Diablo 1 is really still fun. You can obviously tell that it was developed before the year of 2000 and while playing with 2 other friends, it is mostly fun, with a great atmosphere. The Gameplay really is outdated, you can ported back a lot when getting hit by enemies, balance is quite random. You need 3 people with full health potions each and still lose to the Butcher. Each player gets one level up, you try again and kill him within 20 seconds. Hellfire is "cool" but it is quite buggy. First you need to do some additional configuration (or install a mod), to be able to play with your friends over Hamachi or sth. similar. Also there are many bugs where items cannot be picked up, sometimes can only be picked up by the host, and many more. If you can look past these issues, it was also fun to play through this unofficial Add-on, at least once :-)
If you like deep interesting stories and characters and also enjoy Singleplayer 1st person shooters, this is a must-play for you! Also I would HIGHLY encourage you to play Bioshock 1 and 2 before this game and play the DLCs 'BioShock Infinite: Burial at Sea - Episode 1 and 2' (these are included in this Complete package) AFTER you finished this one. Your mind will be probably blown away, when you find out how all the 3 games and their characters are connected with each other ;-)
Never played WC1 or WC2 in my life before, but I always wanted to try them out. So what I have to say: WC1 is really not playable for me, because of the mechanics! I played RTS games like The Settlers; C&C Red Alert 1+2, Knights and Merchants, etc. but WC1 is in another league: You cannot send units to a place with your right mouse button! You cannot simply select more than one unit at once with your mouse alone! Basic things like that make it very frustrating and I stopped playing it after the first 4 missions. WC2 on the other hand is a great RTS imo. The gameplay is obviously also "dated" but it improved in so many ways, that I was really enjoying playing it today!