The Family Man (2000), a mystical holiday rom-com of second chances starring Nicolas Cage, Téa Leoni, and Don Cheadle, features a key scene shot on Broadway between West 68th and 69th streets. In it, Cage’s character, financial hotshot Jack Campbell—lover of fast cars and fast women—has an unforgettable meltdown. Often described as a modern take on Frank Capra’s It’s a Wonderful Life, the film is currently streaming on Netflix.

The movie begins with Jack Campbell and Kate Reynolds (Téa Leoni) at the airport, locked in an emotional farewell. As they kiss and hold each other tightly, Campbell starts to walk toward the gate when Reynolds calls out, “Wait! I have a really bad feeling about this.” Both are fresh out of college with exciting career opportunities: Campbell has an internship at Barclay’s Bank in London, while Reynolds has been accepted into one of the best law schools in the country.

Campbell sees this as the perfect opportunity for both of them, but Reynolds suddenly wants to “flush the plan.” She chooses being together over everything else, uncertain of what their future will look like but convinced that love is enough. “The plan doesn’t make us great, Jack. We make us great.” Campbell kisses his girl passionately in an embrace and says he loves her. “One year in London won’t change that,” he reassures Reynolds before walking to the gate.

ALSO READ: 30 Rock Locations on the Upper West Side!

The film jumps 13 years ahead, cutting to Jack Campbell lying in bed in his upscale New York City apartment, casually reading the newspaper. “Last night was incredible,” says a new woman in Jack’s life as she gets dressed. “You are an amazing lover,” he replies smoothly. Jack expresses interest in seeing her again, but it’s Christmas Eve, and she’s heading to New Jersey to spend the holiday with her parents.

Unfazed, Campbell struts alone through his luxurious penthouse apartment, singing La donna è mobile by Luciano Pavarotti. As he glides into his expansive walk-in closet—complete with breathtaking views of the city—he belts out the opera with flair. This moment will come full circle later. Campbell dons a sharp power suit and heads to the elevator, where he continues his operatic performance. Enter Mrs. Peterson, who quips, “You don’t have to stop singing on my account.” Campbell, with a grin, claims it’s because he’s shy, then cheekily asks, “When are you going to leave that old corpse, Mr. Peterson, and run away with me?” Without missing a beat, Mrs. Peterson fires back, “You know you could never satisfy me the way he does.”

The film shifts to sweeping views of the city adorned in festive Christmas regalia. The iconic Christmas tree at Rockefeller Center takes center stage before transitioning to scenes of Central Park. Campbell drives his sleek gray Ferrari past Sheep Meadow and Tavern on the Green, capturing an era when cars still roamed those roads. In the distance, the grand facade of The Plaza Hotel looms, completing much of the quintessential New York holiday backdrop.

ALSO READ: The Breakup Scene from “You’ve Got Mail” was Filmed at this Forgotten UWS Haunt

It’s Christmas Eve, and Campbell has his team laser-focused on work. When one of his employees appears distracted in the boardroom, Campbell brushes off the holiday with, “Is that tonight?” As the president of his financial firm, Campbell openly admits to having tunnel vision when it comes to business. His focus is fixed on the announcement of one of the largest mergers in U.S. corporate history. “December 26. After that, there’ll be so much money floating around here, it’ll be like Christmas every day. December 26—you can celebrate that day.”

Back at his office, Campbell gets an interesting message from his secretary; it’s from his old love, Kate Reynolds. “I almost married her,” he says to the shock of his secretary, who laughs and says, “You, married?” Campbell says it wasn’t easy; he took the road less traveled. His secretary is amused, so she wants to get her on the phone right away. “She’s probably just having a fit of nostalgia, you know, lonely Christmas Eve, call the one who got away.”

ALSO READ: Seinfeld Locations on the Upper West Side!

In comes the CEO, Peter Lassiter, played by Josef Sommer, impressed that Campbell is still at his desk at 8:35 p.m. “Now there’s a Hallmark moment for you,” he quips. When Campbell asks why Lassiter isn’t home trimming the tree, the CEO dryly replies that it’s because he’s a heartless bastard who only cares about money. When Campbell seeks his advice about calling the one that got away, Lassiter remarks, “Old flames are like old tax returns—put ’em in the file cabinet for three years, then cut ’em loose.”

