A Drawing of Roger Sterling of Mad Men

Posted on by JG
Roger Sterling art by John Garrett
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Time for another Mad Men drawing, guys. This time it’s Roger Sterling, the lovable, lecherous head honcho at Sterling Cooper Draper Price.

Roger’s the guy that always has something interesting to say, and always has a drink in his hands. Or I should say he has a drink in one hand and the other hand on some secretary’s ass.

I used a frame from the show where Roger was particularly drunk as reference to draw this up.

I think in the show Roger is really starting to feel his mortality. He’s watching Don Draper, a guy in the prime of his life, getting all the accolades and all the rewards that Roger was probably used to when he was the man back in the day.

His relationship with Joan Holloway is something that turned from a salacious sort of “god this is so gross” to a “wow this is really humanizing Roger” sort of thing.

I actually think Joan is the only woman that Roger respects, so it’s kind of a shame the way things have worked out so far. For those of you who haven’t been watching this show do yourself a favor and pick it up!

Catch up on the first four seasons before it comes back this summer.

Ok this one is gonna be strange. Those of you who don’t know, Roger Sterling has a book out, called Sterling’s Gold: Wit and Wisdom of an Ad Man.

What’s strange is that, even though this is my affiliate link (meaning I get paid if you buy from this link), I’m not gonna suggest that you buy it.

This book is really only for super-obsessive fans. I picked it up and I have to admit I was a bit disappointed. It’s just a list of Roger quotes from the show.

If you were hoping for some Roger backstory (ie more of the exposition we heard on the show) then you’ll end up as disappointed as I was. It’s my own fault, though. I even read the description of the book and I still got my hopes up.

Well that enough on Roger for now. I’ll say again if you haven’t watched the show then go pick up those DVD’s, bittorrent it or something. Do what you gotta do, but check it out.

Here’s my raw pencil art of Roger (I debut these on my Facebook page so head over there and Like the page to see this stuff early):

Roger Sterling pencil art by John Garrett
Click to view larger
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5 thoughts on “A Drawing of Roger Sterling of Mad Men”

  1. Ima big fan of Roger…cool painting too…and I LOOOOOOVEEE Joan Holloway …did I mention I love her…yup…..LOOOOOVEEEE Joan Holloway …I mean…she’s ok :-p

    1. Oh yeah, Dino. Yeah Joan is aiight, I suppose. I mean she *could* be a bit better looking, I guess.

      but seriously, I love me some Joan, too! That woman is something else. I’m doing another drawing of her because my first one didn’t work out so well,so stay tuned for that.

      Thanks for commenting!

  2. Another stunner. Raw talent! Really amazing, John.

    I don’t know if I’ve fanned your Facebook page or not, so I will head over there and add you as a favorite.

    1. Thanks, Tia, I’ve been working hard to do the show justice. Now I can’t decide if I should do Pete next or my re-draw of Joan.

      Hey that’s right, we can actually “Like” the pages as our page now, right? It’s gonna be a busy weekend!

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