Sweet Taste of Success as Iconic UES Restaurant Marks 70 Years

Chef Joe Calderone is the man behind some of the sweetest and eccentric creations at Serendipity 3, the famous Upper East Side restaurant that has been a culinary institution in Manhattan since 1954.

The Long Island City native joined Serendipity in 1986, and as its creative director, a typical day for him includes creating menu items, curating the gift shop, creating branded merchandise and even earning Guinness World Records.

“Every day is different, and that’s what I love so much about my job, because it’s never boring,” said Calderone, a dad of three who lives in Port Washington, NY.

Calderone, 62, has spent his entire life living and going to school in New York, and attended Peter Kump’s New York Cooking School, now called the Institute of Culinary Education, and Baruch College, where he earned a degree in marketing and advertising.

September will be a milestone month for Calderone as Serendipity will celebrate its 70th anniversary, and to mark the incredible feat, will be reverting to its original 1954 menu price of their famous Frrrozen Hot Chocolate at $1.00. And on September 5th, Serendipity will be opening a new location in the heart of Times Square at 157 West 47th Street in the OYO Hotel.

You’ve said your interest in cooking started in your Italian grandmother’s kitchen.

Yes, it was my Sicilian grandmother. She lived in this little cottage upstate and would grow all her own vegetables and fruits. Going there, it overtook your senses, just the smells. She had a tiny kitchen, but she used to make incredible meals out of that. And my brother and myself, we were always part of that. She put us to work as soon as we got there. [Laughs]

Tell us about your educational and work background.

I have a very varied background. I graduated high school in 1979. I didn’t know what I wanted to do, so I started business school, and I dropped out. Then I went to Peter Kump’s New York Cooking School [now called the Institute of Culinary Education] because I just loved food and I knew I wanted to work with food in some way. And as I was at Peter Kump’s, I loved it, but the thought of being in a kitchen in the heat for 12 hours was a big turnoff. I loved the PR and marketing part of food the most, getting the word out there and curating incredible photographs and things like that. So I left cooking school and went to Baruch and I got my degree in marketing and advertising. And I started doing PR and marketing for arts organizations like the Joffrey Ballet and New York City Ballet, but it wasn’t me, I just didn’t feel it.

How did you get your start at Serendipity?

I had this opportunity to come to Serendipity in 1985 and they, at the time, had a location here in New York and they had one in Boston in Faneuil Hall. And they wanted me to revamp Faneuil Hall, so I joined, and almost 40 years later, here I am.

How did all your Guinness World Records come about?

I reached out to Guinness and they were so excited about the possibility of working together that they kind of fast-tracked our application. The first opportunity to work with them was kind of a last minute decision in 1998, where we did our first Guinness World Record, which was the world’s largest wedding cake. It was a 2,000-pound, 10-foot tall cake and we pulled it off, made it in nine days. And then I, of course, always have to add other layers. We had a wedding take place, this was Valentine’s Day, and on that day we had a couple get married for the 59th time to each other, and then we had the world’s largest wedding cake to celebrate.

What happened to all the extra cake?

A really cool backstory that I always have to tell is on that Valentine’s Day, every soup kitchen and homeless shelter in New York had a piece of that cake. I could not let it go to waste and I didn’t want to just give it away. So we spent 20 hours cutting, plating, refrigerating and then transporting it all over the city. One of my first jobs in the restaurant field when I was at Baruch was I managed a bar/restaurant in SoHo called the Wine Bar on West Broadway. It was literally two blocks away from The Bowery Mission. And I would drive home to Queens every night at like 3 or 4 in the morning and pass this mission and see people waiting on line to get food and I had just thrown out tons of food. So I started a relationship with The Bowery Mission, bringing food to them every night on my way home. It was such a great partnership. Years later, we’ve done collaborations and fundraisers for The Bowery Mission because it’s an organization that’s very close to my heart.

What are some other Guinness World Record items you created there?

One of the next items we did was–we’re famous for selling our footlong hotdogs–so we did a Foot Long Haute Dog, an elevated version. It was Kobe beef, cooked in white truffle oil in a German pretzel bun topped with pâté of foie gras. And then on the side we had house-made heirloom tomato ketchup, Vidalia onions cooked in white truffle oil and truffle-infused Dijon mustard. That hot dog was $69. We did the world’s most expensive hamburger, Le Burger Extravagant, which is a Japanese-ground Wagyu infused and stuffed with 10-herb white truffle butter topped with Montgomery cheese on a roll dusted with 23-carat edible gold. And then that had a little tiny toothpick with a blini, creme fraiche and Beluga caviar. It was $295 and that did incredibly, incredibly well and we got recognition from around the world. For Serendipity’s 50th Golden Anniversary, I came up with a Golden Opulence Sundae [the most expensive sundae in the world at $1,000]. That blew up around the world. We had everyone from Saudi princes coming in with cash and buying them for their entire table to a dad buying it for his daughter who just graduated law school. It was an edible work of art, really.

I interviewed you back in 2022, when you were about to serve your 30 millionth Frrrozen Hot Chocolate.

Yes, and we wound up serving that one to Cher and Jimmy Fallon on “The Tonight Show.”

North West [Kanye West and Kim Kardashian’s daughter] had her birthday party at Serendipity recently, right?

Yes, she did. North had her 11th birthday here, and Kim was here. And it was a beautiful party; she had a great time. We actually just did the Zuckerberg’s daughter’s party here. August Zuckerberg [daughter of Mark Zuckerberg and Priscilla Chan] turned 7 and we had a big party for her.

What are your bestsellers?

A lot of people don’t realize we have one of the best burgers in New York. And we have an infamous truffle burger that is pretty delicious and outrageous. We have a whole line of incredible macaroni and cheese. We still have our famous foot long hot dogs, and we just added a bunch of new ones, including a mac-and-cheese foot long with Panko breadcrumbs and shredded cheese and then that’s toasted. It is so, so, so good.

What is the most interesting customer request you’ve gotten?

Well, I have a funny one that was from Elaine Stritch, the Broadway actress. She would come in and she would ask for a cup of hot water, and then she would go into her purse and take out her own tea bag. She liked her tea is how she put it.

There have also been a bunch of movies and TV shows filmed there.

We filmed “One Fine Day” with George Clooney and Michelle Pfeiffer here in 1996. Then we did the movie “Serendipity,” and that film came out right after 9/11. That was the first film to premiere in New York City after 9/11. And a lot of people felt that it was kind of like a love letter to New York and I think everybody really needed it at that time. After that, we filmed “Trust the Man” with Julianne Moore and David Duchovny. We filmed episodes of “Glee.” We had all “The Real Housewives” here. We’ve had the Kardashians filming here. We filmed a scene in “Lyle, Lyle, Crocodile” with Javier Bardem. And I can’t really talk about it, but we’re in talks about filming a holiday movie here sometime late December, early January.

To learn more, please visit www.serendipity3.com.