Only to a collector who will pay for them. I know that sounds like an obvious answer but that's the way it is. I'm sure some issue are worth more than others from that period based on content. For example, I have a '66 issue where the Beatles are interviewed. But I won't sell it.
Ebay would be the place you would get any kind of money for them.
If you sell in bulk to a dealer, you'll get maybe 1/4 to 1/3 of their value, if that. Your best bet, unless there is a good way for you to sell them locally, is Ebay. Selling issues individually gets the most money but it's a huge hassle. Your best compromise would be by years - people like that.
Be aware that some single issues are worth a lot more than others (I don't know which these are, other than the very first issue). Watch Ebay for a while to get a feel for value.
Matt, actually, yes, I might like to buy it off of you if the issue is in your possession. Personal memories ... (I think it would have been the August or September issues.)
I've actually read in Playboy, (yes some of us actually read it, at least after reviewing the pictures. )that many back issues have a lot less value then you think you could get when sold. The reason is so many people have saved them over the years so rarity is not much of a factor. It's just one of those mags that people don't like to throw out.
That's not to say they don't have value. As someone already posted some issues will be more valuable then others because of the individuals featured in the issue and selling them individually will definitely bring in more money.
On a side note I do have the original Jenny McCarthy issue autographed. I wonder how much it’s worth? Probably not much but I’ll have to go to Ebay and research the value.
As with anything like this, the question becomes whether you want to get rid of them to make space, or to make money. If you're just looking to clear out some space in the basement by getting rid of a bunch of magazines, I'd put them up on ebay in cheap lots (by year is probably a good idea), or list in more places like the HTF, and hope that a collector got ahold of them. You won't make much money this way, but you'll probably help someone fill in a hole in their collection. If you just want to make a few bucks though, you're probably better off just checking ebay for single issue prices (try searching completed listings for a price guage). I know from comics that large runs aren't typically worth much, and it's the odd singles or short runs that are sometimes worth money.
If the issues are in very good condition, they're worth a fortune, especially ones that old. Just look at Playboy's catalog for how much they charge for back issues.
Selling on ebay is not that much of a pain, especially if you are getting good money. How hard is it to package a magazine & mail it? It's not like you're trying to get rid of your 50-piece home gym set.
Drop the magazine in a flat-rate priority envelope and charge $4.25 shipping. That's $0.40 over the actual rate. You can even pay for priority postage on the USPS website, print it out, tape it on and give it to any postal delivery worker, saving the hassle of going to the post office.
If someone buys more than one, charge an extra dollar and you should still be able to get 2 issues in the same envelope.
If you sell them in lots, then it'll start getting to be a hassle because you'll need boxes, and if you don't have a scale, you'll have to go to the post office for proper postage. Of course, those new self-serve kiosks are pretty nice.
And, as others have said, watch ebays prices before you start so you can set a proper starting price.
Let's take it to the extreme and say that someone has every single issue ever printed. (Between my own collection starting in the early 80's and a friend's dad's going back to the beginning, we're pretty close -- missing maybe 10 total.) How much do you think a complete set would be worth? More than selling individually?
I actually like going through periodically and reading the jokes, and also seeing the stereo ads of the various eras.