Jesse Smith • The Undisputed Master of New School Tattoos

I’ve admired the work of Jesse Smith for almost 2 decades. Jesse was doing some incredible tattoos already in the pre-social media era, gaining a huge recognition for his original designs. Over the years, I’ve seen tons of his tattoos in magazines and I’m super delighted to learn even more from Jesse throughout this exclusive interview! Let’s dive into the artistic journey of Jesse Smith. 

For the readers who are not familiar with you, how would you introduce yourself?
My name is Jesse Smith and I’ve been tattooing cute/evil cartoons since early ‘98.

Can you describe your artistic journey, and what initially drew you to tattooing?
Just like most artists, I have been drawing my entire life. In the beginning I spent a great deal of time copying the art from skateboard designs, garbage pail kids trading cards, MAD magazine and some Dungeons and Dragons books. These along with the advent of Video Games and 80’s Cartoons has pretty much molded my art into what it is today. In the early 90’s I moved to Heidelberg, Germany and it was there that I was first exposed to Graffiti. It was everywhere and I was obsessed. I loved the bent perspectives, crazy color palettes and its original look. It was pretty much all that I did throughout my High School years. I graduated High School in ’95 and really wanted to go to Art School. Unfortunately my family couldn’t afford to send me and none of them had ever gone to college so they really didn’t know how to guide me in that direction. Being that my father had been in the Military almost his entire adult life, he nudged me in that direction and I eventually gave in. Although I enjoyed the structure of the Army, the creative side was lacking so I found myself yearning for some sort of creative outlet. I eventually scored a job drawing caricatures at an amusement park and that exposed me to the local art scene. It was here that I stumbled across a fella named Carlos who had just been released from jail and was tattooing out of his house. I spent a lot of time at his house just drawing and hanging out. He eventually asked me if I’d like to do a tattoo. I had never thought about doing tattoos before but as an artist who loved to use any and all mediums the answer was a definitive yes. My intention was only to do a tattoo or two but after the first one, people started lining up at my front door. Not because I was good, but basically because I was pretty much doing them for free. Two tattoos turned into four and then four turned into eight.
Next thing you know I’m pretty much tattooing during any free time I might have.

How did you develop your signature New School style of tattooing?
Believe it or not, I never really sought out a signature style. I just drew things that I liked and I drew A LOT. A couple years in people started asking me about my style. Initially I just thought that they were confusing genre for style. It wasn’t until about a decade of people acknowledging my work as different that I really started to think that I actually had a style. I still to this day have issues with seeing my work from the vantage point of others.

What were the key lessons you learned while working with Bugs in London?
I worked for Bugs for about a year back in 2001. Within that time I learned a ton. A few things that I recall him pushing on, when it came to my work, were:
Backgrounds: He was really adamant about me adding backgrounds to my pieces rather than just putting stickers on people. Back then it was difficult to find artists, outside of traditional asian tattoo artists, who added backgrounds to their tattoos so I found myself studying a lot of Asian work and trying to figure out ways of incorporating it into my work. I really think that helped me figure out ways for my work to stand out.
Punctuality: Bugs was very strict when it came to punctuality. Working at his shop you were required to be set up and ready to tattoo the client at least a half hour before their appt.
Being prepared: I didn’t learn this from him while I was working for him, but when he moved out to LA I did a guest spot at his shop in Venice. I remember asking him for a roll of paper towels and was met with a pretty substantial ass chewing. He basically told me that I should show up at all conventions and guest spots prepared with absolutely everything that I needed to do what was expected from me by the client and the shop owner. From that point on I always made sure I had at least enough supplies to do my first tattoo at these locations just to feel out the vibe. If the con/guest shop offered supplies then I would, of course, utilize them. But if they didn’t I would just go get them after my first tattoo. Initially it was a pain in the ass but as I got used to it, it became comforting knowing that I had everything I need to get rolling and didn’t need to rely on anyone else for anything.
Strive for perfection: I remember him coming in and giving me shit because one of the bubbles on my tattoos was wonky. He told me that I should strive to make absolutely everything in the tattoo perfect, even if it was just a background element.
You can learn from anyone: One day I was in his room talking with him and he was drawing these tribal panthers in his style. He was struggling with one of them and asked for my advice on what it was missing. I remember thinking how awesome it was that someone with as much time in and experience as him was willing to take advice from someone as new to the game as me. I strive to carry that humbleness with me when I’m interacting with younger artists.

