trying to think of shit off the top of my head. king of fighters 2000 saw snk go bankrupt during its development. they were able to keep living thanks in part to other companies stepping in due to kof's overseas popularity, but it was still widely considered the end of an era. story goes that they had to move out of their hq next to esaka train station (which was featured in one of the most popular stages in the series), and that led to this song https://www.youtube.com/watch?v=1M_W8bGZt94

the next couple KOFs after 2000 actually had a different publisher and the development went to a different studio that had been founded by the SNK founder I believe who had left sometime before

L.A. Noire might fit that ticket.

100% Panzer Dragoon Saga--developed with enormous ambition as a Final Fantasy 7 challenger by a much smaller team with way less jrpg experience on a much less successful console--ended up the legendary peak and death knell of the Saturn (and Team Andromeda) in a lot of ways. Pathologic 2 maybe? Okami for Clover, 13 Sentinels for Vanillaware (def remains to be seen but kinda feels this way).

Sonic Adventure 2 fits the bill for being the grand finale to Sega's history as a console manufacturer

I know Ion Storm is already present on this list in the form of Deus Ex, but I'd vouch for Anachronox. A roving balls-out planet-hopping epic. Tom Hall, John Romero and other senior staff would leave the team soon after its release.

i should've thought of panzer dragoon saga! not sure they approached it as a last-ditch effort or whatever, but it was certainly a swansong.

anachronox is another great pick.

not sure about la noire or sonic adventure 2, but i'm open to further convincing! haha

The Great Ace Attorney 2: Resolve
series has been pretty dormant outside of ports so I would say it failed(not taking away any of the quality from the game).

Last Window: The Secret of Cape West
another VN but they went bankrupt on their last game. Cing's sequel to Hotel Dusk and seems to lean on the side of good.

Too Human

Intelligent Systems was explicitly told that Fire Emblem Awakening would be the last Fire Emblem game if it didn't sell well and it ended up saving the franchise

Thunder force v. Most expensive title made by technosoft but didn't meet sales expectations, they stopped making shmups and the company went under a few years later. VI was made after Sega bought them out.

as an alternative to sonic adventure 2 I'd say shenmue... meant to be a revolutionary new type of game and a killer app for the Dreamcast, and it ended up bringing sega to the brink of bankruptcy and pulling them out of the hardware market. not the only factor that killed the DC but sort of emblematic of its failure

Was also thinking Shenmue

I think Thief II and Vampire the Masquerade Bloodlines both fit the 'swansong' and 'masterpiece' categories pretty well. Thief II sold well for Looking Glass' standards, but they didn't get the royalties from it in time to prevent them from going bankrupt after pretty much everything they made in the late 90s (apart from the original Thief) underperformed sales-wise. VTMB sold less than 80,000 copies on release and the financial hit that Troika took from it is probably part of why Bethesda were able to outbid them for the rights to Fallout 3. And most people that've played either game will tell you they're near the top of their respective genres (for good reason).

oh yeah there's also batsugun for being toaplan's last game before bankruptcy and oft called their best

idk anything about too human. how's it apply?

wrt games that ended up being the final game before a company went bankrupt... i mean, were they ALL-IN EFFORTS, or were they just a weak last gasp? i need more info for some of these. :)

thanks!

iirc DoDonPachi DaiOuJou was supposed to be the last arcade game by Cave and it ended up bringing a new age for the company

DoDonPachi SaiDaiOuJou as well, though that one was indeed the end

for the record, Final Fantasy IIRC isn't really a last ditch effort for the company, but rather the main designer. Up to you if that disqualifies it or not doe

in uematsu's own words, the company was actually on the verge of bankruptcy.

https://www.wired.com/2009/07/final-fantasy/

I'd say Journey fits the description here, Jenova Chen mentioned that during the final months of development, thatgamecompany was more or less in bankruptcy and that some of the developers had gone unpaid at the time.

How about Grim Fandango? Swansong for a storied team and essentially an entire genre (for a while at least)

Darksiders 2 was so expensive and ambitious but underperformed so hard it was one of the main reasons for THQ to go bankrupt within a year.