Whimsy in Every Stroke: The Joyful World of Cathy Nolan Art

Step into a world where art is more than just visuals—a celebration of connection, joy, and the magic in everyday life. Cathy Nolan has enchanted audiences for over three decades with her playful, heartfelt creations, transforming ordinary moments into unforgettable memories. From personalised portraits to vibrant caricatures at high-profile events, her work radiates warmth and humour, leaving a lasting impression. Based in New York City, Cathy’s bold lines, expressive characters, and dynamic energy have made her a favourite among global brands and local communities. Welcome to Cathy Nolan Art, where every stroke tells a story and every moment becomes a masterpiece.

Cathy, can you tell us more about the moment you took that dare at a county fair? How did that week shape your perspective on art and lead to a lifelong career?

The minute I accepted the dare, it was as if the universe and the stars all aligned.
I had enough money to pay the fee for my booth, my grandfather’s orange Buick car to drive back and forth to the fair, a table and chairs loaned from a friend and the art supplies.
While getting people to come to my booth I learned that people are very self-conscious about their looks and being drawn. Many hesitated to sit down with me so I guaranteed them that if they did not like the drawing, they did not have to pay for it. That sales technique worked very well because I was able to persuade people to come and sit down, ask them questions about their lives, hobbies and interests and incorporate that into the artwork. Many people would get so busy talking to me that they forgot they were being drawn!

By the end of that week, I had grossed over $1000 as an 18-year-old kid and realized that I could make a living drawing people at festivals and events. So that kickstarted my career as an artist. I participated in many street festivals in Chicago and learned a lot about running a business, networking and marketing way before the days of social media and the internet! I realized I had a gift and that it was meant to be shared by bringing joy to many in this world. A few years later I moved to New York City and the rest is history.

Your art style is so warm, expressive, and full of personality. How did you develop this unique style over the years, and what inspires its evolution? 

I have been drawing since I was 18 months old and was fortunate enough for my mother to recognize my talent at such a young age. I drew on library books, walls and just about anything to express myself using crayons, markers and pencils. I guess my unique style came from within me and from years of practice of drawing, studying art and creating every single day. I made a promise to myself at a young age that when I grew up, I would continue to draw. The art of drawing and creating is how I express myself and it’s evolved. 

With such an impressive range of clients, from major corporations to personal commissions, how do you tailor your approach to capture each client’s unique essence? 

My approach is to find out first the client’s objectives and then I ask myself how can I best help them meet those objectives. What does their brand stand for? Their colors? Their essence? What is the story behind them and their brand? The more information or research that I do on a client then the better the essence I can capture for them. 

Your art radiates joy and connection. What do you think it is about caricature and live drawing that resonates so deeply with people? 

I feel like a caricature or live drawing of someone is like a mirror – looking at a version of themselves in an artistic format. I believe we are all connected and my mission is to bring joy to each person whom I draw so that they can look at the image I created of them and see the beauty and essence of their being. Art does bring joy to so many and it’s something that I think people resonate with on an emotional and spiritual level.

Do you have a particular project or event that stands out as a turning point in your career or that holds a special place in your heart?

One event that stands out to me as a turning point in my career was working for ABC News in the heart of Times Square, New York City for the 2016 National Election. I had drawn a caricature of Hillary Clinton and Donald Trump on paper. I would ask voters who they were voting for and why, and they would be “drawn” to their favourite politician. Hearing their reasons why and their stories as I drew voters was fascinating and fun for me.  A friend of mine visited me from Singapore and we were standing on the FaceBook electronic platform. She said to me, “Cathy. Look at all of this. How many artists can say they are a part of this?!” That is when it hit me that wow. This was a huge moment for me. I was telecasted on Livestream and briefly featured on the show Nightline. 

It’s inspiring to see how you share not only your artwork but also your creative process on social media. How has this openness impacted your art and your relationship with your audience?

I love my audience and appreciate them so much. I feel that the more open one is with one’s life or process in creating something, the more one can inspire others to do the same. Sometimes by showing someone what is possible, that encourages them and gives them hope that they can also trust their own creativity and get inspired to create as well. 

What are some of the biggest challenges and rewards of creating art live at events? Do you have any memorable or surprising experiences from these sessions?

The reward of creating art live at events is seeing people’s reactions when you present them with the artwork. Many will smile and laugh, others will be moved and touched and others will be like “Really? Does this look like me?” A caricature is the artist’s interpretation of how one looks and I try to capture the true essence of the person. One of the biggest challenges I have had is making sure my digital printer works when I am booked to draw digital caricatures! A surprising experience I once had was being hired by a company called PitchBook for their holiday party. I was scheduled to draw for only three hours but this one man insisted that I stayed on for an extra two hours. I didn’t know who he was but I told him that I had to check with my client to make sure it was okay due to budget. Then he told me “I AM THE Chief Financial Officer. Trust me. You can stay!” Well that was enough assurance that I was approved to stay for an extra few hours! He was paying my paycheck!  

You’ve worked with high-profile clients and major brands. How do you ensure that your artwork captures both the brand’s identity and your signature touch?

I get very curious about my subjects and always do my homework beforehand. I study the brand, its mission, its colours and its essence and research the person to find out more about their life, their work and why. Then I sit and ask God / Divine source for guidance on what to illustrate. The first idea that pops into my head is the best one to implement. For example, I had just heard Candace Bushnell, the author of Sex and The City speak at an event. Then I found out she was doing a one-woman show the following week. So, I did some research on her and found out that when she sold the television rights it was a pretty bad deal for her and a toxic situation. A lot of creators get screwed over when they sell the rights of their creations to the Hollywood industry. No one foresaw that the show would be so successful and she did not get paid what she deserved in royalties etc from the show’s success. So I am asking myself, what can I create to bring some joy for her? What can I draw that would be a reminder that her creation validated all of this success? I mean, there would have been NO SHOW if she had never written the book in the first place. So I had this vision of her thinking of creating her main characters: Samantha, Miranda, Charlotte and Carrie with a pencil in her hand as a writer and a published book in the other. When I presented the artwork to her, she loved it! I like having my artwork be a reminder to people that they do matter, they are seen and valued by just being who they are. 

Your work often celebrates everyday moments and relationships. How do you go about capturing the essence of a person or a scene in just a few strokes?

Honestly, I don’t know. My talent is so innate and I just capture the essence of that person through the pen and see what comes out onto the paper. I absorb and observe their energy and try to create that in a drawing. I feel it comes from years of experience and practice and being willing to show up and do the work when it is called at that moment. 

For those who look up to you and might want to follow a similar path, what advice would you give aspiring artists looking to turn their passion into a career?

Nurture your gift. Tap into your creativity. Draw and doodle a little bit every day. Dream big and never give up on them. Start small by creating for your friends and family members and gift them that piece of artwork. Ask them to tell everyone whom they know that you are selling your work. Ask for clients and you will receive them.  You’ll never know if you don’t ask. Look into trade shows, and craft shows, post your work online and just show up.  Just do it. Your gifts are meant to be shared with the world. If anyone needs encouragement or cheering on, then reach out to me at [email protected].