Google's Sergey Brin, in jogging socks and mom jeans, just looks depressed in a faceoff with the dapper Alfred P. Sloan, who turned G.M. into the world's largest corporation.
Twitter's Jack Dorsey, with the collar pop and sunglasses, is no match for G.M. kingpin Charles Stewart Mott's eyebrows and lap dog combination.
This one really isn't fair. G.M. founder Billy Durant, in his jaunty driving cap, can't help but laugh at Google founder Larry Page's unfortunate shirt.
Louis Chevrolet shows Facebook's Mark Zuckerberg that a t-shirt and fleece is not how you do casual by opting for a suit, tie, goggles, and leather driving gloves. Mustache and cigarette are optional but highly recommended.