Every argument about the best deep dish pizza in Chicago eventually collides with a rude fact: the pan-pizza crown has a second claimant, and it lives in Detroit. New York, never one to sit out a food fight, has quietly become one of the best places in the country to referee it. Over the past few years the city's Detroit-style contenders — Emmy Squared in the East Village, Ace's Pizza in Williamsburg, and the square-slice powerhouse Mama's TOO! — have turned caramelized frico edges into a local religion. So instead of another ranked list, this is a bracket. Three head-to-head matchups, one winner per situation, and a final round where the best deep dish pizza in Chicago tradition takes on New York's crispy squares directly.
Karpo can settle tonight's matchup for you — ask which of these squares is closest, how the walk-in line looks, and what to order first, all without leaving iMessage.
Round 1: Emmy Squared vs Ace's Pizza
This is the marquee bout: the polished restaurant versus the neighborhood rec-room. Emmy Squared at 83 First Avenue is the sit-down experience — a proper menu, cocktails, the award-hoarding Le Big Matt burger, and pans of Detroit-style pizza with rectangular corners of caramelized cheese. It also just got a facelift: the East Village location reopened in March 2026 after a four-month renovation, with a new mural by Ian Sullivan watching over the dining room. The signature Colony pie — pepperoni, pickled jalapeños, a slick of honey — remains the single best argument for the sweet-heat school of pizza topping.
Ace's Pizza at 637 Driggs Avenue in Williamsburg counters with atmosphere and cheese science. Open since February 2021, it blends low-moisture mozzarella with Midwest brick cheese — the authentic Detroit move — and ladles the sauce on top before the final bake, so every square comes out with racing stripes and a shattering edge. The room is pure retro clubhouse: vinyl booths, kitschy art, and an N64 in the corner. Verdict: Emmy Squared for date night and groups who want a full menu; Ace's for a low-stakes hang where the pizza still punches above its rent. If you work in Midtown, note that Ace's also runs an outpost at Rockefeller Center for the lunch crowd.
Round 2: Ace's Pizza vs Mama's TOO!
Now the purist meets the mad scientist. Ace's plays Detroit straight: brick cheese, blue steel pans, restrained topping logic. Mama's TOO! — the tiny Upper West Side shop that has been collecting best-slice-in-the-city votes since 2017, with a West Village sequel at Bleecker and Christopher — refuses to pick a lane. Its hulking squares splice Sicilian, Detroit, and Roman DNA into something entirely its own, then pile on vodka sauce, whipped ricotta, or calabrian chili oil until the slice needs two hands and a plan.
The formats differ too, and that decides the round. Ace's is a sit-down-and-stay spot with beer and a jukebox energy; Mama's TOO! is a counter operation where the line moves fast and the slices travel. Verdict: Mama's TOO! wins for the solo eater who wants one perfect square in fifteen minutes; Ace's wins for anyone staying a while. Splitting hairs on crust alone, Ace's edge is crispier, Mama's crumb is airier — order the corner piece at both and run your own tiebreaker.
Round 3: Detroit squares vs Chicago deep dish
The cross-city final. Chicago's pie is a casserole in the best sense — deep, sauce-on-top, a knife-and-fork commitment that takes 30-plus minutes in the oven. Detroit's is faster, lighter underneath, and built around that frico halo where cheese caramelizes against the steel pan. Searching the best deep dish pizza in Chicago will always return Lou Malnati's and Pequod's, and no New York square is trying to impersonate them. But on a weeknight, when you want pan-pizza decadence without scheduling your evening around a bake time, the Detroit square is the pragmatic winner — and New York's versions above are as good as it gets east of Michigan. Call it a split decision that depends entirely on how hungry and how patient you are.
The final scorecard
Date night or a birthday table: Emmy Squared, ideally with the Colony and a round of the Le Big Matt for the table. Casual night out with friends, beers, and a controller in hand: Ace's in Williamsburg. Fastest excellent square in Manhattan, no chairs required: Mama's TOO! on either side of the park. And when someone in the group chat starts litigating the best deep dish pizza in Chicago versus everything else, the correct answer is to book the next flight or, far cheaper, walk them into one of these three rooms and let the corner piece close the argument. One timing tip that applies across the board: squares are a pan product, so they come out in waves — a piece cut minutes after the steel leaves the oven beats any reheated slice, which is one more reason an off-peak weekday visit is the connoisseur move.
Practical notes
Emmy Squared (83 First Ave) is closest to the L at First Avenue and the F at Second Avenue; it opens at 11 a.m. daily and holds bar seats for walk-ins. Ace's (637 Driggs Ave) is a short walk from the Bedford Avenue L stop, open noon to 11 p.m. Sunday through Thursday and until midnight Friday and Saturday — no reservations needed for small groups, and takeout moves quickly. Mama's TOO! is slice-shop format at both the Upper West Side original and the Bleecker Street shop in the West Village; expect a line at peak hours that clears fast. All three take cards. Corner squares go first everywhere, so arrive early in the lunch window if you care about maximum crispy edge.
Tags: #nyc #nycpizza #detroitpizza #crispysquares #emmysquared #williamsburg #eastvillage #westvillage #nycrestaurants #pizzalover #squarepizza #deepdish #nyceats #foodbattle
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Ask Karpo first
Curious which square shop has the shortest line right now, whether the corner pieces are likely gone, or how to fit two of these pizzerias into one afternoon? Ask Karpo for the latest Detroit-style pizza updates, a pick matched to your night, and a live route between the East Village and Williamsburg before you head out.
