I could get behind this. He's got awful money management skills in general ("Balloons ain't cheap!"). Couple that with bad luck and you got your answer as to why Wario always keeps losing whatever he gains.
To be honest, he even gambles in the games to some extent. In Wario Land, you can double your coins in a gambling minigame. The exact same game also appears in a larger format in Wario Land for the Virtual boy.
 
I like to think Ashley picked up her apparent newfound love for music and guitar-playing in Crazy Ga;axy from Mona. Makes sense, right?
 
I'll post a few of my headcanons about Wario's life.

- Wario was born a Star Child. However, for some reason, his parents were unable to receive him and so Wario was promptly sent to the Brooklyn region of the Metro Kingdom to be looked after by other humans, which is how he eventually came to meet Mario. His parents moved to Diamond City shortly after he and Mario had a falling out

- Wario's adoptive parents were a good for nothing deadbeat involved in construction (Foreman Spike) and his hardworking housewife. His mom was related to Mario's family and that's why they are cousins. Spike eventually left them and he and his mom had to take up farming to support themselves. Much of Wario's strength comes from toiling away in the fields to support himself and his ma.

- Despite moving to Diamond City and making a lot of new friends, Wario never quite forgot his grudge with Mario, and when news of Mario's heroics across the world reached him, he was furious and made quite a few attempts to attack Mario, all of them unsuccessful. Wario's plan to take over Mario Land didn't come to fruition until Orbulon crashed in his house and introduced Wario to his friend Tatanga.

- Games like Wario Blast and Wario's Woods take place after Super Mario Land 2 but before the Wario Land series, as they consist of Wario still trying to get back at Mario but indirectly. Virtual Boy Wario Land happened while Wario was making his way home from the events of Wario Land 1, and it was also in this game that Wario discovered his immortality. The events of both games went a long way to boosting Wario's self-confidence, which is why he stopped attacking Mario (at least for a while) and took up party invitations, all while juggling his life as an adventurer.

-The events of Wario Land 3 and World also happened within a very short gap, and both experiences shook up Wario quite a bit, as he lost his castle, and encountering guys like Rudy and the Black Jewel was quite shocking for a guy so assured of his own immortality. He became somewhat homeless for a while and it was during this time that he encountered Waluigi, another fellow mischief maker who, for his own reasons, was angry at the Mario Bros, and he became Waluigi's partner and training coach.

-Shake It takes place before Wario Land 4 and those two games together tell the story of how Wario got his fighting spirit back and then, after trekking through hell and meeting Shokora, not only gained a lot of treasure, but also walked out of that Golden Pyramid a slightly changed man. Afterwards, he returned to Diamond City, a stronger, better, and smellier man that he was when he left. However, he has no idea what to do with himself.

-Master of Disguise is what gives Wario the idea to enter videogames as a market, which culminates in him calling all his old friends, and new ones, to open up WarioWare. And the rest is history.
 
Here's some others one but this time about Wario and Waluigi's relationship.
  • Wario and Waluigi only met each other when they were both adults and already quite acquainted with a life of crime. They are partners above everything else. This doesn't mean they aren't friends, or that they don't enjoy each other's company, but that most of their interactions are based on a common goal and they are busy with their separate lives at the end.
  • Wario has taken Waluigi on a few treasure hunts but they mostly turned out badly because they couldn't stop bickering or trying to steal stuff from each other.
  • Wario is Waluigi's training coach and he's the one who helped Waluigi become a better sportsman for his tennis debut. He's done a lot for Waluigi's self confidence but at the same time he's also taught him some really bad habits.
  • Wario is pretty much the only person Waluigi has any measure of respect for.
  • Wario has no idea what Waluigi's life used to be like or why he hates Luigi so goddamn much, and he never really cared to ask. Waluigi is pretty secretive and stingy about that stuff.
  • On that token, Wario keeps Waluigi in the dark about his relationship with the Mario Bros, mostly because he's embarassed he used to hang out with them.
  • Wario intentionally never introduced Waluigi to his Diamond City friends because he dreads the possibility of Waluigi either picking fights with them and getting them mad at Wario, or worse, him getting chatty and relaying all sorts of embarassing Wario stories to them.
  • However, he has invited Waluigi to do freelance work at WarioWare. Waluigi refuses because he knows firsthand Wario has no intention of paying anyone, and because he is too busy training and scheming.
  • Wario constantly tries to get Waluigi to eat more and pack more weight.
  • Waluigi constantly tries to improve Wario's hygiene and personal grooming.
  • Wario and Waluigi have tried living together for a while, but for dozens of reasons, ranging from petty non-issues to extremely destructive disagreements, they both agreed it was better off to live separate.
  • All 4 of the Bros speak Italian to an extent despite Wario and Waluigi not quite being Italian. Wario is fluent but he's more comfortable with English or German (as he is part German). Waluigi is of Greek descent and he never bothered to learn Italian until he started hanging out with Wario and he was pissed that he and the Bros could have conversations in a tongue he didn't speak, so he aggressively learned it out of spite and he is still pretty rusty in most aspects.
 
