A Dandy on the Big Apple

Go behind the tourist façade to the pulsing heart of New York. Band leader and jazz singer Dandy Wellington guides you

Q&A with Winston Chesterfield

Jazz belongs in New York City, and so does Dandy Wellington. Not because it necessarily deserves either, but because it needs both. The Apple is a tough, unforgiving place with bucketloads of attitude. It is packed to the rafters with commerce and trade, hagglers and hawkers, brokers and bankers, so it needs art and artists. And this is where Dandy has one up on jazz; he’s both art and artist.

Very few people today in New York are bona fide jazz singers and bandleaders, and there are virtually none who could be compared to the great entertainers of the early 20th century, such as Duke Ellington or Cab Calloway, the charismatic doyennes of Harlem’s notorious Cotton Club. But Dandy Wellington is the exception, not the rule.

As an entertainer, he is complete. In addition to his role as a singer, dancer and bandleader, he also writes his own jazz songs, but it is his brilliant style and his energy and magnetism that deliver the definitive splendour to his persona. When most people think of live jazz bands, they think of glum-looking saxophonists wearing three-day stubble, drab black shirts and jeans. Dandy’s answer to this is utterly pyrotechnical; a blaze that is bringing back the smiles, the bow ties, the happy buttonholes and the fun that jazz once had.

What’s your neighbourhood?
My favorite New York neighborhood is Harlem. Being born and raised there, I know I’m biased but it truly is a beautiful part of the city. From its complex and beautiful history to its cultural diversity to its picturesque architecture, Harlem has something for everyone.

Where would you go in New York for a nightcap?
It depends on what neighbourhood I’m in. If I’m in Tribeca, Macao Trading Company (The Odd Job). On the Lower East Side, Hotel Chantelle (The Libertine). In Chelsea, Norwood Club (Guns & Rosemary). In Nomad, Henry at The Life Hotel (South By East Side). On the Upper West Side, Maison Pickle (Jacob’s Collins). In Harlem, Vinateria (Uptown Bellhop) or Clay (Good Morning Heartache).

Most romantic place in New York?
The Central Park Conservatory Garden and Wave Hill Public Gardens

Shops you rely on in New York?
In Brooklyn, Sean Crowley Vintage.
In Midtown, Fine and Dandy Shop.
In Harlem, Flamekeepers Hat Club

Favourite club in New York?
Norwood Club in Chelsea. It’s like my home away from home.

Photograph by Bek Andersen

Best meal in town?
Hands down, Maison Pickle or Jacob’s Pickles.

Earliest New York memory?
My earliest memories in New York have to be running errands with my Mom. I’d accompany her to stores all around the city, traveling from the Lower East Side to Upper West Side to Harlem and beyond. That’s how I learned the neighbourhoods.

Building you’d most like to buy in New York?
A townhouse on Stiver’s Row in Harlem. These historic houses are picturesque with bay windows and gates where horse drawn carriages would have entered the property. They are a beautiful piece of history and should be preserved.

Best thing a New Yorker has said to you?
I’ve lived here all my life, so that’s a tough question. However, nothing beats getting directions from a New Yorker. We’ll get you where you need to go but we’ll only tell you once because we most-likely have somewhere else to be.

What’s your secret vice?
Ice cream….. but that’s not a secret.

What do you collect?
Men’s dress hats. (Boaters, Derbys, Top Hats, Fedoras)

What’s your best-kept secret in New York? 
Freeman Alley – a “mews” off Chrystie Street.
Untermeyer Gardens Conservancy – A historic garden in the Yonkers.

Building you’d like to be locked in overnight?
The Metropolitan Museum of Art

What would you do as Mayor?
Fix the Subway System and build more subsidized housing for lower income New Yorkers.

Where do you go for musical inspiration?
Fats Waller, Louis Armstrong, Duke Ellington

Best piece of advice you’ve been given?
Work smarter, not harder. – Anton Briones
Inspire, till you expire. – Giovanni James
If you don’t see yourself being represented, go out and represent yourself. – Murray Hill.

Who are your musical heroes?
Fats Waller, Louis Armstrong, Fred Astaire, Duke Ellington, Noble Sissle, and Giovanni James. riddle_stop 2

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