A 5th Grade Punch to the Gut & Hillary Clinton

I've been aching to sit down (and complete) a caricature recently...I do love me a good caricature.

Speaking of which, I've got a good story about the first (and last) time I ever tried to use my drawing wares to pick up a lady. It was fifth grade and I had a crush on a girl named Angie - cute, blond curly hair, middle school cheerleader who was 'going with' the quarterback. I sat at her homeroom desk, which was full of pink Trapper Keepers, during 4th period English. I thought that if I drew a funny picture of her boyfriend Jason and discretely placed it inside the desk...she would find it the next morning, fall deeply and helplessly in love with me and immediately dump him in favor of me. So, I scratched out my best caricature of her boyfriend eating dog poo on a sandwich bun (which I cleverly accompanied with an arrow and the words 'dog turd'). I was quite happy with the likeness...I even included his football number on his shirt. With a huge sense of satisfaction, I placed my masterpiece in her desk and daydreamed about future hand holding in the hallway.

Flash forward to the next day at recess. Here comes Angie...walking right toward me with a huge smile on her sweet, little face. The plan had worked out perfectly! That was, until Jason came out of nowhere - punched me in the stomach, and said 'That's for drawing pictures of me!' Angie turned around, grabbed Jason's hand, and together they walked to the other end of the playground.

I cried.

I cried again a few weeks later when a girl punched me - but that wasn't art related.

So, back to the caricature. Seeing as how the eyes of the world will be on Indiana this Tuesday for the big Obama / Clinton showdown - I wanted to take a stab at Hillary. She's a master of contorting her face, so I thought it would be challenging and fun.

Here's the initial sketch (Painter) :

Not sure about that...it was close, but maybe a bit too young.? When I went into color, I tried to angle her up a bit more, emphasize her age and the very impressive bags under her eyes.

Hillary Clinton (Photoshop / Painter):

Her expression reminds me of the feeling I had after my 5th grade beatdown. Foreshadowing? We'll see.