After eating his 1,000th cheesesteak, Jim Pappas found himself at a crossroads. There had been milestones and media attention along what he called his Cheesesteak Adventure — a self-assigned mission to consume and rate 1,000 cheesesteaks across the region — with coverage of his 275th, 500th, 999th, and final conquests. At one point, there was even a proposal for a TV show.
It all lined up with what Pappas believed he had been working towards: a late-life career change.
But when the adventure ended in early 2022, “nothing happened,” the 61-year-old told Billy Penn.
A romantic relationship that had inspired his four-year challenge fell apart around cheesesteak #980, and planned collaborations to capitalize on his moment of fame quickly fizzled out.
For a while, Pappas plowed on, finding new spots to hit up between his rideshare gigs, but his heart was no longer in it; his cheesesteak intake dropping to an unprecedented low: one every three or four days.
“I was wondering if it was all a waste of time,” Pappas said. “And thinking of all the mistakes I made.”
After a period of self-reflection, he’s now back on the scene, reenergized and refocused. There’s a clothing line he’s been working on since late last year, as well as Cheesesteak Stories, an interview podcast planned to launch May 16—six years to the day since the start of his adventure.
Billy Penn joined up with Pappas for a three-stop cheesesteak crawl to discuss his future plans and past experiences.
Cheesesteak #1141, Lorenzo’s Italian Market
On a busy Italian Market corner Pappas stands out, in a white shirt patterned with anthropomorphic cheesesteaks matching the ones on his loafers, where the enlarged “I’m Cheesy!” speech bubbles become more legible. Underneath the open button-down is the same t-shirt worn in most of his video reviews, with a now faded drawing of Pappas driving a cheesesteak mobile.
Lorenzo’s on 9th and Christian won first place in last year’s Italian Market Festival cheesesteak competition, but had so far been overlooked by Pappas. “Looks like we’ve got a chopped-ripped thing going on here,” he said, poking at the meat in his half of a roll.
For every cheesesteak he’s had, Pappas assigns a score out of 100, with points divided across five categories: roll, meat, cheese, extras, and experience, like setting and bang for buck. Mushrooms, he said, are a good way to gauge the overall effort put into a cheesesteak—straight from the tin is never a good sign.
Ratings are determined at home while reviewing the on-site footage he’s filmed; the videos are uploaded to his YouTube channel, the scores to a detailed spreadsheet.
He suspects Lorenzo’s will land somewhere in the 80’s. The lowest he’s ever given was a 54.
He’s often gotten grief for being too lenient with his scores. “People will go, ‘you should trash that place, that was horrible,’” he said. “But, you know, nobody’s out there trying to make a bad cheesesteak.”
There have been harsher criticisms throughout, from accusations of selling out, which he finds odd (Pappas admits to getting paid only once by a business owner, for a request to drive out to Harrisburg), to crueler, more personal attacks. It’s particularly stressful during March Cheesesteak Madness—the college basketball-style tournament Pappas organizes. He recently hosted the tournament for the fourth year, and does it increasingly out of a sense of obligation to his partners.
“It’s just nonstop ‘you’re an idiot,’ ‘how did you miss this place,’ ‘it’s rigged,’ ‘who’s paying you off,” he said. “It’s like, this is supposed to be fun.”
Much of the initial appeal, Pappas said, was in meeting new people and supporting (mostly) small businesses, but the project has taken on more meaning as he’s grown older.
“People my age are in one of three categories: you’re either in or had a great career, and [have] a lot of money,” he said. “Or you’re stuck in a job you need to keep because you gotta pay the bills.”
“Or you’re worried. You haven’t had a great career and you’re worried the whole world has passed you by and there’s this new technology you’ll never understand.”
Cheesesteak #1142, Shay’s Steaks
At Shay’s the steak selections are New York strip ($19), prime rib ($20), filet mignon ($28), and American wagyu ($32). Pappas opts for the New York strip, with black garlic and truffle seasoning, and mushrooms. The mushrooms are thoroughly grilled (“could be a little bigger”), but the steak elicits an immediate “holy mackerel,” followed by another a few bites later.