When Jack finally leaves work, it begins snowing as he steps out onto the street. He decides to take a stroll and stops at a bodega to grab some eggnog. It’s there that he runs into Cash (Don Cheadle), who’s sporting a backward Phat Farm hat with a blunt wrap tucked in it. Cash tries to cash in a winning lottery ticket for $238, but the cashier tells him the ticket is fake and asks him to leave. Cash pulls out a gun and a mother screams, clutching her baby. Jack steps in, offering Cash $200 for the ticket so he can make a quick $38. After a tense standoff, during which Cash, oddly enough, knows Jack’s name and asks if he wants to die, Cash ultimately accepts the deal.

“How did you know my name was Jack?” Campbell asks outside. “I call all you guys Jack,” replies Cash. Suddenly, Campbell wants to help the stranger, talking about programs and opportunities that could help him. “Are you actually trying to save me?” laughs Cash. “This man thinks I need to be saved, y’all!” he yells to the heavens. Campbell tells Cash that everybody needs something, prompting Cash to ask, “What do you need?” “I’ve got everything I need,” Jack responds. Cash is amused, saying he’s got a little something coming for Jack. “I’m really going to enjoy this. Just remember, you did this, Jack. You brought this on yourself. Merry Christmas.”

Campbell goes home, throws his overcoat on a chair, and gets into bed. The camera starts fading to black.

With enchanting music playing, a soft light casts over Jack’s face as the camera pans in close. He raises his head, once, then again, and his expression shifts to one of bewilderment. “Just ten more minutes, Jack,” says a sleepy Reynolds, his old love from the airport. Their two kids burst in, singing “Jingle Bells, Batman Smells,” and a dog barks happily. Jack jumps out of bed in startled shock. He scrambles to put on his clothes and rushes out of the room. Racing toward the exit, he bumps into Reynolds’ parents and asks, “Where’s my Ferrari?”

“What the hell are you talking about?” Reynolds’ dad asks, confused. “You’ve got a perfectly good minivan sitting out in the driveway.”

Jack drives straight to his ‘old’ apartment at 2000 Broadway, between West 68th and 69th streets, hoping to snap back to his previous life. You can spot the black gate in the middle of the Broadway median, flanked by Christmas trees—likely added by the production team to complete the holiday vibe—and the bottom of the Dorchester building across the street. Uh-oh, the doorman doesn’t recognize him and informs him that the building is for residents and guests only. Mrs. Peterson walks by at that moment. “Who is this man?” she notes, slightly repulsed. “What is this, a Christmas joke?” asks Campbell.

Jack is flabbergasted. He tries to remind Mrs. Peterson that they’re on the co-op board together, that they fought side by side for garbage disposals, and that every morning they share their witty, quasi-sexual elevator banter. The doorman threatens to call the cops. Mrs. Campbell, however, wants to help, suggesting there’s probably a shelter they can get Jack into.

“What are you, smacked out of your head?” a melting-down Campbell demands. “I’m the richest man in this building! I’ve got twice the square footage you have, and I’m going upstairs!” But once again, Campbell is blocked by the doorman.

“Not cool! Not cool!” Furious, he storms toward his new minivan, threatening to have the doorman fired and warning Mrs. Peterson that she’s now on notice with the co-op board. To top off this blazing hot fiasco, Campbell’s minivan refuses to start.

What’s intriguing about this scene at 2000 Broadway is that there’s no way this building could have had the views Campbell enjoys while getting dressed earlier in the film. ILTUWS looked into it and discovered that the penthouse scene was actually filmed at 641 Fifth Avenue, between East 51st and 52nd streets. This building, known as Olympic Tower, is a 51-story structure in Midtown Manhattan. “Built in 1975, it was constructed on the site of a Best & Company Store that opened in 1947,” according to On The Set of New York.

Can you believe we’re only 22 minutes in? Kudos to the production team for avoiding shots of the AMC theater at 68th and Broadway, which would have further given away the off-location filming.

I won’t spoil what happens to Jack—he’s about to live the life he might have always wanted.

Have a news tip? Send it to us here!