Behind the Scenes of DoodleTown with Reuben Award-Winner Dave Whamond and the Team at Cobble Hill

We’re thrilled to share that artist Dave Whamond, the creative force behind our wildly popular DoodleTown puzzles, has once again been nominated for the prestigious National Cartoonists Society Reuben Award in the category of Advertising and Product Illustration and the winner will be announced on August 15th, in Boston, MA. And yes, the product is of course a DoodleTown puzzle. Yay! Not that we wouldn’t cheer him on if it was for any of his many other achievements because he has in fact won Reubens in several other categories. His portfolio includes illustrations for Wall Street Journal, McDonald's, the "Oddrey" book series, and so much more!

Curious how someone dreams up these delightfully chaotic cartoon scenes? We asked Dave Whamond some questions to find out. And because it takes a village to build a DoodleTown, we also sat down with the owner of Cobble Hill, David Manga, and the creative-loving Art Director, Chantal, who helps bring the DoodleTown madness to life.

The Birth of DoodleTown

CH: Where does the name DoodleTown come from?

David Manga, owner: We picked the name a long long long time ago. All the original DoodleTown images were city scenes, and the art looked kinda “doodle-ly”.  Hence the name “DoodleTown”.

CH: How did you come to meet Dave Whamond? And what about his work made you think that it would make a great puzzle line?

David Manga, owner:  I actually first came across Dave Whamond on a website that links artists with people looking for creative talent.  What I loved about the work he had posted was his attention to the little things. When you are assembling a puzzle you are closely looking at every little piece. Which means we want puzzle imagery that has lots going on. Dave is so creative and funny with all the vignettes. I didn’t even know he was Canadian at the time – that is an added bonus!

CH: How many Reuben Award nominations and wins have you received to date in 2025 and what were they for?

Dave Whamond, artist: I have been nominated around 20 times and have been fortunate to have won 8 Silver Reubens. They were for Book Illustration, Advertising and Product Illustration, Newspaper and Magazine Illustration. 

Note: You can view more of Dave's work on his website, here: https://davewhamond.com/

Building a Puzzle World

CH: How do you strike the right balance between visual chaos and puzzle-friendliness with these funny and chaotic scenes?

Chantal, Art Director: That’s a great question! We always start by creating the scene that will contain all the characters. We structure it with a clear foreground, middle ground, and background. We often include a main element to help ground the image; like the camper in “Call of the Wild” or the barn in “Farmyard Folly”. 

We make sure to have enough variety of zones to allow for the different vignettes to visually flow throughout the image. For example, “Birdwatcher’s Paradise” has a marsh, a path, grassy patches, trees, and an info lodge to offer a variety of spaces. Then Dave starts to populate the scene with our best ideas. A lot of moving around ensues as more ideas and characters are added. Paying attention to colour blocking also helps to create visual balance.

CH: How do you determine what theme(s) will be next in the series?

David Manga, owner: Of course, the subject matter needs to be popular enough that lots of people will want to assemble a puzzle with that particular subject matter. But the subject also has to lend itself to having lots of fun things going on. Take for example "Birdwatcher’s Paradise". We know bird puzzles are popular, but just think of all the shenanigans that can happen when people are out in nature looking for birds. What really makes a DoodleTown image a DoodleTown image is all those funny interactions.

CH: You’ve been creating your internationally syndicated cartoon Reality Check since 1995. What are some of the biggest challenges, joys, or differences when creating a cartoon scene for a jigsaw puzzle compared to a single-panel?

Dave Whamond, artist: A single panel comic can be more challenging as you need to get an idea across in a simple image with the least amount of words possible. It had to communicate immediately. A puzzle is much more involved but really, the same rules apply. In a puzzle scene, there are a whole bunch of funny scenarios that need to be depicted in a simple way so you can see what is happening at first glance. A lot of artists tell me they could never do the larger detailed scenes but I really enjoy them. You can just throw yourself into the scene you are creating. Sometimes, you get so into it, you can even discover the meaning of life. Okay, maybe I'm exaggerating a bit but you kind of just get into the zone and you are in your own little world.

Favourites and Funnies

CH: What is your favourite DoodleTown puzzle image thus far and why?

David Manga, owner: My favourite DoodleTown image so far is Viking Voyage. Why? Because who doesn’t want to be a Viking sailing the open seas in search of new lands and adventure. There is so much fun stuff happening in this image.

"Viking Voyage" is available in Family Pieces 350 and 1000 pieces

CH: What is your favourite DoodleTown puzzle image thus far and why?  

Dave Whamond, artist: It is difficult to choose just one but I think I enjoyed working on the bookstore puzzle the most. It's probably because I love bookstores and as I was drawing it, I imagined myself walking around in there. I wanted to live in that space!   

Chantal, Art Director: It’s the same answer for both of us — “Bookshop Bedlam” because we both love books (and I love cats)! "Bookshop Bedlam" was created as an exclusive for Barnes & Noble. Indoor images are more challenging in creating enough spaces for all the character vignettes. But we figured it out, and created a cozy space that we’d each love to hang out in — though maybe without some of the chaos! It was initially rather monochromatic, but once we added bright hits of colour everywhere, the whole bookshop sprung to life. When it’s available to all retailers, you’ll be able to find the picnic gang again, reading in the corner with the kids and their dragon puppeteer…

Win a copy of "Bookshop Bedlam"!
Details at the end of this interview!

CH: Do you have any favourite ‘aha!’ moments or running jokes that have made their way into the puzzles?

