Walking into Starbucks, a medium golden blonde, grizzled man in basketball shorts and a black Legend of The Seagullmen shirt waves me down. When approached, Jack Gregory looks like he’s already set to call it a night from his exhausted look.

It’s been a normal workday for him: networking, correspondences, working on a client sketch, and watching the results of an illustration he made during a rare bit of downtime get reposted all over social media.

The viral illustration is something Gregory drew out that’s inspired from the upcoming Joker movie. The image features a punched out glass mirror reflecting Joaquin Phoenix’s portrayal of the infamous DC villain flashing a sinister open mouth smile across five shards. Like the character’s persona, it’s visceral and conjures a sense of both danger and excitement leading up to this movie’s release.

For Gregory, that’s the motive with his work. “How can I convey the desired reaction with as little work as possible and make something stimulating within everyone’s deadline, all with having people not swipe through in two seconds.” The statement’s second part is also a fear of his that he circumvents through in each piece he does.

Gregory’s career in the visual arts spans 15 years, short by his standard, however that time frame has seen him work on thousands [sic] projects ranging from art direction, digital marketing, key art for film and television, traditional painting, and alt movie posters/gig posters. The latter being something he’s made a name for himself in the past few years with his work with Off! to as recent as Rancid, Hank Von Hell, L7, Descendents, Against Me!, and a slew of others artists alongside movie poster recreations of The Great Escape, Halloween, and Apocalypse Now amongst others.

Gregory looks tired during our meeting, but there’s a noticeable aura of confidence coming from him. Amongst small talk, Gregory mentions a personal accomplishment worth mentioning. “I’ve finally accepted that I’m good at what I do. I have pride in my job, I’m not a wallflower at meetings, and I’m very present.” Amongst his humble and professional nature, he’s very ambitious and driven by his capabilities and believes his best work lies ahead of him. Gregory reflects upon his past self and work to where he is today, “God, I had delusions of grandeur when I finished school. 21 years old and I’m going to take the illustration world by storm and immediately work the biggest names. The notion that I’m not alone; there are thousands of others in my position who are way better and have practical, real-world experience with the know-how didn’t register with me then. It was total arrogance on my part. I look back at my work now and see all the errors honestly, my work when I was 21 is laughably bad. I can confidently say I’ve come a long way since.”

How so? “A combination of getting better at your craft and skill, do the work. Also, network and market yourself, which is something I didn’t put any effort in early on.”

Like every artist, he got to this point from somewhere. Gregory, an Indianapolis transplant in Los Angeles, came to the West Coast via an agency job offer in 2011. Since the move, he’s steadily built a reputation and a diverse portfolio which has made him a sought out illustrator within the world of the entertainment industry. As he mentioned, it wasn’t a stroke of luck that got him to this point; it was a realization that he didn’t know how to market himself effectively towards his interests. He took action to solve this, sought feedback and advice, applies it, consistently. Gregory credits a few key points in his life, something that is accessible to everyone, for starting him out and is crucial for sustainment in this business.

  1. Web Presence: “I have to credit two agency guys I interviewed with back home who gave me the best long term and practical advice for all this. Eight or nine years ago when I was still in Indianapolis, I didn’t have a grasp on how to use social media. I was arrogant, figuring my skills themselves would get over the top of the pile and garner me an audience. I’d create images, post them on my blog, and leave them there, not even attempt to get them out in any other means or channels. I’ll never forget this job interview I had with an agency for a job designing email send-outs for a shampoo company. These two guys that brought me in literally told me, “After seeing your portfolio, we understand you. You’re not some 70-year-old man who doesn’t give a shit anymore; you don’t know how to market yourself.” I sat there for 45 minutes taking everything they said in like get social media going for yourself, get a website, network like a bastard every day. At the time, left that interview bummed because I needed the job (laughs) but looking retrospectively, I needed to hear all that, and guess what, it works, I wouldn’t have gotten specific gigs if it wasn’t for Instagram.”
  2. Networking: “Another thing they said was to get the fuck out of Indianapolis, which I was fine on hearing. I made a FB and Twitter account for my artwork and let it grow from there. Every day, the first two hours of my day was networking like a fiend looking for work, I didn’t care about the relocation part. Whether it was Durham, Portland (Maine and Oregon) I was sending my resume and portfolio to any graphic design or illustration job in the hopes of picking up some freelance work or someone taking a chance on me. Luckily, there was a company in Venice who saw my work and arranged a Skype interview. They gave me a test project to do, and it passed, that’s how I got out here.”
  3. Social Media: “Once I moved to Los Angeles, I had my full-time job, which I learned a lot from and am grateful to still work with as a freelancer. Even though I was gainfully employed, I still have my ambitions and dreams to work on gig posters cause I grew up listening to rock and punk bands and wanted to participate somehow. I’m not a musician, so being a visual artist was my way in. Using Facebook and Instagram, I’d check the tour dates of bands I liked to see if they had any shows scheduled in Los Angeles and pitch them directly on an idea. I’d get a couple of bites from people who showed interest but the first band to say “yes, do something for us” was the band Off! For a gig, they had in 2013 at The Fonda Theatre. So, through them, I did my first legit “I have to get these printed” gig poster. Once that image got out, people dug it and then other bands started contacting me to work on their stuff. So, again, thank social media for all those opportunities.”
  4. Adaptation: “Eventually, the freelancer offers were getting substantial to the point where I bit the bullet and left the day job to take on these projects full time. That’s when the reality of the situation hit me; I need to hustle and network more all while hitting my deadlines with quality work. What I was already doing, the intensity increased 10x, and I adapted.” 

