Skippy's

"If you need some proof that Staten Island is a small town, head to Skippy’s, a legendary hot dog truck currently parked on Hylan Boulevard. Open since 1962, the line is always full of people who went to junior high school with each other—and also the proprietress, Dawn, who inherited the truck from her parents, and will call you “sweetie” a minimum of three times, but probably more like five. Order anything that involves Dawn’s bright red, homemade chili—we like the Wally Dog, with cheese, chili, and sauerkraut—and then sit on a bench, and drink a Dr. Brown’s black cherry soda." - willa moore

"Don’t come to Skippy’s expecting dry-aged, artisanal hot dogs—the dog is Sabrett, and the cooking method is boil. Do come to this legendary Staten Island hot dog truck to eat a Wally Dog, which costs $3.25 and has sauerkraut, cheese sauce, and bright red chili on it. That chili is homemade by Dawn, the woman in charge—she inherited the business from her parents, and even though she runs a tight one-woman ship, she’lll take the time to call you “sweetie” at least three times. Order a few dogs and a Dr. Brown’s black cherry soda, and then sit on a bench next to someone who comes here almost every day on their lunch break and burps liberally—feel free to join." - bryan kim, willa moore, sonal shah, molly fitzpatrick

"A Staten Island institution since 1962, Skippy’s is a hot dog truck run by a woman named Dawn, who will call you “sweetie” a minimum of three times, but probably more like five. There’s always a lunch break line, full of people who went to junior high school with Dawn and now come here almost every day and order four Wally Dogs and a Dr. Brown’s black cherry soda. Don’t come to Skippy’s expecting artisanal meat—the dogs are Sabrett, and the cooking method is boil. Do come expecting bright red, homemade chili, small-town charm, and prices that hover around $3. Skippy’s is currently parked on Hylan Boulevard next to Last Chance Pond park, which is a pretty pleasant backdrop for a cheese dog. The truck is open until 3pm, but things sell out—especially the chili—so plan accordingly. photo credit: Willa Moore Food Rundown Hot Dog If it wasn't already clear, you’re not here for a plain dog. Don’t waste stomach space—the toppings are why you’re here. And also the people-watching. Chili Cheese Dog Dawn used to sell her homemade chili by the cup, but then it started selling out too fast, so now you can only get it on-dog. Sometimes when you ask very, very nicely, she might sell you a cup, but if you didn’t go to preschool with her, this might not work. If it doesn’t, just get a lot of chili-based hot dogs, because the chili-to-bun-to-hot-dog ratio is about 1:1:1. Wally Dog A chili-cheese dog, but with sauerkraut. Otherwise known as a perfect specimen, especially if you’re into fermented cabbage." - Willa Moore