Recently, I stumbled upon the work of Wendy Macnaughton, an illustrator and graphic journalist based in San Francisco. She has an interesting body of work--some of her pieces make you laugh, some make you think. A few make you laugh first and think later, and a couple make you think first and laugh later.
Hierarchy of Needs, New York Times
Office Hours, Dell Tech Page One
Should I Check Email, Dell & Forbes
Things Happen, 20x200
Her illustrations have appeared in the New York Times, Wall Street Journal, Time magazine, "and stuff like that."
Check out her website and her tumblr to see more of her work.