We obviously started on Wolfenstein, then Doom.  But obviously when Quake showed up it was leaps and bounds ahead of the other two.  We used to play against each other using a computer to computer ribbon cables even before ethernet existed.  But the reason why it was fun was because more than 1 person could play at once. 

That said, the free roaming action, the storyline, the embedded humor, the action sequences, and the problem solving of The Secret of Monkey Island beats just about any game I've ever played, except for the Legend of Zelda series.  I would give anything to be young enough that I'd have the free time to actually play it again.

>the problem solving of The Secret of Monkey Island beats just about any game I've ever played, except for the Legend of Zelda series.  I would give anything to be young enough that I'd have the free time to actually play it again.

I don't know if you know, but there was a remastered version of the first two Monkey  Island games released.  They redid the graphics, and added voice actors.  I bought them on a steam sale for cheap, and we played them as a family on our living room TV.

You can also hit pg-up/down to toggle between the old graphics and the new graphics engine, which was fun for showing my daughter the 90s equivalent of having to walk to school uphill both ways in the snow.

Having played it through the second time, did the game hold up?  Or is my memory of the game being fantastic skewed because I was only able to compare it to games of that time, and when compared to games of modern day does it now feel lackluster?

Because if you say it was even moderately enjoyable, then just like how I only bought the Nintendo Game Cube so I could play the original Animal Crossing, it looks like I'll be signing up for Steam just to relive my childhood.

I would say it does hold up. Probably the old graphics would make it hard to enjoy, but the remastered versions bring the game into the modern(ish) era.   I especially liked playing it with my daughter because I got to see her experience it for the first time, so if you have a friend or loved one that has never played before, it's fun to play together.  I remembered a few puzzles, but was surprised by how much of it I did not remember.

Steam sales happen on a fairly regular basis.  The next one will probably be around Halloween, so if possible you can purchase it then.  I think you could create an account now, and it add it to your wishlist or something and steam will email you when it goes on sale.  I actually don't use steam much, so maybe someone else can give better advice. 

This site is predicting a sale at the end of October:
https://www.whenisthenextsteamsale.com/

Or - it's only $10, right now so why wait if you have the time/money to play now. You can also get the first 4 games for around $25.

Also looks like Good Old Games has the same prices, so if for some reason you prefer them to steam:

https://www.gog.com/game/the_secret_of_monkey_island_special_edition

I think games from GOG are DRM free, while most steam games are not, so I guess that's a reason to purchase from GOG instead.

GOG gives you the whole gamefile to do so as you wish.. I feel they are a bit better at updating the game for modern systems.

I used to play this a lot on my 8 MHz DOS 3.2 IBM PC clone

You can apparently play this online emulator, but it seems a bit buggy:

https://archive.org/details/IsleWars

I still play Civilization 3 to this day.   I hate to admit how many hours I've spent, but it's a perfect game when I need to focus an overly busy mind.  I've played all later versions in the Civilization series, but 3 seems to best maintain the balance between being challenging and entertaining.   The original Civ3 stopped working as Windows evolved, but Steam offers a version that works just fine.

I also really enjoyed the Myst/Riven series.   There is an updated version named RealMyst which is available now for mobile platforms which improves the graphics giving them a more 3D feel.  And Steam also offers all of them although I've not tried them via Steam.  If one enjoys the graphic adventure type games, they are worth checking out as I think they still hold up and are historical in that they greatly influenced the development of the genre.