Well, first off, without knowing what types of games you like, it would be hard to give good recommendations. That being said, here's what I'd recommend out of my collection (which is actually pretty small, I'm realizing).
Note that all I play are RPGs, so that's what these all are. They're not ranked in any sort of order, just the way I want to present them.
Also, since the PSP is a "dead" system, and not even Gamestop is taking games for them anymore, all PSP games are out-of-print.
1) Valkyrie Profile: Lenneth - A port of the PS1 game, it's a very good game. It is slightly a step back from the NA PS1 game (both the JP and NA PSP games are based on the JP PS1 game, there were slight changes made to the NA PS1 game), but still strong overall.
It's turn-based, but not in your traditional sense. All of your characters can attack at once, in any order or timing (until they run out of attack points), and it lets you make combos that work better or worse on certain enemies.
Plus, with 3 endings and a bonus dungeon, and a large cast of characters that, while you do have to give up, you choose who to give up, that's at least 2 playthroughs worth of game play (the 3rd ending is a bad ending you can take anywhere and continue from).
2-5) Persona Franchise - There are actually 4 Persona games available on the PSP: Persona 1, a new translation/port of the PS1 game, Persona 2: Innocent Sin, a port of the PS1 game, never before released in NA, Persona 2: Eternal Punishment, a PSN release of the original PS1 game, sadly, it has the original translation, and doesn't match Innocent Sin, and Persona 3 Portable, a remake of the PS2 game (FES, not vanilla, although it's missing The Answer).
Persona 1, 2:IS, and 2:EP are all dungeon-crawling, turn-based games, where you make deals with demons and use their cards to create Persona. They're also much closer to the rest of the Shin Megami Tensei franchise (point of interest: Persona 1 is actually a spin-off of Shin Megami Tensei ...if, which was a side-story to the mainline SMT series).
Persona 3 Portable lets you pick your gender, and is a combination of social game, dating sim, and dungeon crawler, although you do lose some of the freedom of movement from the PS2 game (in the world, you select where you want to go, rather than it being an open world). Even if you've played the original (vanilla or FES), the female protagonist's storyline is worth a play through, as she's not just a gender flip of the male protagonist.
6) Kingdom Hearts: Birth by Sleep - Yes, it's a Kingdom Hearts game. However, as a prequel, BbS is a stand-alone game. Knowing the story of the first two games will definitely enhance your experience, and the game does end on a downer note, to lead into KHDDD and KH3, but it's a really good game, and one of my favorites in the series. Especially with the way you can combine your abilities to create new ones. And Command Board. Which is a game in and of itself. It's Fortune Street light, if you have a Wii. Or similar to Monopoly, if you don't.
All that being said, however, if you have a PS3, I'd actually recommend not getting BbS for the PSP. Instead, get Kingdom Hearts 1.5 and 2.5 for the PS3. 1.5 has Kingdom Hearts: Final Mix (originally on PS2, FM never available in the US previously), RE: Chain of Memories (originally a PS2 remake of a GBA game), and a movie version of 358/2 Days (originally on DS, good gameplay, but tedious to get through). 2.5 (out in December) has Kingdom Hearts 2: Final Mix (same as KH1:FM), Birth by Sleep: Final Mix (which adds an entire new "world", in addition to other things, also never in the US), and a movie version of RE:coded (DS remake of a mobile game).
IIRC, they're $30 each, still available, and well worth it.
7) Tales of Eternia - My last recommendation, and a bit of "Tales of Eternia? What's that?" to anyone who only knows the English releases of Tales games. To anyone who knows a bit more, it's more of "Eternia? But that was a PS1 game..." And yes, it is a PS1 game, released in the US as "Tales of Destiny." However, it received a PSP port, which never made it to the US.
Now, of course, the question turns to "But Dessa, I didn't say I could play Japanese games..." Fret not! The PSP game wasn't released in NA, but it was released in EU, in English! Looks like there's a non-glitch version* on "Buy it Now" on e-bay for $39.99 with free shipping, even.
Eternia was the 3rd game in the Tales series, and is a 2D action RPG. It's not a particularly hard game, but I find it very enjoyable, and it's probably my second favorite game in the franchise (behind Abyss).
*There is a glitch, where the game will freeze after one particular boss. Always make sure that the game you buy is either listed as "non-glitch", or that the seller doesn't know what you're talking about (since they would know if it hit them while playing).
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