Dropkick Murphys Member and KO Alum Speaks at Lunch and Lead

Tim Brennan ‘00, infamous Dropkick Murphy band member came to speak at the most recent Lunch & Lead on campus to share his story about becoming a band member, touring for over 20 years, and how his experience and the teachers at Kingswood Oxford were formative to his success. 

Brennan’s personality was genuine, down to earth, and captured the audience from the start. “It is probably rare that you get to hear about someone being in the music industry, but I can honestly say that I wouldn’t have been in the Dropkick Murphy band for the last 20 years had I not come to Kingswood,” said Brennan. “It sounds like hyperbole but it is not.” Brennan started at KO in the sixth grade. His father was also a teacher and a coach at KO so he was familiar with the community. 

Brennan shared he had always had a love for music, a passion that started when he was nine years old. After joining a local band, the first show Brennan played with them was in what is now the Leadership Center on campus. “It was the first place I played in front of people,” he said. “To say that KO played a major part in my musical career, although strange, is an absolute true fact.” 

He grew up in a family that listened to music, and a grandfather that had an affinity for traditional Irish music which Brennan was especially taken by. As a teenager, he really jumped feet first into the genre. When he was a sophomore, a young alum, Mike Marsh ’93, was hired to help fill a gap for an English teacher on maternity leave. Like Brennan, Marsh had a deeply devoted passion for music, specifically Irish music. Brennan said, “He knew I was into it so one day showed up with a tape from The Pogues, which was an Irish band that really turned it up.” Enthused Brennan, “The second I heard it it was life changing for me.” Under Marsh’s tutelage, Brennan immediately started learning how to play a range of Irish instruments. He laughed, “I didn’t think I would actually use it for anything besides impressing my friends.”

Little did he know what it would lead to. Not long after, Marsh showed up with an album Do or Die by a band called the Dropkick Murphys, their first release. Brennan was enthralled with their sound. Marsh was only at Kingswood for a year, but the impression he left on Brennan was everlasting. 

He shared that much of his success had to do with the teachers at KO. Throughout his career, the encouragement he received was ever present, and he always felt supported despite his journey looking a little different than most. Brennan laughed that he would come in with his band’s CDs and entice long time faculty members Mr. Garcia and Mr. Jones to buy them for five dollars…..which they always did. “It can’t be understated how important Kingswood was in terms of becoming a professional musician,” said Brennan. 

After graduation, he matriculated to Assumption College, in large part because of its proximity to get home on the weekends and play in his band. Brennan had a great experience at Assumption and befriended another musician who, at 18, had been asked to join the Dropkick Murphys - the very same band that had inspired Brennan to jump into the Irish music genre. His friend hadn’t forgotten that Brennan played a wide range of Irish instruments, and he told the band about Brennan’s talent. The Dropkicks asked Brennanto go on the road for three months to sell t-shirts and play accordion on stage. He jumped at the opportunity. “It was such a great experience, but tough,” he said. “It was three months on The Warp Tour where I would get up at 7:00 a.m. and get all the t-shirts out, be out all day, play a bit, then be the last one to go to bed at night. It was tough but I was just so excited about the experience.”

While those few months on the road were invaluable, at the end of the summer Brennan thanked the band for the opportunity, but announced he was heading back to school. T-shirts weren’t his goal; music was. As fate would have it, he was only back at school for three weeks during his senior year and the Dropkick Murphys called him back and asked if they would join him as a full time band member. 

Despite his obvious excitement and acceptance of their offer, Brennan admitted it wasn’t an easy decision on all fronts. “I had to make the decision to leave school my senior year, knowing what a great opportunity it was,” he said. “It was quite the gamble to take because, especially from my parent’s perspective, this was not a normal thing for their son to do.”

“Now the band doesn’t have two bigger fans in the world than my parents. They supported me, especially through the early years when we were playing at small clubs and often 22 shows in 21 days.” 

Eventually, he said, the band became famous across the world, with albums like Signed and Sealed in Blood and 11 Short Stories of Pain & Glory topping the Billboard charts, and hits like “Shipping Up to Boston” and “The Boys Are Back” which is frequently played at the Boston Garden and Fenway Park. “Shipping Up to Boston” was featured in the 2006 film The Departed and went on to become a platinum-selling single.

