The Life of Riley

a quest for the good life in New York City and beyond


New York City Writers

A Brooklyn Retrospective

From a young age, Jerry Castaldo fell in and out of bad behavior, trying relentlessly to break away from the violence and bad influences in his life. In Brooklyn NY: A Grim Retrospective, Castaldo proves that our situations do not define us. Raw and honest, Castaldo’s story doesn’t hold back. Scattered with celebrity and influential New Yorker encounters, readers applaud Castaldo’s gutsy and relentless journey to entertainer success and to a healthier lifestyle. I  caught up with Jerry recently, asking questions about the book, his troubled past, and his thoughts on success, giving back, and of course New York.

Riley: Do you feel as if you’ve lived a hundred lives?

Jerry Castaldo: First off, thanks for having me talk about my book. Actually, I feel that I’ve lived three distinct lives, with the third one being where I am right now. I was a good kid, and then went the wrong way due to intense, violent peer pressure while growing up in NYC, and now I’m back to who I was at the beginning.

Riley: How does the New York you grew up in differ with today’s New York?

Castaldo: I really don’t think New York has changed much, except of course for the difference in a variety of ethnic groups living in what used to be neighborhoods with only one or two specific ethnic groups. For instance, Bensonhurst, Brooklyn was predominately Italian during the ‘70s and now there’s been an influx of Russian, Chinese and other different nationalities populating that particular neighborhood.

Riley: One of the best things you say in Brooklyn NY:A Grim Retrospective is in the opening: “I so desperately want people to see how a good person is basically good, regardless of where he or she may falter and go astray; and sometimes–but not always–that person can get back to the beginning. You feel like you’re back at the beginning in your life today. Explain that idea a little more.

Castaldo: Thank you for saying that. Again, to reference what I said earlier, yes, I am back to whom I was before I changed into that other person. Back then, it was not by choice, but to protect myself. I morphed into your standard Brooklyn “tough guy,” although it was all an act. I started to commit terrible crimes and became heavily involved in drinking and hard drugs. When I wanted to stop and go back to the old me, I couldn’t. I didn’t know how to and I wallowed in misery and horror for about fifteen years. I’ve been called a “cat with 9 or more lives” in many of the (Five-Star) reviews of my book on Amazon, because of the many near death experiences that I suffered. The “Death by Subway” chapter is probably the most disturbing chapter in the book, or so people tell me.

Riley: How has recognizing addiction changed your life?

Castaldo: Back then, I’d always recognized addiction as a negative thing in my life as well as other people’s lives, but that never propelled me into action, to get clean or anything. I just lived that life until I couldn’t’ take it anymore. Then I started to investigate what groups were out there that could help me kick. I never imagined that all these years later, my tormented existence would translate into a Top Rated book. It just blows my mind to see it number one on Amazon in five or more different categories, including Self-Help. This is just amazing to me, to see it number one in self-help. I never would have imagined this.

Riley: You sought out help and found a better way of living. Have you been able to pay it forward?

Castaldo: After years of trying to get sober and out of that lifestyle, always trying to do it on my own (which never worked), I reluctantly entered rehab multiple times. I then finally followed up the last time with intense group therapy, every single day, sometimes twice a day, for over a year. I now find myself often writing letters to people in jail at the urging of their relatives who have read my book. I take the time and make the effort because I do want to help others.

Riley: Without a doubt, you are a survivor. What advice can you give to others who struggle, whether with current economic times, job loss, etc.?

Castaldo: I’ve been sober now for twenty-one years, and have made a decent living as an entertainer, but I have seen a decrease in the amount of available cash that organizations have to spend on entertainment during the last 3 years of our economic downturn. As disappointing as this is to me and to all of us, I just need to stop and remember that I’m not addicted to drugs and alcohol anymore, my health is good and I have the ability to work and earn money in the future. So how could I feel sorry for myself? I do know, understand and sympathize with others who may be going through an even worse time economically, and I try in any way I can to help. A national Women’s organization wanted to book my show, even though they had more limited funds than last year, and I decided to take a pay cut because I didn’t want to turn them down. I’ve been doing this more and more over the last two years, but again, I want to help and I live and love to work.

Riley: What do you love most about entertaining?

Castaldo: I guess it’s just built into me. From a very early age I always loved creating something from an idea and then executing it in front of an audience. The reward was, and is, that I feel like I’m actually doing something to bring people out of their own world and into mine for a few minutes. And as much as a cliché as this may be, I want them to forget about their own life and problems for a while.

Riley: What projects are you busy working on now?

Castaldo: Ha, ha. I’m laughing because I just don’t stop moving. I continue to log hundreds of one hour shows per year, mostly in the northeast and some in Florida, but I’ve also been putting together acting scenes and monologues for a new acting reel that a New York City agent has asked me to compile. He read my book and wants to represent me now. I’ve just posted an acting scene from the classic Broadway stage play/film, “The Owl and the Pussycat” on You Tube and also on my Facebook page. Back in the ‘80s I’d done some acting and had garnered some decent reviews, so I’m happy to be doing it again.

Riley: I think your story could be a wakeup call for teens. Have you considered reading your book at events for troubled teens?

Castaldo: Yes, I’ve been asked to speak for many teen groups, and if I am not working and I can do it, I’m always there. When I was younger, my mom and aunt tried to have me committed to a rehab/psych ward in New York City and I resisted. Just last year, that same rehab center did a mass buy of my book, 50 copies, and made it required reading for their patients, right there alongside AA’s The Big Book. I’m told by workers that they’ll walk down the hallway of a wing and see patients sitting on the floor reading my book. That’s very rewarding to me.

Riley: All New Yorkers have their own version of their “New York.” What’s Jerry Castaldo’s New York?

