Even though on the first one the camera's position is a bit low for my taste, I like how he appears tall, and important. The lighting and the overall exposure on that image are also done well.

Because of the high ISO, and 1/40sec exposure, looks to me that most of the light was ambient, and a little bit of flash was added to his left side to add contrast to his face.

Instead of the "most interesting man in the world" impression, because of the Playboy logo on the book, and the glass of questionable liquid, he strikes me more of the "most rebellious" type.

I actually like the second one better, but think that the glass and the book don’t' go well together. Maybe one, or another, but not both in the same shot. Good lighting on the subject on second one.

Cheers!