The 10 most Philly jobs, according to Philadelphians

Jul 26, 2023

Some Philadelphians are so hardworking they don’t just have side hustles, they’ve got front, back, and diagonal hustles, too. The person scooping your wooder ice by day may be the podcast host you listen to at night and the entrepreneur you buy knockoff T-shirts from outside the stadium.

As Labor Day approaches, I wanted to know what Philadelphians think are the most inherently Philly jobs. I posed my question on X (the platform formerly known as Twitter), and received more than 150 responses, with some definite clear winners.

Here, I present, in no particular order, an unofficial list of the 10 most Philly gigs, according to Philadelphians.

Selling soft pretzels — whether it’s outside the stadiums or in the median of Roosevelt Boulevard — was the clear winner for the most Philly job (extra points go to vendors who use a shopping cart and hand over their pretzels in brown paper bags).

A few decades ago, soft pretzel vendors were all over Philly, but their numbers dwindled drastically in the mid-’90s after NBC10 reporter Herb Denenberg released one of the most amazing and twisted exposés in the history of Philadelphia journalism. Using hidden cameras, he caught vendors spitting in their hands, throwing cigarettes butts in their products, and selling pretzels that had been picked at by birds. Salty over the report, city officials cracked down on the sellers.

While it might sound like one of the oldest professions in the book, pole greasing is actually one of the newer gigs in Philadelphia. The city didn’t begin greasing poles until the Phillies’ 2009 World Series run.

Crisco was used at first, but when that turned out to be ineffective at stopping fans from propelling up poles, the city switched to hydraulic fluid. That’s proven ineffective too, but the city workers charged with this Sisyphean task (usually police officers and Department of Streets employees) continue to coat the poles anyway, in the name of safety.

Until a fully Philly-fan-resistant coating is discovered, pole greasing will remain an important Philly job.

It takes a true Philadelphian — someone who’s kind but has a no-nonsense attitude — to navigate a 40-foot bus through our pothole-plagued streets while dealing with dozens of passengers, each with their own Philly attitude.

Some drivers are famous for their sense of humor, like Eric “Bus Driver Doo” Lilley, while others are known for their heroics, like Chris DeShields, who used his bus to scare off carjackers in January.

Increasingly though, SEPTA operators have become victims of verbal abuse and assaults, which has led to a shortage of drivers. The city and SEPTA need to step up and protect those who are called to this essential Philly profession, to keep it thriving.

Whether it’s stuffing hoagies at Fink’s or slinging cheesesteaks at Dalessandro’s, making these regional delicacies is one of the meatiest jobs in the City of Brotherly Grub.

In their roll as craftsmen and women, the steaks are high and those who whiz to the top by perfecting the perfect ratio of meat, bread, and toppings are considered gastronomical heroes (just don’t call their products heroes, or subs, or sandwiches, for that matter).

When it comes to jobs wit a healthy dose of Philly, oil admit, these workers rise to the top.

We hold these truths to be self-evident, that whether serving as a rebel or a redcoat, donning colonial garb in 90-degree weather and 100% humidity is a very Philly pursuit indeed.

Sure, other cities like Boston and Williamsburg have historical reenactors too, but ours have the very important job of telling tourists why Philadelphia is better than all those other places.

If you want to write your own ticket to one of the most Philly jobs in town, consider joining the Philadelphia Parking Authority.

It takes thick skin to walk the streets in a PPA uniform, and it takes a tough Philly attitude to be immune to the sob stories, elaborate excuses, and epically-strung-together expletives spoken by motorists who swear they were just coming back to feed the meter.

If you’d rather be loved than feared while doing your job, doughnut worry, being a Tastykake truck driver might be right up your alley.

Driving the iconic blue-and-white box trucks through the city to deliver Krimpets and Kandy Kakes to corner stores and supermarkets is one of the sweetest jobs in Philly.

Dating back to the days of the horse and carriage, Tastykake delivery drivers have been fueling Philly’s need for a quick sugar fix for more than a century. It’s not as easy as pie navigating Philly’s streets, but the smiles the truck brings to the faces of those it passes is the icing on the cake.

Within minutes of a Philly sports championship win, dozens of eager entrepreneurs descend upon the stadium complex parking lots and Philly streets, ready to sell knockoff T-shirts to mark the occasion.

Their voices boom, their sales pitches slap, and they move hundreds of Phillies and Eagles T-shirts while dealing with hordes of drunken sports fans, making this job one of the ultimate Philly hustles.

How do these vendors know in advance which games Philly will win? Have they mastered time travel or do they keep a copy of Biff’s sports almanac from Back to the Future Part II in their pockets? We may never know.

Whether it’s the security guards who protect Gritty (mainly from himself) or the driver who chauffeurs the Phanatic around in his hot dog cannon ATV, being a wingman to these beloved mascots is about as Philly as it gets.

Gritty’s guards not only keep unruly fans at bay, they also help Gritty (whom they refer to as “the package”) navigate crowds and tight spaces.

But when it comes to the best mascot-adjacent job, the person who gets to drive the Phanatic’s hot dog cannon around Citizens Bank Park is the real wiener here. Any Philadelphian would relish a job that allowed them to hang out with the Phanatic.

In a city of entrepreneurs, some make a name for themselves by leaning into one particular niche and becoming part of the city’s landscape and lore.

In Philly, there’s the Pickle Man, the Candy Lady, the Flier Guy, the Carrot Cake Man, Jelloman, and the Bubble Queen, just to name a few.

These folks have found a way to make a living doing what they love, and in the end, perhaps there’s no job more Philly than the one that lets you be exactly who you are.

Staff writer Matt Mullin contributed to this report.