Firefly. Watching Serenity, it's pretty obvious they're trying to hit several seasons' worth of story beats in as little time as possible. Seeing it as intended would have been really cool.

Honorable mentions (in no particular order):

Fight Club

The Iron Giant

Grindhouse

Waterworld

Dredd. Karl Urban always gets me in the door, but the movie ended up being pretty great.

Treasure Planet.

It's probably a good thing that Disney's forgotten about it. I don't wanna see them try to remake it.

That Speed Racer movie that the Wachowski’s made. I think it’s a fun film and I feel fortunate to have found a handful of Lemmy users who also appreciate it.

Mystery Men. Probably 20 years ahead of its time. I don't think people had been inundated with superhero movies enough to appreciate the deconstruction. Aside from one or two short pointless scenes (what purpose did the skunk scene serve?) the film is incredibly tight, peak comedy.

Event Horizon. I consider it in-universe canon for Warhammer 40,000.

Weird Al's film UHF.

In a just universe it'd have made a ton of money, spawned sequels, and set Al up as just as successful a screen performer as he is a musical performer. As is it flopped in theaters, but gained a well-justified cult following on home video afterward.

Dirk Gently (the last TV show)

Better off Ted

Dead like me

I don't know that Water World ever got a later following, but I love it and it's still an original take on the post-apocalypse genre.

No one else gonna mention the 90s Mario Bros movie? It was one hell of a commercial flop, and set back video game movies a long time, but i love it.

Blade Runner 2049 was technically a commercial failure by hollywood standards.

Scott Pilgrim and Speed Racer were commercial failures. They are in my humble opinion two of the best cinema that get out of Hollywood. Being the commercial failures that they were Producers abandoned this side of the craft for the slop fest that we’re in now

There’s some beautiful TV series that were cancelled after one season : Firefly (Whedon is an awful being), Almost Human, Kaos, Altered Carbon (they should have cancelled it after one season, the second not only killed the franchise it killed the possibility of doing more) to name a few

Jesus. Probably most of my media library? It's genuinely a surprise when anything I really like is successful.

First thing that comes to mind is Blade Runner 2049. Film flopped hard, but it's a god damn masterpiece. Absolutely perfect way to build on the ideas presented in the original, while also playing with a whole new set of notions on top of that. Gosling continues to be incredible, the soundtrack is pure magic, and Denis Villeneuve is one of the best filmmakers in the world.

Donnie Darko. It perfectly fits your second criterion. It was an abysmal flop in theaters, mostly because its ads got pulled because it featured

It had a budget of $4.5 million and only made $500k in theaters. But it later exploded on DVD and made $10 million.

Dark Matter.

I was primed onto that show after playing a lot of Fractured Space, which was also a commercial failure.

Reaper and Santa Clarita Diet.

No idea if they were flops, or if they just got canceled because the actors were up to other stuff, or writers died, or the network heads were coked up or whatever idk. They were canceled before they could finish and im sad.

One of them is Rock & Rule. I encourage everyone who's into cult films/animation to see it for themselves if possible, and try to seek out the Canadian version even though it's rare.

Short summary: This movie almost bankrupted Nelvana animation studios, who spent $8 million on it for it to make about $33k in 1983. The colossal flop was mostly due to the distributor MGM/UA not knowing how to market an adult-oriented animated feature and recasting/redubbing/editing the fuck out of the US release version.

To compound on the matter, the original print of the Canadian version was lost in either a fire or a flood, sources are mixed on what happened, and the remaining version is long out of print. A lone VHS copy of the Canadian version was digitized and released on DVD by Unearthed Films in 2005.

Due to the films still being officially out of print (and one version destroyed), physical copies are rare and expensive (physical Blu Ray was going for $400+ on eBay last I checked). And you're likely only going to find the heavily edited US version unless you specifically search for the 2 disc DVD set. The Canadian unedited version is non-existent online, and neither version is available to stream. The US version is on YouTube though.

Overall - great movie, great music, fantastic animation. Very 80s. It's a 10/10 to me.

firefly is the most obvious. I remember sticking around for john doe and after they canceled it I stopped watching anything that night and then john doe got canceled because its ratings dropped like a crater.

I guess it technical made money but Kung Pow! Enter the Fist.

I saw it in theater and remember everyone laughing through the whole thing. Absolutely absurd re-dubbing of a couple of old kung fu movies by the guy that later wrote and directed Ace Ventura and wrote the Jimmy Neutron movie. The reviews were utterly horrible (deservedly) but undeniably funny. I still quote it all the time.

For the unaware that where the "That's a lot of nuts!" comes from.

Pantheon, the TV series.

One of the best shows ever, IMO, so good I can’t say much without spoiling the premise in a Outer Wilds kind of way.

Yet it was trampled by AMC and their failed streaming service. What a mess. I’m not sure it’s possible to even watch legally?

The Rocky Horror Picture Show was a flop on release but still has special runs in theatres now some 50 years later.

Soldier(1998) with Kurt Russell

I dunno whether it's my favorite, but I'd have liked more Firefly episodes.

Oh I have a few!

Office Space

The Life Aquatic with Steve Zissou

The Beach

These three are probably my top favorite films of all time. I also have a soft spot for Tron Legacy

Surprised no one's brought up The Room (2003) yet.

Really hoping that the Bob Odenkirk remake becomes a real thing.

Freddy got Fingered

Tremors?

Most recently, Super girl was underrated.

I also liked The Dead Don't Die.

of the only two Transformers DVDs Blockbuster had growing up, one of them was THE TRANSFORMERS: THE MOVIE. i always figured that it was the main Transformers thing, because, y'know, it's The Movie! no idea that it wildly underperformed, drew the ire of parents everywhere, and was torn to shreds by critics (who compared it unfavorably to the movie where the GoBots fight literal rocks)

granted it was vindicated by the recent theatrical rerun. i got to see the movie in a packed theater, and it finally broke even 40 years later

Obligatory Ishtar