Born in Dorchester and raised in Roslindale, Jack Sullivan learned the importance of the arts from the start. In the Sullivan house, TV was against the rules after school, and Jack’s mother encouraged the large Irish family to use their imagination—in the form of a few pencils, crayons, and one sheet of paper.

Through early art classes at the Holy Name grammar school, followed by a four year apprenticeship in drafting at Don Bosco Technical school, Jack was able to grasp an understanding of design and perspective, without traditional formal training and workshops. As a Correction Officer, he’s gained an even deeper perspective of human nature, despair, and redemption—and a wealth of experience that’s not always offered in traditional classrooms.

Jack then began sketching each of his five sons, and self-critiquing with the help of library-borrowed design books. Sketching then grew into paintings, watercolors, and a successful Etsy shop where customers fall in love with his serene seascapes and local landscapes.

We sat down with Jack to discuss how growing up in Boston has impacted his work and what’s next this summer. Be sure to also check out his beautiful watercolor note cards and prints, available at Cedar Grove Gardens.

What local areas in MA are you most inspired by? Are you more inspired in the summer vs. winter?
I love Summer for paintings because of the colors and places reminding me of vacation and fun.  Winter can be great if you know what you’re doing as an artist, it’s challenging because winter usually means a lot of white.  I’ve done some winter scenes I’m happy with, but I am often more drawn to summer.

You have a popular Etsy shop that ships nationally. Do you find most of your customers have roots or ties to MA?
It’s still humbling to get orders and compliments from far away places, (and local ones). Sometimes we find out people are interested in scenes they remember from long ago, but sometimes we send paintings around the world not knowing the connection or if they just simply like the painting I’ve created.

How has growing up in Boston impacted your work?
Growing up in Boston has influenced everything in my life including painting.  Lots of Boston places and things mean a lot to me and I think other people from Boston can connect with that statement.  I think Boston is a very unique place, it’s a city of neighborhoods, and families.  It’s been through a lot over the years, and it was the best place in the world to grow up.

How have other Boston artists or artists in the community supported or inspired you? Do you find that Boston has a thriving artists’ community?
Boston has an incredible history of artists. Most of my favorite artists are from Boston. J.S. Sargent is at the top of the list and Childe Hassam, born in Dorchester, whose paintings are in the greatest museums in the world, including the MFA Boston. My wife and I are lucky enough to live so close to so many legendary art places like Cape Cod, Gloucester
– Cape Ann, the coast of Maine, etc.  I love going to the local art shows and they often remind of the art fairs we used to have at Holy Name.  Even back then, I was amazed at the talent and sometimes a little surprised by the winners.

What’s next for South Shore Watercolors? Any plans to showcase your work somewhere special this summer? Any plans to expand?
We definitely need a website. Hopefully soon!

You can visit his Etsy shop here! 


  1. Sister Camille LaShnozz May 14, 2018 at 10:31 pm - Reply

    Honestly, I am quite impressed with this young man–at least he was young to me back when I was his teacher at Holy Name. I once had to go house on him when he was misbehaving in the school yard–and I do recall that blood was spilled. But what’s a bloody nose when you’re nurturing the flowers of tomorrow? I am so proud that I once called him my student. He clearly has a talent endowed by the savior himself. Godspeed!

  2. Peggy Harrison May 14, 2018 at 11:26 pm - Reply

    We love his work. Thanks for the feature

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