Frank: A Musical Journey


A Visitor’s Guide to Sinatra’s New York

In my line of work, it’s a good thing I love to travel. There’s a certain almost-inexplicable excitement that shoots through me when I arrive in a new city, a cresting of anticipation that never fails to imprint a smile upon my face as my latest adventure begins. It’s a hobby of sorts to learn as much as I can about admired celebrities then apply that knowledge to seek out their favorite landmarks in a particular city. Today I plan to take you through some of the Chairman of the Board’s New York haunts.

Frank loved a night out, so there’s no shortage of beloved restaurants and clubs he would frequent, but some may be surprised that they usually aren’t typical hangouts of the stars, he preferred somewhere he could be comfortable with his friends – staff and owners of the establishment often included – and enjoy as much public privacy an icon as monumental as Sinatra could possibly procure.

So, it’s no shock that his closest pal’s spot, Jilly’s, was his favorite. The lounge no longer exists as Jilly’s, but it’s possible to visit the location by stopping at the Russian Samovar at 256 W. 52nd Street.

The next obvious must-visit spot is Patsy’s Italian Restaurant at 236 W. 56th Street. This place was so important to Frank in good times and bad I’ve already written about it and a particular memorable Thanksgiving meal.

Next, stop, maybe for the night, at the Waldorf Astoria at 301 Park Avenue, where Sinatra lived in the suite that was once home to Cole Porter. Apparently the staff had standing orders to open the bar in the ballroom at any hour should The Voice want to entertain some friends.

You want pizza?! It’s a New York staple, so for some joints Frank enjoyed visit Monte’s Venetian Room in Brooklyn – the cheesecake was a favorite – or Grimaldi’s Pizzeria, also in Brooklyn. Frank reportedly had these pies flown to him in Las Vegas.

Ol’ Blue Eyes had his first solo show at the Paramount Theatre on Broadway and although the theatre is no more, you can still see the place as a Hard Rock Café.

The ‘21’ Club at 21 W. 52nd Street was a popular spot for Sinatra to entertain and it’s still there. P. J. Clarke’s can also be found at 915 Third Avenue, right where it was when Frank would hold court.

Next time you’re in the Big Apple, hit as many as these spots as you can and revel in the history that surrounds each and every one of them.