June 11th, 2008. West Hollywood, CA. Does Jay Leno look bored with his job, or what? He was out on the streets getting some interviews for the Tonight Show, but does he seem happy or even content with the idea? Not so much. Granted there could be a lot of reasons why he looks emotionless, but we think that retirement is the only thing that is going to put a smile on Jay’s face.

Do you remember when Jay Leno’s hair color was completely inverted from what it is now? It’s amazing to us that this change and maturity has happened before our eyes, and we wonder why he looks bored. Nearly half of this man’s life has been spent behind the camera, who wouldn’t be over it by now?