Can you walk us through your creative process? How do you conceptualize and execute a new tattoo design?
A lot of what I do when it comes to tattooing relies on the client. If the client has an idea as to what it is that they want then I typically have a brainstorming session with them. I ask them what all they would like and then try to figure out ways of doing it differently while simultaneously maintaining the integrity of their initial idea. If the client is very open then I’ll either talk to them about some ideas that I’ve had floating around my mind or try to nail them down a bit on things that they like that I’ve already tattooed so that I can get a feel of what it is they are looking for. Although my work may all look the same from an outsider looking in, there are a lot of nuances that I adjust depending on how I want the overall piece to feel.
When I am creating art just for myself then I typically move forward a couple of different ways.

Free Associative drawing: This is probably the funniest way to draw. I basically just start scribbling around the paper until things start to pop out.
Conceptual: When trying to create a piece that is conceptual I’ll start creating word lists and trying to find parallels and bridges between certain elements. Although this technique is not as fun, I feel like the pieces that stem from it are a lot more impactful and carry more weight.

What are some of the biggest challenges you’ve faced throughout your career, and how have you overcome them?
Ooof! I’d probably have to say the social dynamics of the tattoo world have probably been the most difficult thing for me to navigate. I came from a military family and tend to be more systematic and analytical. I find that the majority of artists don’t share that type of thought process. You accompany that with the fact that I draw differently, listen to different music and typically have different priorities than most, it creates a pretty nice cocktail for alienation. I will, however, say that as the industry has aged it’s been easier for me to find like minded people. When I first got into the industry there were very little people in the tattoo world like me.

What are some of the most rewarding aspects of being a tattoo artist?
The ability to be able to continuously create and make a living. There are very few art jobs out there where I could make a living off of doing the type of art that I do. I see artists all of the time that can draw circles around me starving because their particular industry doesn’t have as much interest from the public. And the ones who are making a living wage as an artist are typically having to create soulless work because that is what pays the bills.

What’s the most challenging aspect of being a tattoo artist in 2024?
I think that reaching your audience is a lot more difficult these days. The first 5ish years that I tattooed it was a little difficult to reach interested clients. You were at the mercy of the shop you worked at and their ability to market. Outside of that you would have to carry around a portfolio, hand out business cards, attend conventions and send your pictures to magazines in hopes that they would publish you. I feel like the golden years for me started about 10ish years in. People surfing the internet was becoming the norm and I was one of the only artists within 100’s of miles that had a site, social media was starting to gain popularity and they hadn’t implemented algorithms yet so we could reach absolutely everyone with one post and mailing lists actually worked. Around 20ish years in is where I think the tides began to start turning. Social media was slowly implementing algorithms that would stifle our ability to reach our fanbases, magazines started to die and the only way to get in front of anyone was to get on TV or do some dancing and lip sycing on tiktok. More recently I feel as though we are in that same boat but with over saturation and inflation stacked on top of it.

How did you get involved with “Ink Master,” and what impact did the show have on your career?
In 2011 they called my shop and asked me if I’d like to be on the show. Back then TV was not as widely excepted within the industry as it is today so I wasn’t really sure that I wanted to deal with the backlash. In the end, I decided to go for it. I figured if I didn’t take the opportunity then I would always wonder what it would have been like. I’m glad I did. It was a lot of fun. I met a ton of great people, learned a lot about myself, and am definitely a better artist because of it.

Being on TV shines a spotlight on, not only, all the good things that you do, but it also shines a spotlight on all of your weaknesses. As a person who strives to be the best artist that I can be, it made me work harder at tightening up those weaknesses. Overall it was a great experience and helped introduce my work to the world.

