After some lovely footage of the day beginning in various parts of the city, an explosion occurs at the Bonwit Teller department store on Sixth Aevnue. A man claiming to be the bomber demands that McClane, who is currently suspended from the police force, be put back in action and do as "Simon says" or another bomb will be set off.

The first thing Simon says is for McClane to be dropped off at the corner of 138th Street and Amsterdam Avenue in Harlem wearing a very specific and inflammatory sandwich board. In the movie, Washington Heights stands in for Harlem, with McClane having actually been dropped off at the corner of West 176th Street and Audubon Avenue. An old lady is extremely unhappy about McClane's sign, but we don’t yet know what it says.

Washington Heights is still standing in for Harlem, complete with a street sign indicating the corner of Lenox Avenue and West 138th Street. The camera zooms in to show two kids walking into an appliance shop run by Zeus Carver. When the kids, Zeus's nephews, leave the store, they tell him that there’s an unusual white man on the street. That’s when we see what McClane is wearing. It’s a very, very racist sign, one designed by Simon to antagonize the locals.

This is McClane’s second assignment from Gruber. Simon calls them on the payphone outside the station—with Gray's Papaya in the background—and after toying with their minds and emotions with a riddle, he says that a downtown 3 train will be destroyed by an explosion unless they get to a payphone in the Wall Street station in 30 minutes. If they use any non-civilian means to get there, Simon says he’ll destroy the train. If they try to evacuate the train, he will also destroy it. So naturally, McClane forces a cab driver out of his car, and they start speeding downtown.

McClane uses the park as a shortcut to get part of the way downtown—not Park Drive, but literally the park. McClane takes the cab off-roading, careening over hills and winding through wooden pathways, barely avoiding crowds of park-goers. When they catapult out at the southern end, McClane says, "72nd and Broadway to Central Park South in three minutes. Gotta be a fucking record."

After nearly getting trapped in traffic, they barrel through Columbus Circle to make their way to Ninth Avenue. McClane has radioed in that a cop is down at 14th Street and Ninth Avenue, which means an ambulance will be dispatched from Roosevelt Hospital and they can follow it to speed up their journey.

Now occupied, the lot across the street from 28 Liberty Street (aka One Chase Manhattan Plaza) was an empty one in 1995, so it was used to construct a fake subway entrance for the Wall Street station. They didn't quite get the font right (the official font of the NYC subway system is Helvetica), and the interior is also a fiction, as it is a much bigger platform than the actual Wall Street 2/3 station. Though McClane throws the bomb off the train, it still goes off and the train derails.

Simon says there is a bomb in a school somewhere in the city, and he orders McClane and Zeus to Tompkins Square Park for a clue as to where the bomb is and how to disarm it. With basically every available resource being used to search the city’s schools for a bomb, the subway disaster site is left nearly unguarded. Simon and his henchmen use a small tunnel boring machine to drill into the Federal Reserve Bank of New York and steal the gold.

McClane and Zeus are seen running uptown. It doesn’t really make sense for them to be in Greenwich Village if they’re headed to Tompkins Square Park from Wall Street, but it does look cool with the Twin Towers behind them.

McClane and Zeus steal yet another car to chase down Simon and his trucks. They stop and get out of the car on the exit that leads to the Brooklyn Bridge. McClane doesn't see them on the bridge, but Zeus sees them up on the FDR Drive (where trucks are not allowed in real life).

By the magic of the movies, when they get back in the car, they are seamlessly going down the ramp that takes you from the inbound Brooklyn Bridge to the northbound FDR Drive. They lose the line of trucks, but spot a singular truck and stop it. It turns out to be a friendly driver headed to Water Tunnel 3. McClane realizes that Simon has used the water tunnel to get the trucks and gold out of the city. He heads into the tunnel while sending Zeus to Yankee Stadium for yet another clue.

Zeus arrives at Yankee Stadium to find a message: "GAME OVER." It seems that Simon had intended to have Zeus and McClane executed by a sniper at the stadium, but with only Zeus there, the order to shoot is not given. Zeus then leaves and drives north to meet up with McClane at the Westchester exit of the water tunnel.