Cory Freeman Interview

Cory Freeman hails from Central Wisconsin but has just moved to the Windy City where he will get hitched (or has got hitched, depending on when you are reading this.) Despite being unemployed, he doesn’t really understand the concept of free time. That might be the after-effect of having his mind blown when his art was selected by We Love Fine for official Star Wars merchandise.

50 Cory Freeman t-shirts on the Shirt List.

Cory likes to write and design games as well as doing t-shirt art but as this is a t-shirt site rather than a gamer or literature site I’ll just ignore those facts. Cory is indeed a fine artist so I will forgive him getting all pedantic about his educational background so he can save his energy for creating these beautiful t-shirt designs. Read the interview and more importantly, buy Cory’s t-shirts. I did mention that he is currently unemployed and about to get married. He needs all the financial and moral support he can get!

Cory Freeman Interview

I see you are based in Chicago. Born and raised?
Nope, the Chicago move is actually quite recent. My wife-to-be (we’ll be married in less than a month!) and I just moved to Chicago from Upstate New York. But we’re both originally from Central Wisconsin.


What’s the best thing about where you live?
We moved back to this area to be closer to family and friends so that proximity is definitely the best thing going for our newest home. But of course, it’s Chicago, and there’s PLENTY to do around here too. But I do miss the Italian food from NY!

What do you like to do in your free time?
Much of my free time is actually spent working. I have lots of hobbies, most notably (other than drawing/painting) fiction writing (I enjoy dabbling in both sci-fi and fantasy) and playing and designing games, both digital and table-top. When I’m able to get away from work, there’s plenty of couch time spent with my lovely lady getting caught up on whatever TV series we’ve been told to watch. But even if I’m watching TV I’m pretty much always working on projects even if only in my head.

Liam Sweeny Book Cover by Cory Freeman
Liam Sweeny Cover Design by Cory Freeman

What do you do to put food on the table?
Graphic design, in some form or another, is my bread and butter. I had been working as a book designer when we lived in NY, but I’m still in the process of trying to find something more permanent here in Chicago. Between looking for something more stable and steady, I’m just trying to get my work out there and have my fans help put food on the table. It’s very much appreciated when they do!

About the Artist

When did you start creating art?
Like most illustrators and designers, I always loved to draw as a kid. It wasn’t until high school, however, that I really started to pay attention to real artists, and started to get interested in digital art and graphic design. I bought my first Wacom tablet maybe around age 15 and I’ve been creating digital artwork ever since.

House of 64

You have a BA in Fine Arts. While your t-shirt art may be fine I don’t think it would be considered fine art. Did this help you in your career as an artist?
Actually, I technically have a Bachelor of Fine Arts (a bit more rigorous than a BA) in Graphic Design. But any good art education should be pretty general and cover a lot of bases. Though the majority of my skills and way of thinking stems from my training in Graphic Design, I always use knowledge and techniques learned from the more fine arts (drawing and painting, especially) with all of my work. I love to paint, but it’s tougher to make a living as a painter, and it just so happens that I love design too, and that’s an easier field for finding work.

Apart from t-shirts, what other art/design projects are you involved in?
As I mentioned before, one of my purest hobbies is game design. I list it as a pure hobby, as opposed to my jobby of t-shirt design, which is a hobby that is also currently my sole source of income. Anyway, game design is something that’s always fascinated me and I love pretty much every aspect of it from creating the worlds to the artwork (of course) to establishing the rules of the game. I’ve currently got a couple of projects in the works including a 2D Puzzle Platforming video game that I’ve been working on with a group of friends. I’ve also made several table-top games and I’m working on a 4-player strategy fantasy board game now.

Bag-End Sketch
Bag-End Sketch

Could you describe your typical design process from concept to completion?
I often get ideas when I’m in an inconvenient place… in the car, in the shower, trying to fall asleep at night… there’ve been more than a few times when I’ve gotten out of bed to write down an idea. If I can actually remember ideas, then I start sketching. I usually sketch digitally, but I’m just as happy with a pencil if I’m not at my workstation. Once I’ve got a low-resolution rough sketch I’m happy with, I start the process of refining it down to something worthy of scaling up. After I scale up the sketch I usually start drawing/painting final artwork and keep on refining and showing it to friends whose opinions I trust until it’s where it needs to be. Never underestimate the power of feedback from your friends. When you’ve been working intensely on a design, it’s very beneficial to get a fresh pair of eyes!

About the T-Shirts

How did you first hear about daily t-shirt sites like TeeFury and contests like WeLoveFine?
The first time I heard about a WeLoveFine contest, I hadn’t even done anything for t-shirts (other than uninteresting promotional stuff for in-house jobs). One of my good friends sent me a link to the Star Wars contest over at WeLoveFine and told me that if I didn’t submit an entry, he’d disown me as a friend.