What inspired you to open Loose Screw Tattoo, and how has the shop evolved since its inception?
I opened Loose Screw Tattoo in 2011. At this point in my career I had built a pretty massive clientele and had been sending everyone who I didn’t want to tattoo or couldn’t tattoo to other local artists, so I knew that if I opened a shop I wouldn’t have any issues keeping everyone busy. This along with the urge to create a comfortable space where artists could flourish artistically led me to opening my own shop. Unfortunately, it’s never that easy. Initially my shop consisted of 4 artists in total. The shop was relatively small and in high demand. With that demand required us to hire people to handle the logistical side of things. We soon got into a place where we were turning away more clients than we were tattooing and we had maxed out the amount of revenue that we could bring in. If all the bills stayed the same and everyone was satisfied with the amount of money they were bringing in then we would have been fine.

Unfortunately I found it difficult to watch clients walk out of the door, the bills were increasing annually, the shop help wanted raises and the artists wanted higher percentages. This, of course, led to us needing to hire another artist which inevitable was the beginning of the end. The 5th artist we hired started banging the shop girl, got her to steal all of our client information and then opened a shop almost directly across the street from us. Unfortunately he managed to talk 50% of my shop into leaving with him. His wife eventually found out that he had been banging the shop girl and moved away with their son. Being a good father, he followed and now I have a shop across the street with a bunch of artists that I used to consider friends. Just like getting cheated on in a relationship, this situation made it really difficult for me to fully trust any of the new artists that I hired.

I found myself creating more rules to protect the business (and myself) from that ever happening again. Unfortunately Loose Screw has become a lot stiffer than I’d like it to be but I’m continuously trying to find that balance between running a business and creating a home for artists so that they can focus on being the best artists that they can be.

Can you describe the “Glory Hole Tattoo Booth” and the inspiration behind it?
Haha! When I first took over the Richmond Tattoo Convention in 2016 I was trying to think of ways to attract the public. My initial thought was to offer super small, free tattoos on a first come, first served basis. That idea evolved into the Glory Hole Tattoo Booth. The first year that we did it I wasn’t totally sure how people would receive it so we only did it on the Friday of the con. It ended up becoming a huge draw so we decided to make it the entire weekend. Last year we changed the name of the booth to the “Get what you Get Booth” and have added a new booth called the “Get what you Hit booth”. They’re both booths littered with a slew of tattoo designs and multiple ways to attain them for a relatively low price.

What are the biggest challenges you face when organizing the Richmond Tattoo and Arts Convention?
Running this convention is probably one of the most difficult things I’ve ever done. There are so many moving parts and building systems to simplify the overall process, without falling into a cookie cutter tattoo convention, has been one of the biggest challenges. There are lots of different platforms out there for throwing trade shows/events but they are typically very rigid and don’t have much personality. So we’ve been really focusing on building everything from scratch to try and maintain a very personal/intimate event. Another thing that has proven to be difficult is trying to throw a progressive and innovative show while simultaneously honoring our history and showing respect to the artists who have helped pave the way for the convention.

A lot of the OG’s despise the whole TV/Tik Tok tattoo world we are in today and a lot of the younger artists don’t enjoy the rough edges that typically come with OG’s. Then you have the angle of trying to make the attendees and the artists happy simultaneously at the same event. A lot of times things that will make the public happy will not jive with the artists and vice versus. So trying to ride that line has proven to be difficult.

What makes the Richmond Tattoo and Arts Convention unique compared to other conventions?
One of the things that makes the Richmond Tattoo and Arts Convention stand out from the rest is the rich history that it holds. This convention is one of the oldest conventions in the world. This year will mark 37 years since the first convention was thrown here in Richmond, VA. Since then it has housed pretty much anyone and everyone who has paved the way for where the industry is today. It is also currently being thrown in the exact same location that it started. Legends like Paul Rogers, Sailor Moses, Philadelphia Eddie and Lyle Tuttle spent a substantial amount of time at this convention in it’s earlier years.

