In the aftermath of the 2008 financial crisis, Jim Pappas — a Delaware County native who used to work in financial services — was unsure of what would come next. After going through a divorce and receiving a Leukemia diagnosis, then leaving his career, Pappas was looking for a new, fulfilling way to spend his days. He decided to ask family and friends where their favorite cheesesteaks spots were, then go and try them. It was a simple, modest mission, rooted in curiosity for trying new things and meeting new people, and a way to to spend his time.
In 2018, Pappas started the Philadelphia Cheesesteak Adventure with a new friend, with the eventual goal of eating 1,000 cheesesteaks from 1,000 different restaurants. His modest pursuit of great sandwiches quickly grew into a dedicated, ravenous community of fans nationwide who followed along as he set out to eat 250, then 500, then 800 cheesesteaks in Pennsylvania, New Jersey, and Delaware. On January 13th, 2022 — four years since he started — Jim Pappas will eat his thousandth cheesesteak.
On a Saturday afternoon in December, Pappas enjoyed his 986th cheesesteak at Cook and Shaker, a corner spot between Fishtown and Kensington. Pappas is chatty and engaging, filled with endless stories about cheesesteaks, parenting, and life, politely taking pauses mid-conversation to snap shots of his cheesesteak before and during the meal. He was dressed to the nines in Philadelphia Cheesesteak Adventure swag, including a T-shirt with a fan-designed cartoon of Pappas himself driving a sandwich as a car.
“You know why Philadelphians love cheesesteaks?” Pappas asked. “It’s the memories attached. ‘It’s my dad’s favorite place. Back of mom’s station wagon before the big game.’”
It’s for this reason that Pappas has formed such a dedicated community. Philadelphia takes its cheesesteaks seriously, and its’ residents seem especially (and famously) sensitive to any ranking of “best” or “worst.” Perhaps it’s Pappas’s sense of humor, dedication, and unrelenting respect for the process that has turned him into one of the area’s most reputable sources on the matter.
With stakes as high as disrupting Philadelphians’ childhood nostalgia, creating a range of preferences is a tricky feat. But Pappas has devised, despite some occasional pushback, what feels like a foolproof system, one that has informed his studiously updated spreadsheet of visited cheesesteak spots.
On the sheet, Pappas scores his cheesesteaks according to five categories: roll, meat, cheese, extras, and overall experience. While each category is unique, Pappas says, “It all starts with the meat. I grew up in the suburbs, so our cheesesteaks were always chopped. I want the fried onions and the mushrooms on the grill with the meat. Let them all mix together.”
The cheese, then, should be melted on everything, chopped up with the meat, and placed into a roll with a “thin crust and bread that collapses.”
The obvious wild card of his ranking system is “Overall Experience,” a category riddled with subjectivity. This category tends to incite the most controversy.
It’s really just a way to capture the spirit of Pappas’s overall pursuit. The experience of a restaurant, its staff, a great beer, and all the edible standards — roll, meat, cheese — all stack up to his ultimate purpose: a cheesesteak adventure, one that is rooted in memories of friends, family, and Philadelphia.
In April 2019, Pappas hit his first major benchmark of 250 cheesesteaks and wrote a Best Of list that generated national attention and thousands of followers, providing enough momentum that he vowed to get to 500 before the end of that year.
As with all ambitious ventures, it can be tough to go at it alone, and midway through the 400s, the adventure almost stopped completely until one of Pappas’s friends insisted, “Let’s just get there.” They pushed on together.
Once he finally reached the staggering benchmark of 500 in January 2020, Pappas figured he might as well keep going.
One thousand cheesesteaks became an arbitrary finish line, but one that has kept the adventure alive. Fans made art. He sold merch. His follower count grew with fans nationwide. He eventually landed on an all-time favorite. With a score of 96 out of a 100, it’s the cheesesteak at Charlie’s Roast Pork on S. 3rd Street in Pennsport.
Finding a thousand unique spots for a cheesesteak has surprisingly never proved difficult. “They’re like deer,” Pappas explains. “They’re hiding in plain sight.”
High into the 800s he decided to start soliciting guest eaters to join him for the ride, a decision that resulted in over fifty guest meals and reinvigorated his energy to make it to four digits.
To celebrate reaching one thousand cheesesteaks, Pappas will hold a party at the West End Boat Club in Essington, where fans can watch Pappas reach his goal. Tickets to the event are available on Pappas’s website. Guests will receive a commemorative T-shirt and a cheesesteak buffet. It’s an opportunity to watch Pappas make history.
What happens after reaching 1,000? Pappas wants his community to decide and help guide him towards new options. He has no plans of quitting the cheesesteak journey anytime soon, but his ambitions are growing loftier. He’d like to expand his reach, to transform into the city’s go-to source for cheesesteak expertise.
For now, though, he’s happy with what he’s built and the people he’s met along the way — it’s been one hell of an adventure.