Interview: Jamie O’Sullivan, Portland Barber + Salonist


Jamie O’Sullivan has run his barber shop / salon on the 5th floor of the State Theater building for almost 10 years. I consider him to be a Portland fixture.

I have known about O’Sullivan and his larger group of friends since I moved to Portland back in 2001, but it wasn’t until a couple of years later that I [sort of] met him after hours at the Congress Street Denny’s. I was sitting with some friends at a table near the door and saw Jaime and another friend standing in line. Behind him were four sort of boxy, stereotypical frat guys. Two young black guys walked in and walked up to the hostess to find out how long the wait would be. Finding it too long, they left and said something like, “Eff that” on their way out. I would learn this later on, after the incident went down, but after they left one of the frat guys called them niggers and O’Sullivan spoke up. If you don’t know him, he’s a little dude, as was his friend, and I had just turned to look at the line when the racist put his hand around O’Sullivan’s throat and started to choke him while drawing back his other fist to punch O’Sullivan in the face. Without really thinking about it, I got involved, and the racist and his posse ended up leaving and the police showed up about 15 minutes too late to do anything about the situation.

Anyway, this is elemental to what I have appreciated about O’Sullivan ever since. He’s a little dude, but he’s got a lot of heart and he isn’t afraid to open his mouth. And now, about a decade after that incident, he’s my barber.

Note: I know that there is some contention about who should be referred to as a barber based on certifications, training, and so-on. O’Sullivan refers to his shop as a salon, but I call him a barber both in the title of this piece and a handful of times in the interview. While he is certainly a salonist, having done what he does for several decades now, he is certainly a barber as far as I am concerned. Take that from a guy whose father was so crazy obsessed with the importance of this distinction, he took his son to the Boston area every five weeks for haircuts by a tiny Italian man named Remo.

When did you start cutting hair?

I originally started cutting hair in high school, which was 23 years ago. There was a guy at summer camp who was a barber and he was cutting everyone’s hair with clippers. He was from Spanish Harlem and he was cutting the hair of all of these inner-city kids from Atlanta. I jumped on that bandwagon and started getting my hair cut by him. He showed me how to cut my own hair at the end of the season and I came home from camp and asked my mother to buy me a pair of clippers. I would cut the of anyone who would let me. I went into the bathroom with those clippers for the first time and came out with no hair. I got better at it over time.

When did you take it to the next level?

After I dropped out of college, I came back to Maine and I had been getting my hair cut at this place in Seattle that was this funky, unisex walk in barber shop and I dreamed of opening a place like that here, but that never happened. I got into the business, though, right around then. I was at a place called New You, and then A Cut Above, and I have been here in this shop for 9 years.

Most younger people tend to jump around in their careers, but you have stuck with this. Why do you think that is?

I am good at it. I am not the kind of person who lives to work, I definitely work to live. Doing this provides me with the money I need to enjoy my life, to hang out, go snowboarding, make music or whatever. I am good at it and this is my career.

You’re a lot more personable than any barber I have known. What do you think it is about you and your personality that makes you good at what you do?

I think that there are two different types of barber. There are those who listen to their client talk, and they are sort of a therapist. Then there is the other kind, the storyteller. This is someone who has a lot going on in their lives and that describes me. That is a big part of why people are drawn to keep coming back, I think. It is a small shop, it is just the client and me and this view of Congress St. It all adds up to this one experience which you might not get at your typical salon or barber. I do have story-teller listed on my Facebook profile. It says, “Owner, Operator, Jaime O’Sullivan Salon,” and it also has a list of what I do and story-teller is at the top of the list.

Certainly not everyone wants to hear every little personal story you have, and it can be something I struggle with sometimes… [Laughs] You know, to keep my mouth shut. But I am also the kind of person who wears my heart on my sleeve.

You must really get to know people over time.

Absolutely. Absolutely. I didn’t realize this at the beginning, but yeah, you really get to form a bond with people. What is really special is getting to know peoples’ kids. I always wanted to be a dad, but I probably am not going to have children of their own and I have known some of these kids since they were three years old and now there is one kid in particular who has come in all of his life and he is 16 now. I will know him when he goes to college, and I will probably know him when he comes back from break. You form these lifelong friendships and it is so wonderful to be able to watch people grow up.

Alex Steed

About Alex Steed

Alex Steed has written about and engaged in politics since he was an insufferable teenager. He has run for the Statehouse and produced a successful web series. He now runs a content firm called Knack Factory with two guys who are a lot more talented than himself.