The following list has a definite me bias...I don't like playing DOS games on the PSP that I remember playing with my MS Sidewinder or the keyboard...On the PSP, the controls just become a bit awkward for me...(ie. Doom, Descent, Duke Nukem 3D, X-Wing, Mechwarrior 2, etc)...I also find RTS games are difficult without keyboard shortcuts and my beloved mouse...
Also, I tried to avoid titles that were released on multiple platforms (some platforms which are already emulated quite well on the PSP) and the LucasArts adventures since the SCUMM emulator does quite well...
My Top 5 suggestions...
1) Fallout
2) Master of Magic
3) Master of Orion (or the 2nd as has already been mentioned)
4) X-Com
5) Warlords 2 Deluxe
By category:
Arcade
Raptor (a lot like Tyrian)
Terminal Velocity (like Descent but simpler controls and gameplay)
Abuse (platform shooter [best there ever was for DOS]...controls could be a bit difficult on the PSP)
Crusader: No Remorse or No Regret (isometric shooter...was fun in the 90's...very dated now)
Dark Legions (from SSI...good quality game...sorta like Archon)
Adventure
Space Quest 6: The Spinal Frontier (Sierra was the only company that could really compete with LucasArts)
King's Quest 7: The Princeless Bride
Star Trek: Judgement Rites
Star Trek 25th Anniversary
Bioforge (Origin...short but tightly scripted sci-fi adventure)
I Have No Mouth and I Must Scream (if you can find it)
Relentess: Twinsen's Adventure or Twinsen's Odyssey (European Mario-style adventure with depth for DOS)
Star Control 2 and 3 (not sure if they're adventure but like Master of Orion with a plot)
Strategy (mostly turn-based and some city management type games)
Battle Isle 2 (sci-fi turn based)
Settlers 2 (medieval, cutesy city management)
Caesar 2 (Roman city management)
Lords of the Realm 2 (medieval, not cutesy city management)
Heroes of Might and Magic (yes...yes...yes...was a tough call between this and Warlords 2...HoMM 2 would be even better but I think it's Win95 only)
Dungeon Keeper (real time but not as time critical as Command & Conquer or Warcraft...no worries on the rush tactics)
Sid Meier's Civilization (started it all...just doesn't seem as good after playing Civ 2 and Civ 3...haven't played Civ 4 yet)
Sid Meier's Colonization
Sid Meier's Railroad Tycoon Deluxe
Jagged Alliance (turn based isometric squad based combat...X-Com in South America with drug cartels and no aliens)
Wargames
Empire Deluxe (cheesy yet addicting)
Panzer General (almost made the Top 5...beer and pretzel strategic wargaming)
Steel Panthers (great, in-depth WW2 strategy game)
Harpoon 2 (another that almost made the Top 5...modern naval warfare at its finest)
RPG
(Note: Ultima VII was released for the PSP as part of EA Replay...it was based on the SNES version...the DOS version was better but I didn't list it)
Elder Scrolls: Arena and Daggerfall (before Oblivion there were the games that started it all)
World of Aden: Thunderscape (classic SSI RPG...NOT based on AD&D)
Realms of Arkania: Star Trail and Shadows over Riva (good RPG stuff from the makers of Wizardry)
Wizardry 6 and 7: Bane of Cosmic Forge and Crusaders of the Dark Savant (looooong RPGs with lots of story)
Skyrealms of Jorune: Alien Logic (another original SSI RPG...almost an adventure game)
And the list of SSI AD&D games for DOS
Dark Sun: Shattered Lands
Dark Sun: Wake of the Ravager
Al-Qadim
Ravenloft: Strahd's Possession
Menzoberranzan
Some great gaming in the early 90's on the PC...that list leaves off the FPS, flight sims, and RTS games which were so great on the PCs and now tend to dominate the entire gaming market (except for flight sims...god rest their soul...too expensive to develop and a niche market...)
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