Chicago Tribune Holiday Cartoons

Holiday Cartoons for Chicago Tribune

Chicago Tribune needed a promotion to drive traffic to their website during the holidays. Ginett came up with the idea of a cartoon caption contest, but Tribune's editorial cartoonist was too busy with other projects. Someone needed to draw cartoons!

My Role



Ginett Colón: Art Director, Web Design

Sunny Kang: Illustration

The Elusive Santasquatch Holiday Cartoon by Katie Wasserman
Harry Hanukkah Moose Holiday Cartoon by Katie Wasserman
Festive Chicago Skyline Holiday Cartoon by Katie Wasserman
Christmas Tree Ornament Allergic Reaction Holiday Cartoon by Katie Wasserman
Gingerbread Relaxing in Teacup Jacuzzi Holiday Cartoon by Katie Wasserman
Happy Owl-idays Holiday Cartoon by Katie Wasserman
Toy Soldier Kicking a Soccerball Holiday Cartoon by Katie Wasserman
Stockings by the Fireplace Holiday Cartoon by Katie Wasserman
Aunt Edna's Festive New 'Do Holiday Cartoon by Katie Wasserman

How I Drew These Cartoons

Sunny and I looked at editorial cartoons for reference. We determined the stylistic direction for these cartoons. Simple grayscale drawings in with minimal shading. We brainstormed content ideas together. We are both weirdly imaginative, so we bounced ideas off each other and came up with some wacky ideas. We chose our favorite concepts and drew them.

I drew the cartoons directly in Adobe Illustrator with the brush tool. I created several different transparent brushes for shading. The brush strokes overlapped for a fluid texture that gave the line art some depth without overly complicating the cartoons. I drew one every day until we had enough for the promotion.

I also designed the digital ads and thumbnails to promote the caption contest on Chicago Tribune's homepage and holiday lifestyle page.

Successes and Achievements

We promoted the caption contest non-stop during the entire month of December. Ginett maintained and updated the contest landing page all through the holidays, even on Christmas and New Year's Eve. Our efforts paid off in the end with a record number of new digital subscribers. Our little contest beat other promotions that have been running for three times as long.

Lessons Learned

We got a lot of caption submissions in social media comments. Most participants are happy to submit captions, but it's an extra step to click on the link to the contest page. It's another extra step to register on Some participants that make it to this stage are hesitant to register, even with the guarantee that we don't spam.

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