Star Wars t-shirt by Cory Freeman

Do you remember your first t-shirt contest win? If so, what was it and how did you feel?
That first Star Wars contest at WeLoveFine turned out to also be my first win. As a monster Star Wars fan, to have a piece of mine licensed as official Star Wars merchandise was mind-blowingly cool. I often say that it was like winning the Super Bowl the first time I ever stepped foot on a football field. It was pretty awesome. I still get excited when I get a design officially licensed, of course, but there’s no beating the first time.


Of the t-shirts that you designed which is your favorite?
My Middle Earth Brews series gets a lot of positive feedback and has also been the series that’s most helped me put food on the table. As a result, it’s hard not to look favorably on those designs, and I’m especially pleased with Erebor Stout. I love dwarven culture and their visual style is super fun to work with, so that design checks a lot of boxes for me.
I’m also happy with the Gamer Crest design, as that one crashed on me about 15 hours in and I had to start from scratch. That was a bad day. But I got back in there (after taking a week to work on other projects) and redid the design from the ground up and I’m happy with how it turned out. Hooray perseverance!

Gamer Crest

Do you wear the t-shirts that you have designed?
Absolutely. It helps that I get free shirts from a lot of the printers. At this point, I would guess that the majority of my shirt collection are my own designs, and I didn’t have to pay for a lot of them. That’s a win-win, right there!

Have you seen somebody wearing one of your t-shirts in the real world?
No… not yet. I’m guessing it’s just a matter of time, but maybe I need to step it up and go to some cons or something to hedge my bets. Needless to say, I’m excited for the day I spot a design of mine in the wild like that.

Photoshop or Illustrator?
Both. Though the majority of the work I do is in PS, I use AI quite a bit when I’m up-scaling low-rez sketches, doing some vector graphics there and then going back into PS to paint over the base vector graphics. I find the software and hardware both run more quickly that way, and it allows me to let the tools kind of get out of my way and let me draw/paint more freely.

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About the World

Do you have any role models?
I don’t know if I can really name any specific one. There’s not a day that goes by when I don’t marvel at somebody’s work. I think it’s important for a designer to surround themselves with tons and tons of great work from as many different sources as possible.


What is the most exotic location you have been to?
I’ve been fortunate to have a very adventurous lady who has kept me travelling quite a bit. Perhaps the most exotic adventure we’ve taken was in Panama, where we took a very rocky dug-out motorized canoe through croc-infested waters (so we were told, but I never saw any crocodiles) to meet The Embera, an indigenous tribe. That was pretty cool.

Where would you most like to visit? Why?
Japan is pretty high on my list. I’m really fascinated by the dichotomy of the super traditional side of the culture versus the ultra cutting-edge side. Plus, though I’m not a super huge anime fan, Tokyo has that entire nerdy neighborhood which would be cool to check out. And I could live in a Japanese garden.

About Other Designers

Which t-shirt designer(s) do you admire the most?
There are a lot of really talented people out there and it’s a fairly small business. I certainly admire the talent that some of these designers have, but biggest tip of my hat has to go to designers who are able to make t-shirt design their full time job, and actually thrive off of it. It’s a tough industry to make your living by… “feast or famine” is very real in this world, so designers who can be (or appear to be, anyway) in constant FEAST MODE get major respect from me.

Collaboration between Cory Freeman & chazwik31 on Threadless

Have you done any collaborations for t-shirts?
I have indeed. I’ve got a very good friend who is an incredibly talented illustrator and I was lucky enough to convince him to tag-team a project with me. We ended up doing a very silly design featuring a rocket-shark-riding bear chasing a cat through space. It was a lot of fun working together and the end result was a design that’s actually been printed at Threadless and has gotten a lot of very positive feedback.

Who would you like to see interviewed on the Shirt List next?
How about a few choices?
DDJVigo (the brothers), Azafran, The Hookshot, Olipop, Dr. Monekers, Narwen Illustrations… there are so many 🙂


Any advice for new designers/artists?
Practice, practice, practice! Any successes that you find in the industry will come from loads and loads of hard work. And keep your eyes peeled to what’s been done and (perhaps as importantly) what hasn’t been done. There are always people more talented than you, too, so look at what they’re doing and figure out how to learn from it.


What are you watching on TV at the moment?
With the Walking Dead and Game of Thrones over for the season, new TV has been kinda quiet. But I recently took in Daredevil and I’m now getting caught up on Agents of Shield and Psych. Sometimes I’ll put on a show in the background while I’m working, so that’s a good way to have my cake and eat it too.

What’s the last movie you saw in the cinema/movie theater?
I saw Terminator Genysis in the theater… but it was merely “meh” … the last one before that was Avengers: Age of Ultron which was quite enjoyable.

Cory Freeman: Website | Facebook | Twitter


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