|Sam (Jared Padalecki) and Dean (Jensen Ackles)|
As a long time fan of the show, when I think of the names Sam and Dean I can't help but associate them with strength and masculinity. Another nice little touch I love in the show is that Dean is named after his maternal grandmother, Deana, and Sam after his maternal grandfather, Samuel. It's nice to see writers putting a little thought into how these 'loner' boys are connected to that side of their family, despite their mothers tragic death when Sam was an infant.
Beyond the first names of the various characters on this show and the actors who play them, the name that has perhaps caught my fancy the most is Winchester. We already have names such as Colt (#330 in the US in 2011!), Smith (of Smith & Wesson), Gunner, Hunter and Cannon, so I think this is fast becoming a very usable name. As a first name, you have the nickname possibilities of Winn or Chester, or if you feel the gun association is too strong this could make a masculine middle. For those that like their names with a touch of olde worlde British charm, this also has a sound reminiscent of other British locations such Rochester. In fact, Winchester is an Old English word meaning 'Venta's Village'.
For those not convinced by the idea of a Winchester in the family, here are a few other suggestions inspired by the characters of 'Supernatural':
Castiel (made the nn Cass cool for men)