Rob Tobolsky is not one to keep still. A bit of a rolling stone, he’s had a number of varied and successful careers. Tobolsky took a minute to chat with me about his latest venture at Blokes Barbershop & Gentleman’s Emporium and how he discovered life outside of Philadelphia. Some responses have been edited for length and clarity.
So what part of the city are you from?
I grew up in South Philly down by the stadium. I grew up in the house my grandparents grew up in, in traditional South Philly. My great-grandparents were the original owners. Later, my mom and dad bought it, and I grew up there.
Were you close enough to hear noise from the stadiums?
Yes, we would sit in the backyard and watch the fireworks at the vet stadium. It was cool.
What did your folks do?
My mom has worked for the School District of Philadelphia since I was nine. She started as a cafeteria worker, and now she’s a manager. My parents divorced when I was nine, so my mom got the job when they split. My dad was a professional musician, so he would play weekly gigs at bars and restaurants. After they had kids, they needed more money and insurance, so he took a job at a place called Disc Makers and he worked there for 10 years. When I was 15, he moved to Virginia and he’s been down there ever since.
Years ago, I put out a CD for kids with alternative families, and I had it made at Disc Makers!
That’s really funny. Yeah, if you wanted to make a CD, he was the first call. You probably spoke to him.
Small world. What kind of things were you into as a kid?
I was really into cars. I was the kid who had 1,000 Matchbox Cars all lined up in our living room. We also did a lot of outdoor stuff. It’s funny. Neither of my parents grew up in the city. My mom grew up in Media, where I live now and my dad was from Cherry Hill. They bought a starter home in South Philly and never left. But we never went out in the city at all. We always went out to places like Linvilla Orchards or my dad would take us fishing, camping and hiking. So even though we lived in the city, we spent way less time in town than we did outside of the city.
I understand that your grandfather is somebody you were close to.
Yeah. The house I live in now was my grandparents’ house. It’s very special to me because my grandfather, my mom’s dad, was like my father. Even before my dad moved to Virginia, we just saw him on the weekends. After he moved down there, we’d see him twice a year. We talked on the phone but it wasn’t the same. But my grandfather was present through my entire high-school and teenage years. He did everything for us. He would take us on adventures. He’d be like, “You want to go for a drive to Lancaster?” He’d come pick us up and we would just go. He was a rock and we were very close.
Is he the one who taught you gardening?
That is correct. I went into horticulture because of him. Every summer, I’d come and help him with his garden. And I thought, “This is the coolest thing ever, and it’s what I want to go to school for.” So I went to Saul High School in Roxborough. It’s that really big farm up on Henry Avenue. It’s the only functional farm in Philadelphia — acres and acres of farmland and it’s a high school! It was the coolest experience and he inspired me to go. People are always like, “I hated high school.” I loved it. We were working in the greenhouses. I took classes like ornamental cultural design. It was really cool. We participated in big competitions. It was a blast.
I would imagine you did the flower show too.
I did the flower show and the farm show. It was great. And I would never have considered it. He was the one who was like, “You are great in the garden. Why don’t you try to apply to Saul?”
Do you remember what your best exhibit was?
Oh gosh. It was so long ago. I remember one funny thing though. We were doing the PA Farm Show, and we wanted to do an exhibit about Fairmount Park. We wanted to show that there’s a really beautiful spot in the city that people don’t know about. But there was no budget for plants, for flowers, for soil, for anything. So we went into Fairmount Park with a wheelbarrow, dug up some shrubs, and brought them with us to the farm show in Harrisburg. We kept him alive for the week, brought them back, replanted them, and no one ever knew the difference.
What did you do after high school?
I was already working at a flower shop on South Street. I was the assistant manager there at 19 years old and was like “I don’t need to go to college. I’m doing fine.” I got my first apartment in West Philly. It was great. And then six months later, I got laid off in the flower shop and I was like, “Well shit. What am I gonna do now?” I applied for other florist jobs, but they wanted me to start over again at the bottom. I ended up moving back home and thought, “Maybe I should do hair.”
Why hair?
In high school, my friends and I didn’t have enough money to get the haircuts we wanted. So we learned how to do it ourselves. I ended up being pretty good at it. So when the flower shop job went bust, I went to beauty school. I’m not the kind of person to just sit around. I don’t like being stagnant. When one opportunity ends, I have to find the next thing. I signed up at the Jean Madeline school.
