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This post is long..if you just want to see finished pics, click here.)
Last month a neighbor approached me with plans for a Christmas project he was doing. He wanted to make a gift for his family of the game "Guess Who" but using their own faces as the characters in the game! He would put the game together, he just needed someone to do the cartoons of his family: 11 siblings, their spouses, and the parents.
I thought it sounded like a great idea, but I protested that cartoons of real people aren't really my specialty. He kept insisting though, and after much flattery I consented to do some sketches to see if it was what he'd like. Besides, I had some new expensive markers I bought last summer, and I hadn't done anything with them yet!
He gave me a family portrait of all the siblings for me to look at, and this was the example page I gave him after a few hours of sketching:

I had to wait a few days before he and I were able to get together to discuss it. When we finally spoke again, he said he loved them and thought they looked like his family, but he'd like to see a "more finished" version of the drawings before he decided.
I wasn't quite sure what he meant , except maybe to have a more definite square background, and less pen? I had made some observations about the real game piece proportions (of which he'd kindly given me a copy) and emailed a few times asking what he wanted me to do about shapes and sizes. He answered that he still needed to see a more finished piece before we could discuss specifics, because he wanted to be sure I could make what he wanted.
So these are the next few I finished. I especially liked the mom:


When we were able to talk again, he said he liked them, and was ready to move forward. He gave me a list of three family members and the specifics they wanted for the drawings, including eye color, background colors, shirt colors, earings, lipstick, and even facial expressions!
I totally understood needing a limited choice of colors to make the game better, but I was having a hard time with the specific expressions thing- he wanted to reflect each person's personality, which was a great idea...unfortunately, some of them didn't have the desired facial expression in the photo reference, and I'd just be making it up out of my head. I was worried about getting too far away from how they really look.
My neighbor sent me a few more pictures of the three people so I had more references (always helpful!) and I was about to get started when I was told to hold off on the colors as he was going to poll them about their favorite colors!
It was great he was going to so much trouble to personalize his family's gift, I was just worried about the time factor-time for me to finish all of these drawings, and time for him to put 12 games together! Although they are small, I can usually only get two to three done in a day, around my other daily obligations. So I pressed forward with the info I had:



As you may have noticed, each of them has a faint square border around the person. This was a template I'd printed from the computer, just to help me make all of them approximately the same size. I figured when I did the larger background later the lines would be covered up by the colors.
Finally, I was given a chart with all the specifics for every person, as well as more current photos of everyone involved. I was glad for this, because several of the people had changed quite a bit since the original sibling portrait had been taken! I was also glad to see the chart wasn't as complicated as I feared- no facial expressions, and the backgrounds were now to be plain white. This is probably what we should have done from the beginning...but now I couldn't use the previous three sketches because of the squares on them.
Oh well, at least I got lots of practice before the real thing, right?
Once I got started with all the final details in hand, this project was much more enjoyable! I just wish I'd known all the specifics from the beginning.
So, for cartoons, you should exaggerate features and add less detail than a realistic portrait. I sometimes struggled with these two things and had to remind myself constantly to make eyes bigger and stop drawing so many detailed lines in the hair,etc. I also somehow drew them larger on each page, but I'm hoping it won't be a problem since they'll be shrinking them anyway.
Some of these turned out very close to the real thing, while others were not so great. So these are the (almost) final 24 drawings:





This is the mom again; I felt the earlier drawing looked more like her but I'm not good at duplicating the same thing over again, so oh well.







I hate how that line to the side of her mouth got smudged...this looks a lot like her, so I don't want to do it over again!

This guy was Hispanic, but I didn't want to use a different skin color because it would make the game too easy. I decided to just outline his features in a darker color.

The color was weird on this scan, but he's really the same as the rest. Also, I had finished the drawing when I received a recent photo that showed him with a goatee (he just had a mustache before). Luckily, it wasn't hard to add.

There were several women in the family with this same haircut and color, which is great for the game but I was worried they'd all look exactly the same as a drawing! I hope I made them different enough.




I love that there was more than one example of every style, from goatees to bald heads; their game should turn out great!





There were two that didn't look quite right to my neighbor, mostly because the photos I had of them were too small and I couldn't see the details well. He offered to pay for the new ones, but I redid those two at no charge:


Lessons learned from this art project:
- Pen and Marker are not nearly as forgiving as pencils; I didn't include the several portraits that were almost done then I got pen in the wrong place or smeared it.
- Be prepared for projects to take a LOT longer than you think they will.
- Make sure you have all the details before you start working on it!
I was also reminded why I haven't actually pursued illustration at this point- that field is all about pleasing someone else and following their directions, and repeatedly redrawing the same thing over and over till they're happy! I'd much rather have a general idea and then be handed the reigns. But this was a great learning experience for sure!