“It’s been quite the journey,” said Brennan humbly. “I always wanted to be a musician and I have KO to thank for a lot of that - for supporting me in what I want to do, being excited for me, and asking me to come back for things like this means the world to me.” He remarked that the support system he had through the KO community was something that was unlike anything else. Brennan played on the basketball team during his years on campus and said if he had a show Saturday night and a basketball game Saturday during the day, the basketball team would be at the show to support him.

After hearing his story, the audience, filled with students, faculty and staff, asked a wide range of questions. Many centered around where he got his inspiration for songs. He poetically responded, “Music is in the air, it's just a matter of grabbing it. You can get inspiration walking down the street or hearing something in another song that you love.” 

Brennan said the process of writing lyrics is just that - a process that you just have to do over and over. “You (most of the time) have to get the crummy stuff out before you can tap into the good stuff,” he said. “I listen to a lot of music, all different kinds, because a lot of it is immersing yourself in what you do. You aren’t going to write your best song right away. Often the first few songs we write never see the light of day. It is persistence. You can't be afraid to show it to people, and you can’t take things personally.” He shared that the original idea for the band’s arguably most well-known song, “Shipping Up to Boston,” was pulled from a song that was in the movie The Titanic. “The opening,” said Brennan, “is a combination of elements of the Jaws movie theme and what we thought would sound like something from a Tim Burton soundtrack.”

Touring with The  Dropkick Murphys allowed Brennan to see places across the globe. “I never thought that I would travel the world at all and I have been everywhere,” he said, “Getting to experience all of these cultures gives you perspective being an American in these places. You have to be super aware of how your culture comes off in other places. You learn a whole lot from that. It has been an invaluable experience to travel around the world and meet all of these people.” He also shared that while traveling has been such a gift, it can be a hard life to be on the road most of the time. He and his fellow band members often experience anxiety before they leave for a tour because they might miss and important life event with family, friends, or loved ones at home. “You just have to push through,” said Brennan. “It’s part of the job and if you let it get the best of you you would never go anywhere.”

There is no question he takes performing very seriously. “You realize how diehard people are for music and when I look out to the audience you remind yourself that this is someone's one night out to hear and see you. It really makes you appreciate what you are doing and how much people take from it.”

When asked what advice he would have for someone interested in a career in music he didn’t hesitate in his answer. “You can't get into it because you want to make money. You have to do it because you love it. Even if you do get to a point where you are recognized, there will be a decade before that where you will be playing for three people.” Brennan recalled back to the band that he played in during his Kingswood days. “There were often six people in the audience and it never occurred to us that that was the case. We were just happy to be playing. You have to just absolutely love it because there are very few pats on the back when you are coming up like that.”

He also spoke very truthfully in response to how the pandemic impacted the band. “We were so fortunate that we spent a lot of time on the road,'' said Brennan. “We are also fortunate to have good people and business managers that work for us. In the 20 years I have been with the band, I have never been home for more than a month at a time.”

“For many bands, the pandemic crushed them,” said Brennan. “We had been going so hard for so long and never taken any time off, we could afford to take that time off.” As the pandemic raged on, the band got creative. They did livestreams and virtual events (one even at Fenway Park!), and would get sponsors to help underwrite them. “Fortunately we ended up in an okay position,” said Brennan. And, he added, it was imperative he kept practicing through it all. “Music is just like any other muscle. You have to keep practicing.”

On behalf of the entire KO community, a special thank you to Tim Brennan for returning amidst a busy schedule (he leaves to go back on tour soon!) and sharing such honest and insightful words to the community through the Lunch and Lead Program in The Margaret E. and Henry R. Roberts Center for Leadership. As an integral element of our engaged liberal arts program, The Margaret E. and Henry R. Roberts Center for Leadership allows Kingswood Oxford students to fully embark on the understanding of self, others and community as we all grow as leaders. Our students are ready, knowledgeable and prepared to make an impact on our world, locally and globally with empathy and respect.
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Located in West Hartford, CT just steps from Blue Back Square, Kingswood Oxford is a private school inspiring co-ed day students in grades 6-12 with a college preparatory curriculum. Empowered students become clear confident communicators, resourceful problem-solvers, and ethical leaders. KO: where unlimited potential meets endless opportunities.
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