You started off by cutting your friend’s hair. Was it nerve wracking, like the first time you cut somebody’s hair?
No, I didn’t care. We were all just weird, punky teenagers. What’s the worst that’s gonna happen? We shave our heads? It didn’t matter.
That makes sense.
I was more nervous when I started doing hair professionally in the salons and my family started coming to me. The first time my aunt came to me to color her hair was nerve wracking, but everything was fine.
And I read you later switched professions again!
[Laughing] Yes! So I did hair for five years. In 2013, I stopped. I was just over it. I’m the kind of person who exhausts all my options before I give up. I worked Supercuts. I worked in a really high-end mainline salon. I worked for the punky salon on South Street. I did all the versions of hair I could do.
I was 20 years old, and at first I thought, “I love it here in Philadelphia. I’m gonna get an apartment. I’m gonna live in the city, do hair, and that was it.” Then I started dating a guy who was in the architecture program at Temple. He did a study abroad in Rome and invited me to visit. So my first flight ever was to Rome in 2012, and it opened the floodgates for me. I was like, “Oh, traveling is really cool. This is too awesome. I don’t want to stop.”
And something during that trip got in my head, because in the next couple of months, I ended up quitting my job at one of my salons, moving twice, like something was off with me. I was getting anxious and depressed, and doing things that weren’t great for my health. I was not good to myself, it was really bad. By December of that same year, I thought, “I need to stop. I’m being destructive and I need to change something.”
On a whim, I decided that I was going to move to Portland, Oregon. I don’t know why. Honestly, I think it was the year that show “Portlandia” came out and I thought, “That seems like a cool place.” I got it in my mind that it was utopia, and I wanted to go. So I packed my car up and left. My original plan was to be on the road for a week and a half. I ended up being on the road for six weeks.
I went to Atlanta, New Orleans, Austin, Phoenix, Grand Canyon, Las Vegas — I went everywhere across the country. It took me out of Philadelphia for the first time ever, (besides going to Italy) and it changed my life. It took me out of my comfort zone, and I saw so many different ways of life that I didn’t know existed. I was used to Philadelphia and the same four bars we always went to, and thought that was life. But when you leave the East Coast, it’s very different. I met awesome people along the way. I camped in my car. I slept on beaches. It was like, “What could happen?”
Well, probably a few things!
Well, yeah, there were a few times where I was like, “Oh my God. What did I get myself into?” I had a flat tire on top of a mountain road with no cell phone reception. I couldn’t get my tire off and was stuck for five hours. But I made it to Portland and it ended up being almost the utopia I thought was gonna be, especially the queer community there. It was so different from Philadelphia. In Portland, they didn’t care who you were or what you looked like. I was never a skinny little thing going to Woody’s dancing on the blocks. In Portland, it was like “No, you don’t have to listen to Lady Gaga. You can like Kate Bush and have a good time.” They really embraced the alternative and I could be whoever I want to be. So I spent the summer there, and then when I ran out of money, I came home to Philly. I wanted to keep traveling so I applied to every airline around and I got hired by Spirit Airlines. I became a flight attendant and did it for nine years.
What place surprised you?
I never thought of Germany as a cool place to visit. But Munich ended up being this very relaxed, beautiful city with an eclectic, diverse community. The people were just so cool it ended up being one of my favorite cities to go back to.
What’s the farthest you’ve traveled?
The farthest I ever traveled was Japan. I got to go for two weeks and that was really, really cool.
How was coming out for you?
I never really realized who I was until my teenage years. I knew as a kid that I wasn’t this typical, “I want to get married and have a wife and kids” person, but I didn’t know what I was. Middle school was awful for me. I was in the same class of 30 or 40 people from kindergarten through eighth grade. It was not a good experience. I don’t really have many memories of back then, because I shut them out. There was relentless teasing and bullying. I would go to the bathroom and cry. I think I had one friend during my entire time. So I didn’t allow myself to explore who I was, because I was being told by everyone else what I was, in a bad way.
Transferring to Saul made all the difference. I got to meet people who I never would have ever experienced living in South Philly. I started to realize more of who I was in high school, and with my new friends, I opened up. Like, I’ll never forget my freshman year, I got invited to go watch a movie with some of them. It was “The Rocky Horror Picture Show” and I’d never seen, or experienced, anything like that. My parents were very liberal. They’re open to everything but there was never anyone who was different around us.