It’s a straightforward strategy; Gregory even uses KISS as a template. “You hear all the stories about how KISS isn’t the greatest band ever but in reality, they were marketing fiends dating back to the days when they were carrying their own gear, they were always on it, and you have to do that if you want to last in any industry.” 

Gregory’s very aware of his capabilities and his skill set depth. He also admits he’s still searching for what it is he likes to do. He’s very adamant on one thing; he doesn’t want to be known as a one-trick pony with a specialization in one style that his career will be remembered by. It’s actually a big fear of his. “I’ve heard of instances where successful illustrators fall into this trap; they’ll create something like a paint look and get hired by a client based upon the look. When they submit their request in a pen and ink, the client pushes back and says, “no, we want your paint look, that’s why we hired you.” It’s a reason I keep up with the latest techniques and incorporate other styles in my portfolio. Diversity is the goal, it’s why I have paint, comic, and some Bauhaus looking work there, I don’t want to pigeonhole myself to one style.”

He furthers his worries as an artist. “Being successful based upon a specific era is something I’m avoiding too. I want to be relevant, irrelevancy is a big fear of mine, and I feel most artists would feel the same way. Don’t get me wrong, I love the work of Bob Peak, but the heavily airbrushed Excalibur poster he did for that movie makes you immediately think the 1980s. That image is awesome, totally has the feel to a T. I don’t want to get to the point of success through where people are like, “Oh, in that decade, he was the man.” That’s a thought that scares me and why I continuously study other styles and artists.”

Gregory’s earliest interest in his work stems from his father, a visual artist for the Indianapolis VA hospital, who drew comic strips and is a cartoonist himself. “My father was helpful without being forceful. My earliest memories I recall are of him at the drafting table of our house; he was always working on drawings of characters or his strips. Literally, by five years old, I knew I wanted to do the same thing, and he played a direct influence. We’d talk about our favorite artists throughout the years, I’d bounce guys like Todd McFarlane and Jim Lee to him, and he’d tell me about John Romita and Jack Kirby. Also, he had a library of books that I would reference, through those I learned about classical periods like the Renaissance to names like Jack Davis, Norman Rockwell, and Frank Frazetta. I cherish that a lot and when I went to college it was bittersweet because he was very proud of me, but he’s also a very competitive guy. I would make a design and photoshop an image of myself in there, and he would do the same to counter me, it just steamrolled from there.”

Painting being his primary focus in school, he’s since branched into other techniques and mediums, notably the collectible world of music and movie poster art.  His most recent piece in that realm was for the debut US tour of ex-Turbonegro frontman, turned solo artist Hank Von Hell. One look at it, and it’s clear, like Hank’s music career, it’s a little eccentric like Gregory aimed it to be.

“Look at it. He’s ripping a monster’s heart out! This totally suits Hank and his music career, which I love! I had to go over the top with this one. His music career is over the top as is his frontman abilities. I had the time to put some extra effort into this one, and the response has been cool to see. Grandiose violence is hilarious to me. It’s totally over the top. I wish I had the time for the Sistine Chapel for my work, but that’s unrealistic. I’m glad this came out the way it did, and he was into it.”

As for the medium itself and most images being designed for an online presence on a mass level, his feelings towards the future of the gig poster and the advancements surrounding it are sound. “Nah, I can’t see gig posters going anywhere, they’re going to be relevant for years in part to the artist community behind them along with the collector’s market. The manufacturing techniques and abilities have gotten a lot better but even more so, these images being produced these days by many artists are absolutely beautiful. I mean, I see poster images on my Instagram feed that look like they belong in a fine arts gallery. It shows the artists behind them are very in touch with the band and the encompassing subject manner.”

Mentioning earlier that he believes his best work is ahead of him (being also very content and happy with where he is), Gregory still holds on to a goal set at age 15. “I want to do a Pearl Jam poster, that’s my dream along with doing something for Metallica.”

Finally, when addressing the question of what he wishes people who have no background in the arts would understand, he’s very frank. “Generating ideas and putting them to paper is more time consuming than a person thinks. The research, composition layout, the lines, finding an appropriate color, it all takes time, and that’s just the prep. Even on a computer that still applies, I think people have a misconstrued concept that the process speeds up exponentially cause of Photoshop. Also, people have a great need for the visual arts but not always the finances to back it up. I remember early in my career seeing postings on Deviant Art with a request asking for six character designs illustrated in a big battle scene with a budget of $15. And I see all these people throwing themselves at that posting with “Check out my work, here’s my portfolio” and it pissed me off because it’s devaluing everyone across the board. The original poster should have added two more zeros to the right and then come back to talk.”

Facts of life by Jack Gregory, there you go. For more info, visit his official website.

Write A Comment