Paul Rogers actually did his very last tattoo at this convention back in 1989. You name an artist and they were probably involved in the Richmond Convention in one way or another. Whether it was tattooing, attending or helping out. Since I’ve taken over the convention I’ve tried to come up with innovative ways of making the experience for the artists and the attendees stand out from other conventions. Ideas ranging from the “Get what you Get” booth for the attendees and creating an “Artist Concierge Booth” for the artists have been things that I’ve built from the ground up in hopes to make the experience stand out for all parties involved.

What’s your experience at tattoo conventions as a participant so far?
Throughout my 27ish years of tattooing I’ve worked a ton of tattoo conventions all over the world. I was never one of those artists who would work a convention every other weekend however I probably have worked about 2-5ish a year pretty consistently. In working these conventions I have experience everything from the small little boutique tattoo conventions all the way through to the mega tattoo conventions with 500+ booths. After attending all of the conventions I’ve always enjoyed the more boutiquey type conventions. I’ve also had the pleasure of tattooing at conventions in third world countries which has proven to be interesting :)

What advice would you give to aspiring tattoo artists looking to develop their own unique style?
Draw A LOT! I’ve been giving this same advice pretty much my entire career. The majority of artists that I meet don’t draw nearly enough. Also, make sure you’re always drawing with intention. Study other artists and how they solve certain problems that you may consistently run into. Use reference as a support but not as a crutch and take as many seminars as you can. Even seminars from artists who are doing different styles. I don’t think I’ve ever walked away from a seminar without bringing at least one nugget of new information with me.

How do you approach expanding your skill set and staying relevant in the tattoo industry?
I do all of the things that I recommended above and I’m always keeping my eyes open for inspiration. I absolutely love art and creating, so that helps.

What are some of your proudest accomplishments in your career so far?
Oh man, I don’t know. When analyzing that question I realize that I don’t particularly relish in achievements too long. When things come to fruition it definitely makes me happy but I pretty quickly move on to the next project. Actually, now that I think about it, I did get voted as one of the best tattoo artists in the world, at a tattoo convention once, along side Jeff Gogue and Nikko Hurtado. I had major imposter syndrome during that moment but none the less it was a proud moment for me. You know, another thing that just popped into my head was being included in the first “Tattoo Prodigies” book that Mike Devries put together. That book featured pretty much every tattoo artist that I respected at the time and being featured along side all of them was very humbling.

What future projects or collaborations are you most excited about?
I’ve got a side project that I’m always working on since 2009 called Carkyous. It’s essentially a fictitious continent that I created for all of my little creatures to reside. Lots of fun things are always spinning up over there. One of the projects/collaborations that I’m most excited for is this Mega Collaboration that I’ve been working on for almost 10 years now. It’s basically a 65 artist collaboration with some of the best illustrative tattoo artists in the world. I still have a little ways to go on it but I think once it’s released it’s gonna be pretty epic!

How do you balance running a business with your creative pursuits?
I don’t. I just work every day putting out the biggest fires first and then working my way down until I have a little breathing room. Then I throw a bunch of new things on my plate to create more big fires to put out. But in all seriousness, I am pretty good at prioritizing and organizing which helps out immensely. I also have a bunch of amazing people on my team.

What are some of your personal interests or hobbies outside tattooing?
I don’t do much outside of tattooing and running my businesses. I used to really enjoy Soccer, Ju Jitsu and Volleyball but after some pretty substantial injuries I’ve taken some steps back on all of that. The majority of my “free time” these days is spent hanging out with my partner and my 4 year old son.

Is there anything else you would like to tell our readers?
Keep your head up! When the world is crumbling around you, realize that everything is temporary and is constantly evolving. We will eventually land on solid ground and when we do, we will rebuild. There are a lot of disenchanted artists/people out there right now. You’re not alone. Try and focus on the things that are most important. Family/Friends, Art and Health.
The rest will fall into place!

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