Joe met Sidewalk Dennis, a Boston Common chalk artist, on a sunny April afternoon as we were walking along The Freedom Trail. Dennis had just started a new drawing. Late in the day as we strolled back through the park, we noticed Sidewalk Dennis standing in front of his latest finished piece – a sunset scene rimmed with daffodils in honor of the upcoming Boston Marathon and the city’s “Boston Strong” slogan.
He called Joe over with, "Hey! Would you like a picture?”
A smiling Dennis posed in front of his artwork, then told us about his mission. “I’m all about positivity. All the transit cops know me, all the police know me, even the meanest undercover cops know me.” Tapping himself on the shoulder for emphasis, Dennis added, “They all come up and pat me on the back and say, “Keep doing what you’re doing.””
People continued to stream through the park even though the wind was picking up and the sun was now hidden behind a cloudy sky. A few stopped to admire and snap photos of Dennis’ chalk drawing. Pointing to the subway station behind him, Dennis added, “I’m the only artist allowed to draw on this building. It was built in 1914 and it’s the oldest train station in America.”
Dennis’ story was interrupted by a twenty-something young man, who pointed at the chalk pieces on the cement and asked, “Can I write something?”
“Keep it to one square, please, so everyone can have a turn,” said Dennis, before adding, “I’ve met people from all fifty states and lots of countries – even Istanbul.”
We paused to watch the young man write his message out in script. With his practiced eye Dennis read the note that was upside down from our perspective, “With all my love. @dearlonelyhearts.”
Looking the young man over, Dennis pointed to his inked forearms and said, “The tattooed ones with the piercings are like me. We have sensitive hearts.”
The young man replaced the chalk, dusted off his hands, said a hurried “Thanks!” and was on his way. Dennis walked us over to another one of his drawings and pointing to a cherry tree in full bloom said, “I did this two days ago. It’s holding up pretty well.”
After giving us a moment to admire the tree, Dennis added, “I’ve never taken an art class in my life.” Holding his hand at knee level, Dennis said, “I started drawing with Sidewalk Sam when I was this high. Sam drew on the streets for about 40 years. He came to me and asked me to keep his tradition going. He went to artist heaven a few years ago.” Laughing, Dennis added, “I might be the only one crazy enough to do it.”
