nami

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there are 8 mainline disgaea games, including disgaeas 1-7 and disgaea dimension 2 which is a sequel to the first game (released 10 years later). any of them are good to start with except for dd2 since it was an anniversary project and kinda suffers in quality. 6 was so bad that i skipped it entirely. 3 is largely inaccessible because they have not rereleased it yet (except on vita) so unless you have a ps3, it's better to just watch the story on youtube.

so really there's 5 games to pick from! all of the following are on steam:

• disgaea 1: originally on ps2, later on psp and ds with additional content, then ported to pc with everything, and then "remastered" as disgaea complete for ps4 and switch. the remaster sucks. disgaea pc is probably your best bet, sitting at $4 due to the winter sale going on right now. (edit: @YoshiKyon pointed out in the comments that there's performance issues with the steam release, so definitely let that factor into your purchasing decision...!)
• disgaea 2: also a ps2 game, later on psp with extra stuff. this one is also $4 on steam right now.
• disgaea 4: originally on ps3, later on vita with lots of extra stuff, now on switch, ps4 AND steam as disgaea 4 complete+. this one is currently $14! what a steal!! i'm partial to playing disgaea on consoles so i would recommend ps4/switch, but if you prefer pc it's definitely cheaper there.
• disgaea 5: this one was originally on ps4, then came out on switch and pc with all the extra stuff included. it's currently $10 on steam. again, i'd recommend the switch version but pc should be just fine too!
• disgaea 7: this is the latest release!!!!! it's on ps4, ps5, switch, and pc. pricewise it's about the same across the board since it came out in english last october. i played on ps4 when it came out in japan, then played the english version on switch. both were great.

ok now how to narrow it down

imo you should pick your starting place based on whatever characters/premise vibe with you the most. if you're sure you're gonna play all the games, i recommend going in release order since it's hard to return to older disgaeas where there's less quality of life features.

if you want to play any single disgaea just to see what it's like in there, i recommend 4. it is the best one. it's a great story, the gameplay/system holds up a lot better than disgaea 1, it's got hd sprites rather than 3d models (i dont like the 3d as much!) and it's affordable on lots of platforms!

if you like tactical RPGs already and somehow never played disgaea before, i think 5 has the best gameplay. it FEELS GREAT to play. 7 feels good too but it's still kind of recovering from how badly they fucked up in 6. the only downside of 5 is that the story is the weakest of the set. i still care about the characters but i think the others from this list are a lot better.

if you want to splurge on the most modern disgaea with a great story and cast, highly recommend 7. it is my next favorite after 4. i still think the 3d models are a little goofy but they're getting their footing with it... it was a lot better than i expected going in.... i love the cast, i love the writing. this is the only disgaea that doesn't have tenpei sato's music, but i still liked the songs! there's a few bangers in there. notably different vibe from the rest though, and i think the cutscenes suffer from losing the character acting in favor of just having vn style, but there's also more illustrations because of that and those are great. ok that's enough about 7, i really liked 7...

disgaea 1 is SUPER beloved by fans to this day, so i think it's still completely valid to start here. if you're used to playing older games you'll have a good time with it. if you don't enjoy tactical rpgs and grinding and whatever i think you will suffer. the story is great and iconic. laharl etna and flonne are extremely fun. there's a lot of people who think disgaea will never be this good again and i disagree with them but i also see where they're coming from. 1 rules.

i've said practically nothing about disgaea 2 but i REALLY LOVE THIS GAME!!! i don't know if i can recommend it as your first disgaea because the things i like about it are overshadowed by how much i love 4 instead. 2 has a really wonderful love story. to my memory there's some bits in the localization that i'm sure they would do differently today (namely taro's nickname lmao) and tink is a freak (/pos????) so i'm worried you'll get a weird impression if you start here but like... fuck, the story's great. i love adell, i love rozalin, i love disgaea 2.

this is the end, i've said too much

i hope this post can guide you. please play disgaea 4