DJ Ray works his magic. (Photo courtesy DJ Ray O & Son Entertainment)
Ray Ouillette listens to a lot of different genres of music. Pop. Hip-hop. Rock. Country. Soul. R&B. Standards.
He likes them all, but when it comes to listening to them, he really doesn’t have a choice. It’s his job. He has to play all of the above if that’s what folks want to hear.
“I play just about everything from today’s top 40 to all the past hits in just about every generational era from the 1950s to present,” Ray said.
DJ Ray O & Son Entertainment (more on that name later) is Dracut Economic Development’s Business of the Month for June 2025, which is appropriate as June is National DJ Month.
“When I’m doing a job, the goal is to make sure everyone leaves the event happy,” Ray said. “I want people to say, ‘Wow, I had a good time, I wonder who that DJ was.’”
Ray started playing tunes for folks at the old Club Fleur de Lis (now The Sandbar Beach Club & Grill) on Long Pond on the Dracut-Tyngsborough line in the late 1990s, when he was about 18.
“I started going there and being in awe of the DJ, who I became good friends with and, ultimately, my DJ mentor Chris Perez,” he said. “I fell in love with the idea of playing music and making people happ.”
He eventually branched out from Fleur de Lis to take on events – birthday parties, Jack-and-Jills, reunions – all the while building up his arsenal, not just of material, but also of equipment.
“I started gathering equipment. I started off with small, low-end stuff. But I have assembled quite an inventory of equipment, anything from audio to lighting,” he said.
Building a side hustle
Ray worked in customer service until Covid came along, at which point he started working for Dracut-based DTE Construction while his wife, Angela, stayed at her full-time job. The construction job gives Ray more flexibility to practice his “side hustle” of getting people onto the dance floor.
DJ Ray O and son, RJ, at the Old Home Day 5K race. (Photo courtesy DJ Ray O & Son Entertainment)
“I’m very fortunate to have employment with a company that understands work/family life balance and that gets my outside passion for music,” Ray said.
Ray grew up in the Navy Yard neighborhood and now lives in Collinsville with Angela and their three kids – Ray Jr. (or RJ), 18, Sadie, 14, and Paisley, 8.
“I have always loved Dracut, love being a hometown boy,” he said. “These are my roots. It’s where I want to be.”
When preparing for a gig, he likes to go in cold, with no preconceived notions of what songs he’ll play.
“I don’t make a play list,” he said. “I’ve got to gauge the crowd and read the people. You can tell if they’re vibing to it. I’m throwing things at the wall to see if it sticks, and when you find it what’s working, you stick with it. That’s when I know I’ve got them.
“You have to be able to pivot. The atmosphere can change. It’s dependent on the people in the room. They will tell you what direction to go. Body language shows, head bobbing to the music, feet tapping, etc.
Ray Ouillette of DJ Ray O & Son Entertainment is ready to go. (Photo courtesy DJ Ray O & Son Entertainment)
“I pride myself on trying to hit every genre. Everyone’s musical taste is different. You can’t go from Frank Sinatra to hip-hop. You have to gradually make your way. I’m taking people on a musical journey with endless stops.”
In 2021, Ray started DJ’ing the 5K road race at Dracut Old Home Day. In 2026, he hopes to take over the main DJ gig at the gazebo for the annual event as regular DJ Mark Watson is planning on scaling back after this year’s Old Home Day on September 6.
DJ Ray O & Son Entertainment has hosted events at just about every Dracut public school, as well as the old Franco-American School, Lowell Catholic and, just recently, his debut for St. Michael’s School in Dracut at Harmony Hall.
Killing it
He has performed at various town recreation and sports events and other community events.
“I’m very proud to be a part of this community, and anytime I can be involved makes it that much more special to me,” he said.
“I finally did an event for Saint Michael’s, and I killed it. I love it when people say to me, ‘You were just what we wanted.’”
When he says he “killed it,” don’t worry. Ray will also tell you when he botches an event.
“I’m my own biggest critic,” he said. “No one is going to criticize me more than me. I look at the dance floor as my canvas and the people as my paint. If the dance floor isn’t full, I’m feeling a little disappointed.
“I have bad nights, nights I feel off. It’s a bad feeling. I don’t go to events thinking, ‘I can’t wait to stink out the place.’ I always feel like I could do better. I’m ending the night going home and thinking, ‘I wish I had played that one song, or done this a little differently”
While the events he works run the gamut, his favorite is birthday parties, what he calls his “bread and butter,” because everyone’s happy and just wants to dance and have fun.
“People always want to dance to ‘Macarena,’ ‘Cotton-Eyed Joe,’ ‘Hot in Herre’ by Nelly, ‘Play That Funky Music,’ ‘Cupid Shuffle’ and your other party staples,” he said.
For other events, like reunions, the music has to be a little more subdued because people are there to talk and reminisce.
He doesn’t do many weddings because couples often have a do-not-play list – songs they absolutely do not want to hear. But then comes the DJ’s dilemma: What if a lot of people at the wedding do want to hear those songs? Ray likes to have what he calls “creative control.”
“If a bride and groom say, ‘Don’t play this song,’ but all the people are requesting that song, I’m playing it,” he said, “because those people are going to tell the bride and groom, ‘Hey, he didn’t play this song we all requested,’ and the bride and groom aren’t going to say, ‘We told him not to play it.’ It’s going to be on the DJ.
“I’m very transparent with the clients when it comes to those types of situations.”
He said working various events is “like going to a job interview for the next booking. You don’t know who’s listening, or who might be looking for a DJ.”
Hit the road, Jack
No matter who’s listening, DJ Ray O tries to end every event with the same song, Ray Charles’ “Hit the Road, Jack.” It’s kind of his signature, letting everyone know the party’s over.
So, about the name, DJ Ray O & Son Entertainment. While Ray does have a son, RJ isn’t planning on following in dad’s DJ footsteps. So what’s with the name?
“For my 30th birthday, my wife had a party for me,” Ray said. “My son was just about to turn 1 at the time, and my wife had a banner made that said, ‘DJ Ray O & Son Entertainment.’ So I just kept the name.”
And 17 years later, the name lives on. Just don’t expect to see Ray with an assistant. He’s a one-man show. “No overhead so I can provide quality services and keep the prices affordable.”
“I’m not doing this to get rich,” he added. “Music is my vice. It keeps me grounded. It makes me happy to make other people happy and enjoy themselves even just a few hours to let their hair down, get away from the everyday grind of reality. Rest assured, when I show up, I’m bringing the beats, and I’m going to give you everything I have.”
And with that, it’s time to hit the road, Jack.
For information on DJ Ray O & Son Entertainment, email daddydj615@comcast.net or follow on Facebook.
