history of this establishment as well as several others owned by the gentleman’s family, including a shop in Milwaukee that Peter had mentioned in his article.

Since 2013, Peter’s research into the sandwich has only intensified, and it seems like another, more ambitious project may be in the works. But in the meantime he has been working on the Chicago FoodCultura Clarion, a collaborative art and food publication offered with some editions of Chicago’s alt-weekly Reader for which he shares editing duties with another friend of the site, Eric May. He also gives the occasional talk on the South Side food lexicon for a linguistics class at the University of Chicago. And he knows this part of town. When we left Jeffery sub with our Jim Shoe–a sandwich with serious heft, even larger, thicker, and heavier than the Stony Sub version–he immediately suggested picnicking at the nearby South Shore Cultural Center.

While Peter and I planned to share a Jim Shoe–or at least take a few bites each of half of a Jim Shoe before moving on to try another spot–Mindy had different ideas, selecting an order of Dorito nachos from Jeffery’s extensive menu.

This led to a digression in which we spent a good portion of the ensuing afternoon talking about Dorilocos, a Mexican street food snack consisting of a bag of Doritos slit open and topped with any number of things, often including shredded cabbage, pico de gallo, cucumber, tamarind sauce, lime juice, candied peanuts, cueritos (pickled pork rinds), hot sauce, sour cream, avocado, even gummi bears! It’s the kind of conversation you only have with a foodie like Peter–and it led to me trying Dorilocos for the first time, a story for another occasion, another website perhaps. We did, though, eventually get into that Jim Shoe sandwich.

It was a stellar version, finely chopped and well-crisped on the griddle, devoid of giardiniera but of course that could be added upon request, with a solid presence of all the remaining requisites–mustard, gyro sauce, cheese. With giardiniera added it could be the equal of Stony Sub, perhaps, a real find both for the quality of the sandwich and for the boost to Peter’s research.

On our way out of the South Shore Cultural Center, we stopped by a nearby spot called Hoagy House to test a theory Peter about the separation maintained between the types of places that sell hoagies and sweet steaks from the types of places that sell Jim Shoes.

The theory did not pan out. But as Peter noted in his 2013 article, the sandwich has been spreading rapidly and that barrier was bound to be crossed eventually. Though we did not get a Jim Shoe here, we did note and ask about the sandwich listed directly below it on their menu, something called Peppermint Steak. This is apparently a Jim Shoe variant using Italian beef instead of the more standard roast beef.

Why is it called Peppermint Steak? That is another mystery for another day.

From there we made our way south, past the corner of 71st and Stony Island where well-dressed young men from the Nation of Islam sell bean pies, past Stony Sub, past the (sadly) now-closed Kenwood Liquors where we talked Daniel and Katy into buying a bottle of Jeppson’s Malört (a bottle that they ended up liking more than anticipated), down to Roseland’s New Taste of Chicago at the corner of 111th and Michigan, just up the street from the city’s best donut shop. Our source at Jeffery had said that he thought the sandwich might have originated at a shop in this area, a theory that Peter had heard floated previously, and we thought we’d give it a shot.

New Taste of Chicago was chaos. Nobody was going to learn anything there that day. As we entered, there was a steady stream of partially-masked kids moving in and out and around the ordering area, returning their food orders in batches to the bulletproof glass lazy susan at the window and asking for mild sauce. We were eventually able to get to the front and order a Jim Shoe (but no ice cream that day, as the scoop was apparently broken), not really tempted by New Taste of Chicago’s more-extravagant “Pack Shoes” version which added chicken to the already extensive list of meats in the sandwich. After making our order and being told it would take 10 minutes, we returned to the car to wait. Ten minutes later I walked back into the store, having completely somehow missed the police car parked just outside, to find the cashier in a verbal dispute over a refund with an angry young lady and a uniformed audience. Not our business, so we took a walk and returned a few minutes later to find an UberEats driver angry that her order wasn’t ready. In a rare calmer moment, the cashier told us it was frequently like this at New Taste. In any case, we were able to get our Jim Shoe and take it around the corner to some bleachers at Palmer Park.

We could only laugh in amazement at the gargantuan chunks of gyro meat we found in this sandwich. I am not one who believes that gyros should be sliced paper thin, but I like the juicy bits and the crispy bits to be in balance and this took things too far in the other direction. We picked at it a bit, and even ventured a few bites–the bread roll was marvelously toasted, which added a lot more flavor than you might think. This was easily the biggest of the Jim Shoe sandwiches I’d tried this month, but even with a sandwich like this, where any sense of moderation or balance must be discarded before even ordering it, bigger does not mean better. This was a delicious piece of bread stuffed with thick slabs of gyro meat, some scattered wisps of corned beef and roast beef, and not much else. It wasn’t really possible to eat it as a sandwich, and though there were some good things about it, overall it was a disappointment.

There’s more to the story of the Jim Shoe, of that I’m sure. I’m also relatively certain that if anyone will learn its truth, the origin that has been so difficult to track down, it will be Peter Engler. I can’t wait to see what else he will be publishing about it, or the next unique South Side culinary offering he helps bring to a wider audience. I hope one day soon I can talk him into going on another sandwich ride with me. In the meantime, if you’d like to hear what he has to say about the culinary lexicon of Chicago’s south side, your best bet may be to enroll at the University of Chicago and major in Linguistics. Hyde Park seems like a pretty great little neighborhood, and if Peter is any indication, it’s an excellent launching spot for exploring the South Side.