Artist - Diane Dempsey

We have had the opportunity to make a connection with Diane Dempsey. She is the Designer/Illustrator and Business owner of  RetroChristmasCardCompany.com + RetroLifestyleCompany.com

While she creates ALL of the fun retro images, her hubby runs the business side.

We did a Q & A email interview with her. Take a look at what she has to offer for your Christmas theme this year. 

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Diane Dempsey - Q & A

Q. For our Readers, which state do you live in?

A. Florida

Q. Where did you grow up?

A. Maryland + Florida

Q. Did you travel a lot and which images were created as a result of your travels?

A. Only Time Travel that takes me back to the Good Ol' Days.

Q. How did you become interested in art licensing to jigsaw puzzles in the first place?

A. I am actively seeking Art Licensing partners for the art I created for RetroChristmasCardCompany.com + RetroLifestyleCompany.com. It was back in 2020 during Covid that I learned about the newly refreshed interest in Puzzling. I sought out someone to print puzzles for us wholesale and instead was offered my first licensing agreement with Cobble Hill. I was thrilled! It has been a great relationship.

Q. What kind of education do you have that gives you the abilities to be so creative in your artwork?

A. As far as background on my education / experience, I am a graduate of the Ringling College of Art + Design with certificates in both Graphic Design + Illustration. I was a full time Art Director/Graphic Designer in advertising agencies from 1982 - 1993. During this time I was also the Art Director for the Cabbage Patch Kids. A few years of transition and I started my own boutique style ad agency. My clients included many of the "blockbuster" Museum exhibitions of the time and I became a bit of a specialist in exhibition/museum promotions, as well as others. 

My husband and I started the Retro Christmas Card Company in 2004. It was a on a whim - a fun hobby that grew into our vocation. We now work year round on The Retro Christmas product line, as well as The Retro Lifestyle Company "spin off" site together. We also have Amazon and Etsy shops in addition to our own websites.

Q. What products other than jigsaw puzzles have you licensed your artwork to?

A. I have licensed illustration for both Christmas and year round for many products including: Jigsaw Puzzles, Gift Bags, Christmas Decor, Coffee Mugs, Stationery products, stickers and more.

Q. Does photography enter into your work?

A. I sometimes use photography to gather reference for my illustrations. I also photograph the Retro Christmas Village Displays after they are produced for the images on our website.

Q. Is your artwork digitally enhanced or hand-painted?

A. The artwork begins as a pencil sketch that is then fully rendered in vector based digital illustration.

Q. Were you from an artistic family background?

A. My Mother was a very creative seamstress.

Q. Have you always identified yourself as an artist?

A. Yes, from a very early age.

Q. Do you know how many puzzle images you have licensed over the years?

A. All of my puzzle titles can be seen here:  Cobble Hill - Diane Dempsey

Q. Out of all your licensed images, do you know which image has sold the most puzzles?

A. I do not know as they are constantly being reprinted, it is an evolving process.

Q. This is a big ask....do you have ONE favourite?

A. So far, Vintage Main Street. This is based on the best selling Retro Christmas Cards found here: https://www.retrochristmascardcompany.com/product-category/christmas-cards/

It is also available as wall art on my RetroLifestyleCompnay.com site: https://retrolifestylecompany.com/product-category/christmas-wall-decor/

Q. If a person was interested in doing the same work you do, what is the best advice you can give them?

A. Get an education that qualifies you as a professional artist. There is much to know about the business of art, it's a blessing to do what I love for a living but one must know the professional in's and outs.

Q. Do you have a specific art studio or work from your home?

A. I have a studio at my home.

Q. Can you share something personal about yourself to us that is not on your social media channels - like perhaps 'you do jigsaw puzzles'? Or besides painting, do you have another hobby? Or maybe you know a famous person personally?

A. I am a fledging gardener, and my husband (and business manager) and I swing dance on occasion. We're old Lindy Hoppers. ;)

Q. We would also like to see/know how your 'work in progress' happens - are there images/stages that you can share?

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© Diane Dempsey/All rights reserved

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To the left and above are sample works of art fully before its is rendered in vector based digital illustration. 

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Click the above Facebook icon to open the Retro Christmas Card Company Facebook Page.


Diane Dempsey on Social Media & Shopping

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We Have an Amazon shop that will ship to Canada here: https://tinyurl.com/58trwpar


Mid-Century Modern Christmas House 
Table Top Displays

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Mid-Century Modern Christmas Cards

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Vintage Main Street Jigsaw Puzzle Review

Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″
Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″


Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″


Overall Experience:  Great

Cut Quality: Great

Board Quality: Firm

Shape Cut: random

Image Quality: Great

Hardest Area: The 2 vehicles

Puzzle Dust? minimal

Finish Quality: Smooth matte

Box Quality: Good and solid

Sealed Pieces Inside Box: no

Was this purchased new? no

Price: Picked for review

Recommend Level: Highly 

Time: 10 hours

Vintage Main Street Puzzle Assembly

I have switched up from using foam boards for sorting. Since I have established that the Grateful House jigsaw puzzling trays can hold a 1000 piece puzzle laid out, (using the lid for the border pieces) I find it convenient to layout my sorting process as shown in the images. I set up the 8 trays plus the lid and the box of puzzle pieces in the centre to sort according to colours or details. I do the border on my foam board working area first so I can put the lid on the trays for movement.

Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″
Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″

These puzzles come with a very nice quality poster as you can see in the image below and shown with the border completed below.

Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″

Using the Poster to assist with the border, it assembled quite quickly. The upper sky and the road on the bottom were fairly easy to distinguish. Then the radish colour along the left side, made the right side easy to arrange the pieces into those directions.

Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″

I started off with the light soft greens and the bigger store names to help identify areas that could be easily be assembled. The sun and Santa was a given ;)

Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″

I continued to gather little pockets of color to put clusters of details together.  There was enough detail to get about two-thirds of the puzzle assembled which left the tricky areas being the two vehicles.  They were done last but they were not too difficult once I looked closer at the details.

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Vintage Main Street Puzzle Comments

I seemed to get through this one faster than I thought I might.  I really do LOVE assembling Christmas jigsaw puzzles and have several completed by different Brands. One of my most favourite Christmas puzzles is by Cobble Hill puzzles too and it's titled Holiday Candy  - it sure was challenging to assemble and I do put it on my wall every Christmas as a form of decorations. 

I am very lucky to review jigsaw puzzles for Cobble Hill so imagine how happy I was to have the opportunity to assemble the  Christmas Camper by Diane Dempsey too. You can see my review here.

I also want to mention how nice the matte finish is on the Cobble Hill puzzles. They are non glare images and they feel so nice when my hands do the 'once-over' upon completion of the puzzles. You can see the nice random cut and quality in the close up images below.

Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″
Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″
Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″
Brand: Cobble Hill Puzzle Company

Title:  Vintage Main Street Puzzle

Artist: Diane Dempsey

Pieces: 1000

Size:  48.9 x 67.6cm or 19.25 x 26.625″

About the Artist Diane Dempsey

Diane-Dempsey-profile© Diane Dempsey/All rights reserved


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We have collected a massive list of jigsaw puzzles in numerous categories on our Amazon Store link. It's a quick way to browse most current puzzles and/or specific seasons, accessories and themes. Makes for a terrific one-stop jigsaw puzzle gift giving shopping centre. CLICK HERE