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Take a Blast to the Past
Many gamers grew up on the classic games of the 1980s and 90s, and we miss the heady days of discovery that went along with gaming during that period. Some modern gamers are too young to remember, and thus have not earned their gamer's stripes by going "W" and being eaten by a verminous grue.
For all of those young and old that want to experience the heyday of classic gaming there is good news: many of the best and brightest classic games are now free to download and play due to their classification as "abandonware", which essentially means no one is distributing or selling the game anymore. Several great sites have surfaced over the years that have cataloged these games and made them available to the public, as well as a great selection of shareware and freeware games.
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A Word of Warning
Many of these games are very old, and will not work properly on modern computers without a little tweaking. Make sure to read the various guides on the sites for tips and tricks for making these games work.
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Nintendo8 is a great site for a quick game because it doesn't even require a download. All the games run in Flash, right in your browser. Almost all the classic Nintendo and even some Super Nintendo game are available. The only downside is that there is no real configurability, and the keyboard controls for many of the games are a little less than intuitive.
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Home of the Underdogs
Home of the Underdogs is the undisputed king of abandonware sites. It has a searchable directory that is also available to browse by genre, year, producer, license, and operating system. Many of the games also have the manuals and extra materials conveniently scanned into PDF format. Each game is described and reviewed, with screenshots where possible, and rated. The site also covers other underappreciated games (hence the name), so be aware not everything has a download available.
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XTC Abandonware is another site that has been around for a long time. Their catalog is not as complete as Home of the Underdogs, but it often has some of the more obscure titles that don't seem to count as underdogs. Their site's navigation is a bit odd, so be aware you may have to really dig in to find the gems.
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C-DOS Abandonware Games
C-DOS, as their name implies, has a focus on preserving the classic games from the DOS era, which was (for those of you too young to remember) the operating system used on PCs prior to Windows. While Microsoft had a proprietary version called MS-DOS, there were also open versions and alternative versions.
The selection of games is awesome, lacking not a single title I can think to look for. The problem is getting them to work. You need at least a couple of little tweaks, and often need extra programs, to get the DOS games to run correctly. There are instructions and guides on the site, but they can often be a little lacking for the non-technical among us.
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Abandonia is a newer site, and their design and navigation shows it. They have a great selection and everything is very easy to find, using tags and categories familiar to blog readers. This site, like Home of the Underdogs, reviews software that is not abandonware, so make sure that the neat game you get all excited about has "abandonware" as one of the tags, otherwise you will be very disappointed.
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Classic Trash, like Home of the Underdogs, have been around since the beginning of the abandonware scene, and their selection shows it. If you can't find it among the underdogs, Classic Trash should be the next place you search. This is another site that reviews games that are not abandonware or otherwise free, so don't get too excited when you see Baldur's Gate or other more modern games.
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The abandonware scene is a great source of classic games, but be aware that there is a limit to what you can play on a modern system. Windows XP has compatibility modes, available through the program properties, but they often don't work. Read the guides on these sites and do your best, but some of these games will simply not work on modern PCs.
Even with that limitation, it is wonderful to see that Zork still has its appeal and that Might and Magic 4 really was as revolutionary as I thought when I was 13. These games are what made a lot of us into gamers, and their replay value will never die.
Have fun and keep gaming!