The original Skyway Jacks opened in 1976. That was back when the old Skyway bridge was in service. Back then Jacks was located at the marina a mile or two north of the bridge. A couple of things may have contributed to Jacks move farther north to 34th street.
For one thing, the restaurant had to share limited parking with the marina. Also, when the bridge was struck by the freighter Capricorn and collapsed in 1980, the roadway was for local and construction traffic only. The replacement bridge was not opened until 1987.
Skyway Jack's Restaurant has been a favorite for breakfast and lunch for locals and tourists alike since 1976. Look for the Humpty Dumpty on the front lawn or the large rooster just outside the restaurant. Order a classic steak and eggs for breakfast or enjoy one of the $2.99 specials offered Monday through Friday from 5am til 8am. Lunch might include a fried flounder, a whole catfish or even chicken dumplings with lima beans and carrots.
I’m a sucker for places that dole out authentic ”road food” – the greasier the spoon, the better (especially at breakfast). So I couldn’t leave the greater Tampa/St. Petersburg area without visiting Skyway Jack’s, an institution near the Sunshine Skyway that’s been open since 1976.
The restaurant’s Southern kitsch vibe hits you as soon as you pull into the parking lot. The windows are decorated with Porky Pig-style cartoons and a monster rooster greets you at the door. Skyway Jack’s claims that it serves 500 breakfasts on a typical Sunday and goes through 2,500 eggs, 400 pounds of sausage, 45 pounds of bacon and 4,000 cups of coffee a week! Not bad for a place that only seats 90 people at a time.
Once inside, you’re greeted by waitresses in politically incorrect T-shirts and a ton of pig paraphenalia. The place attracts all kinds – we saw people arriving from church, as well as a guy in fisherman overalls. One guy told the waitress he was getting married later in the day!
The menu is scrawled in marker on whiteboards mounted on restaurant’s wall. You’ll find all the usual breakfast standards, plus several with military touches (owner Jack Thomas served in the Navy and was a former cook in the Indiana National Guard). Among the more colorful offerings:. SOS (s— on a shingle), basically creamy sausage gravy ladled over biscuits and served with tomatoes; Anchor’s Away consisting of baked beans, smoked sausage, and cornbread; and An Apple A Day – baked sliced apples with sausage and corn muffin. 
When your plate arrives, you will be a little overwhelmed with the sheer amount of food in front of you.
True to the decor, there’s a whole slew of pork options, including pork brains scrambled with eggs: If you’re a vegetarian and squeamish about pig being served up so many ways, you might want to think about another brunch spot (although there were plenty of veg options such as waffles, French toast and pancakes).
Take a drive down 34 Street South before the sun rises.  Turn at the rooster and Humpty Dumpty statues. Kill the engine, take note of the sign advertising $3.99 early morning breakfast specials and walk into the Skyway Jack’s. Pick a table – the sign reads, “Please Seat Yourself” – and slump into either a well-worn booth or chair.  Smell the meat sizzling on the stove as it is lumped into a Philadelphia scrapple with eggs.
Read the signs on the wall: “Grow your own dope, plant a man.” “This is not Burger King. You don’t get it your way. You take it my way or you don’t get the damn thing.” And then notice the uniform shirts the waitresses wear.  A black or white T-shirt that reads, “Delicious fried eggs at Skyway Jack’s” accompanied by two well-placed fried eggs on each woman’s chest.
There's quite a history to this very unusual-looking fast-food restaurant. When Skyway Jack, an old Navy cook, opened the restaurant 40-plus years ago, he dreamed of serving up good food at an affordable price. Today, that dream is a reality, and though Jack is no longer around, people keep coming back for the rib-stickin’ entrées and heaping portions. Most show up for a hearty breakfast. Biscuits and sausage gravy, blueberry and chocolate chip pancakes, country ham and scrapple, brains and eggs, and baked beans and smoked sausage are favorites. Lunch includes a six-ounce Jack burger and daily specials ranging from chicken and dumplings to pork, mashed potatoes, black-eyes peas and greens. All menu items are made from scratch, mostly from family recipes, and some have originated from customers who bring their favorites for the cook to try as a daily special. Packed with fabric, porcelain and paper pigs in all shapes and sizes, and with views ranging from 34th Street to the retention pond out back, if you wear anything more than sneakers and shorts, you’re bound to feel overdressed.