Christmasy Illos of 2009 (Part Two): The Boston Phoenix Meets "Mad Men"

I'm hopelessly addicted to Matthew Weiner's wonderful AMC series Mad Men, so when Boston Phoenix Art Director Kristen Goodfriend asked in early November if I'd like to draw a Mad Men-themed cover, I felt the familiar rush of nervous excitement that accompanies every dream assignment. I can't speak for other illustrators, but when I'm asked to draw something that I love, the stakes are somehow higher. I suppose that's because in these rare instances, I'm working not just to please the art director, but also myself as a fan.

At first, Kristen said that the Mad Men cover would be part of the Phoenix's Ski Guide, although neither of us knew how they'd manage to connect the show to skiing. Fortunately, the editors soon decided that their Christmas Gift Guide cover would be more appropriate for the Mad Men treatment, and I agreed that this was a much better fit.

The series' third season finale, ("Shut The Door, Have a Seat") had just aired, bringing big changes to the show's storyline. I suggested that an impromptu Christmas party scene in the newly-reformed ad agency's hotel suite office might make a nice Gift Guide cover illo. Here's Sketch #1, (drawn in the midst of feverish coughs and sneezes, owing to a nasty flu):


Upon seeing the first sketch, Kristen's suggestions were (thankfully) both sensible and few in number. She felt the mood needed to be somewhat cheerier, (it's a Christmas party, after all). She also asked that Christina Hendricks, ("Joan Holloway") get central placement in the composition. With these changes in mind, and in a somewhat improved position in my battle with the flu bug, I drew Sketch #2, (which I think is noticeably better than Sketch #1):


Sketch #2 got the thumbs-up, and here's how the final art turned out:


And there was more.

While the group illo would run on the cover of the Gift Guide insert, Kristen also wanted some Mad Men art to run on the paper's front cover. Specifically, she asked for two standing figures that she could use to frame her cover lines. We quickly decided that Jon Hamm, ("Don Draper") and Christina Hendricks, ("Joan Holloway") were the show's most cover-worthy cast members, and here are the results:


But wait, there's still more!

Just when I thought I'd finished this job, Kristen asked if I could squeeze out one more quick illo for a short prose piece that would serve as the Gift Guide's intro. The story featured Sterling Cooper's creatives banging heads in Don Draper's office, deliberating over the best way to conjure the holiday spirit in a campaign. By this point, we had just a couple of days before this issue went to press, and I needed to keep this illo fairly simple in order to turn it around by deadline. Here's Sketch #1:


Kristen's response was: "If you can work in Peggy, (maybe on the right side?), it's a go!" I drew up a quick Peggy and pasted her in on the right, (don't let anyone tell you that I can't follow direction). Sketch #2:


And here's the final art for the intro illo:

Caricature-heavy assignments like this one usually leave me dazed and full of self-doubt. I found Jon Hamm particularly tough to draw, mainly because the guy is so god-damned handsome! Only in the last of the three illos did I arrive at a Don Draper likeness with which I was fully satisfied. I'll leave it to you folks to tell me how well I nailed down these likenesses, (please be gentle but firm).

Happy holidays!