Castaldo: My New York? I don’t hate New York or my old neighborhood in Brooklyn because of the terrible time that I experienced there. Everything that happened to me was brought on by my own bad choices and later by my physical and emotional addictions to drugs and alcohol. I never put Brooklyn down in my book. I do point out the negative influence I experienced in that particular “mob-run” neighborhood back then. If I had a choice, yes, I would have preferred to grow up out in the country someplace, but that doesn’t guarantee a perfect existence either. New York is a great place. Although I now live in the hills of western New Jersey and go into Manhattan only for auditions, meetings and entertainment. It’s a shame that back in the ‘70s they had a saying, “New York is a nice place to visit, but I wouldn’t want to live there.” Uh oh, wait a minute, didn’t I just say that myself? Oops. 🙂

Jerry Castaldo has been performing for audiences ever since he started a band at age 12 while growing up in New York City. While playing guitar and singing in different groups, Jerry learned to incorporate bits of comedy into his act during his late teens. This helped him secure numerous assignments as a Master of Ceremonies in and around Manhattan.
From there, and through his 20’s, Jerry went on to successfully host and perform at countless affairs for social, civic and fraternal organizations, as well as hosting The International Beauty Show at The Jacob Javits Convention Center in NYC. He was also the Master of Ceremonies and main performer for a national promotional tour for Revlon Inc.

To learn more about upcoming shows, visit Jerry at and connect on Facebook.


A Writer, The Big Apple and the Great Escape

By: Guest Writer Natasha Guadalupe

The best place to write is in your head”, Ernest Hemingway succinctly once said.  As a writer living in New York City it’s a concept you practice by force.

Between the 400 square foot one bedroom apartments, if you’re lucky, multiple roommates, overcrowded trains, overpriced restaurants; full-time jobs or many small ones; you ultimately feel like all your laborious efforts are merely an attempt to not fall behind; not even taking into account the required time or energy for the development your true passion—writing.

One of the pitfalls on the road to becoming a committed and purposeful writer, I’ve often fell into the trap of feeling overwhelmed by the City with its wealth of opportunities. Knowing of their availability but not quite understanding how and where to attain them.

I did what a typical New Yorker would do in the event of having to engage with a stranger on a train, I stood my ground and made no actual eye contact; or better said, I remained typing away on my worn laptop, sipping my third cup of Starbucks tea wondering if I was alone in feeling this way.

It was only when I saw a random flyer advertising an open ‘mic’ night or spoke to a fellow writer about a free course at the Annex the truth pushed its ugly face forward. I was missing out on the things that are crucial to any writer’s life: connecting, learning and writing.

New York City is a hotbed continually producing world renown and influential writers; it is clear it’s the environment conducive to attaining resources to those who seek them out. So, over the last six months I decided to retool my artistic process strategy for better effectiveness. By doing so I’ve been able to meet inspirational people, find stimulating places write, share my work and participate in writing groups.  Wondering how I manged to completely overhaul my situation?It was exceedingly simple; I gave myself time to actually see what was right in front of me.

Once I started looking for opportunities finding them became easier. One of the basics was realizing how the city itself has responded and augmented internet availability. Also, the advent of public seating in traditional and non-traditional spaces is a huge plus and a carry over from our current boon of telecommuting.

Schools, writing annexes and even libraries are offering free or low-cost writing courses. While businesses such as coffee shops and even museums have adapted their services by offering free Wi-Fi and creating writing friendly lounges and communal seating for cafe patrons.

Below I have listed various resources and outlets for all types of writers to find conducive spaces to write, free/ low-cost writing courses and networking outlets for you to connect with other writers, be they unpublished (like me) or published writers.

From one writer to another I will leave you with my own personal tip when trying to find time to write within the hustle and bustle of New York. What’s consistent in most urban large scale cities is you will always find yourself waiting for one thing or another; be it the train, a bus or a cab; standing in a grocery line or Post Office; waiting at the Motor Vehicle or for a movie to start—those are all opportunities to write or revise your work.  Use a note pad, your smart phone writing application or voice recorder or even embed your words into an email, there is always time to write, even in New York.

General Resources

Who Needs an MFA When You Have Free or Inexpensive Workshops

New York Book & Literature Festivals

Places to Jam & Listen

Yes, I said Meet In-Person! NYC Writers

When Membership Pays

  • Author’s Guild (sliding scale based on your writing salary)  Note: Once you are a member you receive invitations to panels and programs throughout the year. NETWORKING!!
  • Writing Rooms (Rent 24hour accesses spaces to write by yourself or with others)

Ok, Maybe You Do Want To Get Your MFA

Need a Space to Write

Most of us have no choice but to write wherever and whenever we can. And should we be lucky enough to find a little free time and a secluded spot, life still has a habit of interfering. Now I’ve seen it all, desktop computers with full 22 inch monitors in a busy Starbucks, to textbooks, bags and papers laid out across small spaces alienating both customers and café owners. In the end, finding a good spot to write takes exploration, consideration, good etiquette and thinking outside of the box.

You should be looking for:

  1. Location (Near transportation)
  2. Service (Laid back with inexpensive but good food)
  3. Atmosphere (Ample lighting and good seating)
  4. Wi-Fi & Electrical Outlets
  5. Extended hours of operation
  6. Amount of Traffic: (You don’t want to take up space and potential revenue for long periods of time, so find the best places and times to go to a particular café to avoid these kinds of issues)

FREE (Wi-Fi & Seating)

SPENDING $4-$6 For the Space, Outlet, and Wi-Fi

SPENDING $10-$25

$400 and Up

General Hot Spots

Natasha is an aspiring writer living in New York. You can follow Natasha’s writing adventures on Twitter @GirlWriter and on her blog.

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