Frankie’s Pub in Sheboygan: A True Boss’ Hideout

Frankie's Pub in Sheboygan, Wisconsin

Well, doesn’t that look exciting.

This is Frankie’s Pub and Grill in Sheboygan. Gaze upon its earthy-toned siding, its plain signage, and its majestic … shape? Why are we even still looking at this?

That’s exactly what they want to you think.

You know this area’s history, right? This is where Chicago’s gangsters ran off to when the big city got hot. Maybe they brought a pal from a rival gang. Maybe they gave him a round of applause and helped him into Lake Michigan. What I’m saying is, should he or she need to hide out, this … shape … looks exactly like what a kingpin would sneak away into. Hell, it’s virtually hiding in its own photograph.

Step inside and, sure enough, there’s (mannequin) Al Capone in the entry. Clean white suit, big ol’ cigar in his hand. Past him, a star-studded and shady-rooted crew forms an audience on the walls: Sinatra, Jimmy Dean, Monroe, Hepburn, Scarface. It makes perfect sense.

What’s everyone hiding out here for? This:

A cheeseburger challenge at a pub and restaurant in Sheboygan, Wisconsin

The boss would like to see you now.

The Basics: You can find Frankie’s on the Internet here and find directions to Frankie’s here. IF you’re wondering, here was our route home from Door County had we not driven to Frankie’s. We went this way instead, and we’ll do it again if given the chance.

If you want bright, sit next to a window; on a sunny day, your table could be a tanning bed. The rest of the place, oddly enough, was unusually dusky for mid-day standards. Maybe it’s the window placement, maybe something else. A buzzcut man hustled over to us not long after we sat. We didn’t need much time with the menus.

What we’ll do is,” said the tender, stroking his goatee the way I would, “since the challenge takes up the entire grill, we’ll bring the fries and the other burger out first.” I just about had an aneurysm when the “small” burger came out.

In less than 30 minutes, the spread was complete.

You know what you’re getting when “Challenge” is in the name, but is the one of the left not the biggest “regular” cheeseburger you’ve ever seen? Like, that’s their Quarter Pounder essentially.

Frankie’s Challenge, bottom to top: Bun, pickles, onion, bacon, burger, cheese, burger, cheese, bacon, bun, onions, burger, cheese, burger, cheese, bacon, lettuce, tomato, bun. A knife was plunged into its hat, but wasn’t long enough to penetrate its whole body. After an extended photo shoot, I readied my jaw, pressed out some handles, and started the advance.

The squeeze burst open pockets of grease and tomato juices, that immediately made their way down to the bottom bun and rendered it a wet paper towel. The top bun fractured. My first bite was a nibble of bottom bun, but my next bite gave me a starting point (and a nostril full of cheese and onion bits). I flipped the burger on its head and began working the top.

Across the bar, a woman took pictures — not an employee, not someone I knew, just a woman who’d been watching TV and decided this was more interesting. Is that weird? I don’t think so … but is it weird that being photographed while eating isn’t weird to me anymore?

The Frankie’s challenge goes like this: Finish it in 45 minutes, it’s free and you get a prize. I made good headway in a short amount of time, but no prize was worth the next five hours in a car with this whole thing in my stomach. I called for the doggy bag barely a third of the way in.

A man in a pink T-shirt attempting a cheeseburger challenge at a pub and restaurant in Sheboygan, Wisconsin

About that doggy bag: Do you think they make one big enough for this? Nope. My “box” was two paper plates and half a roll of saran wrap.

Challenge burgers are worth it, even if you wimp out. Forget the week of meals I’m getting from this: I’d pay $30 (THIRTY BUCKS, only!) just to hold this. Our total bill (two “regular” burgers — or whatever passes for regular around here — fries, and two beers) ran us $64 lighter. That’s easy.

Frankie’s Pub is easy, too; if you’re not in the know, it’s easy to miss. It’s easy to miss on your map, it’s easy to miss in its own neighborhood (seriously, only six or seven people there on a Sunday?!).

Learn the handshake, though, and it’s hard to not want to come back to. Service was good; the beer selection was unexpectedly diverse; and, even if you shrunk these down to a normal size, the burgers tasted fantastic. I would eat one of these if it was only eight ounces.

Good thing I don’t have to. Thanks, boss!