What was your first dating experience?
I was talking to this guy online. We talked for maybe six months or so, and then decided to meet up. Thankfully, he was the same person in his pictures and he was my age — no catfishing. I told him I didn’t know what I was. Maybe I was bisexual, maybe pansexual, I didn’t know. Then he gave me a hug, and I was like, “Oh, this is different. This feels different from anything else I’ve ever experienced in my life. Wow, OK.”
And I slowly explored more into myself and realized, “Ok, I do like guys.” I was never in the closet. I just didn’t know who I was, and then I finally figured it out. The first friend I ever told was my best friend, Cheyenne. The guy I met online ended up breaking my heart and I called her crying, “I’ve had this awful thing happen, blah, blah and he broke up with me.” And she goes, “Whoa, whoa, did you say he broke up with you.” I said, “Yes.” She goes, “Oh, OK.” And that was it. And then slowly, I just started talking about it with everyone.
So let’s talk about what you’re doing now at Blokes. What makes the place special, and what do you do there?
Well, what I do there is transforming every day. I was originally hired as a part-time front-desk person, and I started taking on more and more responsibilities. And after being there for six months or so, I decided that I wanted to do hair again. I never saw myself doing hair again, thought I was burnt out, but I have never worked in a place where I felt so comfortable. The owners, the clientele, the barbers — the shop just feels like home. And I’ve never worked for people who are so aligned in the same way of thinking with our politics, our morals, everything. They go out of their way to make everyone feel included and special and welcome. And that was an experience that was new for me. They ask things like, “What would make you feel more comfortable working here?” They care. They really do. When I told the owner Duke that I wanted to do hair again, he helped me get my license back. He trained with me for four or five months getting my skills back up again. Now I’m a barber and the manager of the shop.
Fantastic! So let me just ask a few random questions. So in your time with the airline, did you ever see snakes on a plane, or any odd emotional support animals?
There was a monkey once. That was weird. It was cute though. It just kind of sat and ate snacks, and was very calm. We had a guy try and sneak his dog with five puppies onto the plane. That was bad. Animals that are still nursing are not allowed to fly. We had a chinchilla once. And it was not emotional support. It was just someone trying to sneak a chinchilla through.
Do you ever have those “Queer Eye” moments where somebody says, “I want to have this done” and you’re like, “No, no, honey.”
[Laughing] All the time! I have no problem telling you no. I mean if you come in with jet-black hair and are like, “I want it to be white blonde,” Sorry, it’s not gonna happen.
What’s the wildest ‘do you’ve done?
When I worked on South Street, I was able to do some fun stuff, special effects colors, like vivid purple, and blues. I did a bright green pixie cut that was pretty cool. Like Joker green colored. I love doing things that are just a little bit different. At the barber shop, we don’t get too out there, but I’ve had a few cool mullets. I want to make my mark as a barber, but not traditional. Getting into that now at Blokes has been so rewarding. You can go to somebody else for that traditional fade. I’ll do the other stuff.
Any celebrity encounters?
I had Flavor Flav on a flight from Vegas to Chicago.It was a red eye and he was sleeping. I walked past and was like, no, no way. So I checked the manifest, and I’m like, “That’s him.”
Are you more poolside or beach side?
Poolside for sure. I don’t like the sand.
If you could do anybody’s hair. Who would be the ultimate choice?
I want to say Stevie Nicks, but I’d be too terrified. She’s my favorite singer. And Harry Styles. I think he always has such cool hair.
What’s the oldest piece of clothing that you own?
I have a bin of clothes I just pulled out because of Halloween. Do you remember the club Shampoo? On Wednesday, they used to have a goth night called Nocturne. From the ages of about 18 to 22, I was there almost every Wednesday. It was my home. It was my scene. I had a whole drawer of goth clothes, which is now a small bin that lives under my bed. I’ve had them since I was 16 and some of them still fit! Including these crazy lip-service pants with like leather flames on them. I’ll occasionally bring them out for random club nights that don’t happen much anymore.
A favorite saying or line?
Before she was in Fleetwood Mac, Stevie Nicks was a cleaning lady. She has a lyric, “I don’t want to be a cleaning lady. I want to be a star.” That always resonated with me. For me, it means, “I always want to do something a little bit better, to take the next level.”