Joshua Goldman
Joshua Goldman
min read · June 21, 2025 · Entertainment

Leo’s Elite Evening: Inside Leonardo DiCaprio's Exclusive Dinner at Rao's

Leonardo DiCaprio pictured at NYC¿s notoriously exclusive Italian hotspot Rao¿s, where he dined with political and media power players

JAW-DROPPING CELEBRITY ENCOUNTER AT LEGENDARY EATERY!

In a move that's got everyone talking, A-list actor Leonardo DiCaprio was spotted rubbing shoulders with political bigwigs and entertainment moguls at Rao's, the iconic ten-table Italian joint in East Harlem. The 50-year-old Oscar winner made sure to bring his A-game, dining alongside Nassau County Executive Bruce Blakeman and entrepreneur Andrew Murstein - who just so happens to be hosting the evening's festivities.

But let's get real, folks - the real head-turner was Blakeman's impressive security detail. That's right, we're talking about a whopping FIVE security guards just for him! Meanwhile, DiCaprio was busy charming fans and friends with selfies and video chats on FaceTime. Talk about being a good sport!

The 125-year-old ten-table dinner spot doesn't accept walk ins or reservations and there is virtually no way to contact the restaurant unless you have an 'in' - even if you're a celebrity

Now, what's really got everyone buzzing is the top-secret meeting that went down during dinner. Apparently, Blakeman was pitching his vision to transform Nassau County into Hollywood East - a move that could bring in a whopping $533 million in economic impact, just like Grumman and Gold Coast Studios did when they filmed scenes from Wolf of Wall Street.

But what's even more fascinating is the lengths people will go to get a seat at Rao's. I mean, who wouldn't want to dine alongside Hollywood royalty? The catch? This restaurant doesn't take reservations - or walk-ins for that matter. You need an "in" to get in. And let me tell you, those with connections are willing to shell out big bucks for the privilege.

Case in point: one seat at Rao's recently went up on CharityBuzz for a whopping $20,000! That's right, folks - the exclusivity of this eatery is so extreme that even celebrities struggle to get through the door. But don't worry, there are people like Nicky DiMaggio who can make it happen.

Leo reportedly was 'extremely friendly' and 'took dozens of photos with fans and hopped on at least five FaceTime calls' while dining at Rao's (Pictured: Leonardo DiCaprio attending the Opening Ceremony of the 78th Cannes Film Festival on May 13, 2025, in Cannes, France)

This professional reservationist has cracked the code and charges clients anywhere from $500 to $1,000 to get them into Rao's - or any other exclusive restaurant in New York City for that matter. And let me tell you, his services are in high demand. After all, people want what they can't have, right?

So, who else has managed to snag a spot at Rao's? Well, the likes of Al Pacino, Woody Allen, Frank Sinatra, Robert De Niro, Donald Trump, Pete Davidson, Kevin Costner, and Bethenny Frankel have all dined at this legendary eatery. And let me tell you, it's not just the rich and famous who can get in - with the right connections, anyone can experience the magic of Rao's.

STAY TUNED FOR MORE SCOOP AND GOSSIP FROM THE SCHOLARLY NOTE!

Nick DiMaggio is a professional reservationist who scores the most coveted tables in NYC (Pictured: Nicky DiMaggio (center right) joins famous food critic Jonathan Cheban (far left), better known as Food God with two of their friends at Rao's in April 2019)

The exclusivity is so extreme, one seat at Rao's recently hit $20,000 on the bidding site CharityBuzz (Pictured: Pete Davidson attending Rao's Restaurant pop-up in February 2025 in New Orleans)

Other famous celebrities have been seen dining at Rao's over the yeara include Al Pacino, Woody Allen, Billy Crystal, Frank Sinatra, Robert De Niro, Donald Trump, Danny Aiello, and Nicholas Pileggi (Pictured: Kevin Costner attends Rao's Restaurant pop up in New Orleans)

Pictured: Tommy Mattola and Mayor Adams at Rao's