Chantal, Art Director: My all-time favourite character is a baby raccoon eating candy in front of “Haunted House”. At the same time, we were working on “Call of the Wild” where a picnic gang with a raccoon, rabbit, and squirrel made it onto the camper’s roof. From there, the gang has continued to make appearances from a ‘tee time’ within “Par for the Course” to braving the high seas on a raft in “Viking Voyage”, among others. Dave’s raccoons are my favourites.

Collaboration and Creative Process

CH: average, how long does the creative process take from conception to approving final art to send to press?

Chantal, Art Director: It’s difficult to say exactly how long these take, as Dave and I both focus on DoodleTowns between other work due to the projects’ scope, and all the back-and-forth involved. As you can imagine, as fast as he is, Dave’s artwork takes some time, and my feedback for each round takes time, too. The first part of the process involves researching the theme, and brainstorming ideas and possible image layouts. From there, he creates the setting through various sketches until we have a world that we are happy with, and finally moves on to a clean drawing. The next stage is populating the world with all the characters and jokes. This involves a lot of back-and-forth, re-jigging, moving about, changing and adding ideas. The final stage is adding in all the colour. At this point, while most of the image is set, we continue to adjust and move things about. There is less back-and-forth at this point. Lastly, I do a final go-through and clean-up, then move on to the press files. Then we start all over again with a new theme! I like to set aside about four months to feel comfortable with the timeline and balancing other projects, but we usually get each done in about three months.

CH: What has it been like seeing your cartoon style come to life in DoodleTown, especially knowing puzzlers are spending hours poring over every tiny detail?

Dave Whamond, artist: I have had many puzzlers tell me that they love the detail in the puzzles. So I keep that in mind when I'm working on it. My style for the puzzles has also evolved over the years. I used to do the puzzles traditionally with ink and watercolour, which made the large artwork a challenge to scan and also much more difficult if we have to make revisions. I now do the puzzles digitally with a program that can mimic watercolour quite well. I draw them traditionally, then scan them and add the colour and details digitally. I also have most of the characters on separate layers so we can move them around and resize them if needed. A lot more work but it gives us more options as we are working on it.

CH: What do you enjoy the most about collaborating with Dave Whamond?

Chantal, Art Director: Dave is fun and easy to work with. He speedily creates full worlds based on our brainstorms, populated with whimsical interactions, in his signature style. Puzzles are a different beast to book and editorial illustration. He is patient with my attention-to-detail requests in our effort to offer an exceptional experience for our puzzlers. Dave and I share a similar sense of humour and imagination, and collaborative spirit, which makes us a great team.

CH: We’ve read that many of your ideas come from hours of research on Google and your own imagination. But does any of your DoodleTown art draw from your own personal or real life experiences that you've witnessed? We're thinking Thanksgiving Togetherness or Call of the Wild!

Dave Whamond, artist: Yes, I think a lot of my work incorporates my personal life. Even if I'm on vacation, the brain doesn't shut off. You're always taking things in and there are always funny situations happening around you. In fact, I have real life cartoon characters working for me every day. It's funny you mention those two puzzles as I threw in a few things from my camping and family dinner experiences. 

The Future and Career Advice

CH: What advice would you give to young or aspiring cartoonists who want to develop their own voice and maybe even turn it into a career like you have? Do you have any memories about when you first started doodling or fond memories of your first published cartoon?

Dave Whamond, artist: I started drawing as soon as I could hold a pen. My parents realized my passion early so they would hang giant rolls of newsprint in our hallway. I would fill it up with drawings, then they would take it down and hang new paper and I would fill it again. I didn't realize you could actually make a living doing what you loved until I heard about art college. So I went to the Alberta College of Art and Design in Calgary (now University Arts) for a 4 year program in Visual Communication.

I HIGHLY recommend going to a good art college. You may think you can draw well but it will make you see things with a new eye and improve your skills immensely. You will also meet 'your people' there. People who are interested in the same things you are and you feed and learn off of each other.

If I could recommend another thing for a young person just starting out, I would say keep drawing! There will be a lot of road blocks and times where things might seem like you will have to give up the dream, but keep believing in yourself. Think like a business person (yes, artists and business sometimes don't mix but make it work for you) and find a way to get your work out there so you can keep pursuing your passion.

My first cartoon was published in the Edmonton Journal when I was about 8 or 9. It was for a feature called The Cartoon Bug and it was a forum for kids to submit their own cartoon. Once I saw my drawing in print, in an actual newspaper that everyone reads, I was hooked! I still get a bit of a kick when I see my work in print or online. It's kind of in your blood. 

CH: What drives you to continue adding to the DoodleTown collection?

David Manga, owner: DoodleTown images are the type of puzzles I personally like to assemble. So the drive to make more images is somewhat a personal interest. I want to see what other everyday activities can be turned into great puzzles. Our newest image being released soon is called "Offside Antics", which is a funny afternoon soccer game in the park. Just watching how the image evolved was  a great pleasure. (We can't wait to share "Offside Antics" with you - thanks for reading our interview)!

How to win a copy of "Bookshop Bedlam"

Good things come in pairs! We’re giving away a copy of DoodleTown: Bookshop Bedlam plus another Cobble Hill puzzle of your choice!

How to Enter:
Tell us which DoodleTown puzzle scene you would like to "jump into" and why! Leave your comment below or on our pinned DoodleTown image on Instagram or Facebook during the contest period.

Deadline to Enter:
All entries must be submitted by Thursday, June 5 at 11:59 PM PST.

Winner Announcement:
Two winners will be selected - one at random and one with our favourite comment. Winners will be announced around 9:00 AM PST on Friday, June 6.

Explore the DoodleTown collection:
https://www.cobblehillpuzzles.com/collections/doodle-town

Find your daily dose of Dave humour, here:
https://www.gocomics.com/realitycheck
https://cagle.com/dave-whamond/