I'd probably take Les Stroud over Bear Grylls, but Bear is awesome too. I love those shows. As much as I'd like to take one of them, I think I'd take a hot female instead. My one item would be bug netting.
There's no point in taking a laptop with wireless internet... No ISP will have service that far out anyway.
Not to mention there is no point in bringing a laptop since after a few days or less it will be out of battery life and will be 100% useless.
And also there is no point in taking a Playboy playmate either... She wouldn't last a day there and the rest of the time you'd be stuck by yourself. I think the idea was to pick somebody that you actually know who you could realistically take with you...
Honestly now that I think about it something that would be really good to take would be a really big sturdy knife. Something solid that you could use to hunt as well as defend yourself with. "Lock" style (for all you Lost fans).