It’s a new space, launched earlier this year by owner Jackee DiClaudio, and inspired by her husband Scott’s memories of working at his parents’ South Philly luncheonette.
After catching an eyeful of Pappas’ shirt, Scott DiClaudio comes over to discuss the quality of his steaks, before leading the way into his kitchen for visual confirmation. He points out the lack of a freezer, “nothing here is frozen,” he repeats. Available in a variety of seasonings, the steak sandwiches are each 8 oz, with the meat cut to order.
Back at the table, Pappas points to a framed portrait of DiClaudio’s parents (Shay’s is named after Scott’s mother), and remarks on the resemblance between father and son. Throughout the afternoon, the topic of fathers had drifted in and out of conversation, coming up later on the drive to the third destination.
Pappas grew up in Swarthmore, in what he joked was the only divorced family in town. “My dad was supposed to show up Saturdays—he wasn’t real good at it.”
When he did appear, it always meant a trip to Claymont Steak Shop. “It was like a double Pavlovian dog,” Pappas recalled, “he showed up and we’re gonna get cheesesteaks.”
Claymont cheesesteaks served as the basis for a later, pivotal relationship for Pappas—one that came after stepping away from a 25-year career in finance, launching a cleaning service with his wife that ended their marriage, moving back to Wilmington nearer his family, and surviving a debilitating car accident. His new partner, who he met through a rideshare passenger, had grown up around the corner from Claymont and still knew the number by heart.
“She was the face that launched a thousand cheesesteaks,” Pappas said. On an early date, the couple grabbed sodas from Wawa, Fireballs from a liquor store, and headed to Claymont, their conversation leading to plans for what would become Pappas’ Cheesesteak Adventure.
Now, he said, “I’m still doing rideshare, still eating cheesesteaks. But she’s long gone.”
Cheesesteak #1143, Hibiscus Cafe
Out of the thousand-plus cheesesteaks he’s ranked, Pappas estimates only six or seven have been vegan. A few bites in, he puts Hibiscus Cafe’s at the top of the brief list.
He expects he’ll receive some comments like he’s gotten in the past, condemning the concept of vegan cheesesteaks. But reviewing traditional spots, Pappas said, isn’t necessarily a safer bet. He recalled receiving repeat messages from one individual outraged with the “low” rating given to John’s Roast Pork: an 80.
“So, I asked him, ‘well, why do you like it so much?’ And he started talking about these memories he had of standing in line there as a kid, holding his dad’s hand, and how it was the first thing they did alone together.” The two ended up reminiscing about dads and cheesesteaks for fifteen minutes.
“That’s the thing with any of these cheesesteak stories,” Pappas said. “It’s never about the cheesesteaks.”
That’s the idea, and title, of the podcast Pappas has been planning for a while. He’s envisioning a twice-a-week, half-hour talk show format where the focus will be turned on guests; from friends who’ve appeared on his previous video reviews to anyone who reaches out with a story to share.
“That’s what’s gonna turn this,” he said of the post 1K stretch of his ongoing Cheesesteak Adventure, “into something fun.”
Looking back, Pappas admits he’s made a few bad decisions (“when a casting agent calls you,” he advises, “don’t think your idea is better than her idea”), but ultimately has no regrets for the path he’s on. Over the course of the afternoon, he repeats he’s lived a full life and that he’s particularly proud of his two daughters, both officers in the Naval Reserve, even though they often ask when he’ll get a “real job” again. A few of his friends, he said, have been slowly shifting to the same camp.
Pappas isn’t planning on joining them anytime soon.
“I do have a third act in me, and I really want it to be this.” Everything, he said, is constantly changing, “and if you can reinvent yourself, it’s a beautiful thing.”
For Pappas’ reviews of Lorenzo’s, Shay’s Steaks, and Hibiscus—and over 1,000 more cheesesteak spots—check out his YouTube channel. If you have a story to feature for his upcoming podcast, Pappas encourages you to reach out at (732) 228-3140 or @cheesesteakadventure on Instagram.