Here are some of my Headcanons.
* Wario bought a DVD box of the series Silverzephyr so he can go in whenever he wants.

*Count Cannoli has a Cat names Parmesano.
He replaced Goodstyle with it to have some company.
It appeared at the end saving Carpaccio.

*Terrormisu likes to clean in maid outfits and wathing carnevals.

* Goodstyle turned back into a staff because he is afraid of the afterlife.

* Carpaccios mansion is in Venice.
 
Wario secretly loves vegetables, but he doesn't eat them because he thinks it's bad for his image.

Also, Wario is nearsighted and needs glasses to read, but he never got any because he doesn't like to read anyway. (I think he would look awesome in glasses, tbh.)
 
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I also like to think that since Wario has such poor eating habits, he tends to have really weird dreams. Some of them so weird, it even freaks HIM out. He shudders at the thought of those and never dares to tell them to anyone. But even so, in spite of all that, he STILL chooses not to eat healthy. Maybe he gets some weird microgame ideas from his dreams, and that's why there are some strange microgames. Or maybe, since he's relatively close to Mona, he was willing to open up to her about his strange dreams, hence the reason why Mona has the strange microgames.
 
Some other headcanons regarding Wario & Waluigi
  • Wario's mom is very proud and supportive of his son and his friend's criminal lifestyle, as she passed much of her greedy yet hardworking and driven mindset to Wario who in turn taught a good portion of it to Waluigi. She likes to dote over the two of them and Wario feels a little embarassed by it, but Waluigi loves to visit her because she is the closest thing he has to a family.
  • Waluigi met Foreman Spike at the age of 17 when he was going through a rough time and struggling to make ends meet. Possibly because of a slight resemblance to his estranged son or just being impressed with the young lad's skill for machinery and hardworking ethic, Spike hired Waluigi to work for him in his Wrecking Crew. This is around the time Waluigi would meet Mario for the first time and, a year later, his hatred for Luigi would truly initiate.
  • Wario & Waluigi never really talked about their relationship with Foreman Spike and neither of them really cares to.
  • Waluigi has a pretty hard time explaining to some of Wario's more normal family members how can someone be an evil tennis doppelganger for a living.
  • Wario's Warehouse is a dramatized version of events that did take place during the time Wario & Waluigi lived together, before Wario moved to Diamond City full time. They are heavily biased on Wario's perspective and that's the main reason why Waluigi is written as such an idiot in them.
  • Every now and then one of the two will crash for a period of time at the other one's house, usually Waluigi more often because Wario leaves his door open to any friend and because Waluigi's home is often in disrepair from the constant training routines and haywire inventions. This is good for Wario since Waluigi agrees to do most of the housekeeping and cleaning, and since Waluigi never has a lot of money, he earns his keep in a way.
  • One of the reasons why Wario & Waluigi mostly live separate is because Wario's pets, which are usually just his chickens and whatever stray animal (mostly cats) wanders into his house, and Waluigi's pets, Piranha Plants and whatever other freaky monster or inanimate object he's adopted that week, just cannot live together.
  • Mona actually gets along very well with several of Waluigi's more monstrous critters whenever she drops by.
  • Waluigi is prohibited from using Wario's showers because of his intensely loud and horrifying singing in the bath.
  • Every now and then one of Wario's old acquaintances from his more evil days drops by for whatever reason. The first time Seizer dropped by the house, Waluigi was terrified the Grim Reaper had actually come for his soul until Wario just explained that it was an old pal who had come by to pick up some mail. The two of them play videogames with Fauster once every month and Ashley gets very jealous when she discovers they just hang out so casually with such a high ranking lord of the demon realm.
  • Wario has a little bit of plumbing experience mostly picked from the days when he and Mario used to hang out, and he's the one who tries to take care of whatever plumbing issues the house has. Waluigi is an abysmal plumber who somehow ends up destroying the sewerage system of the entire quarter if tasked to fix a single leaky pipe. Both of them utterly refuse to call the Mario Brothers for help.
 
Does Wario have take off his overalls when going to the bathroom?
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He doesn't
 
I always envisioned Wario as starting out as a dweeby loser who didn't really have much of anything to do with Mario, very insecure and kind of lacking in stamina (note how slowly he gets around in Wario Land 1; that's him pacing himself-- energy conservation).

Personally, I like to think that Wario is just some street rat that grew up picking pockets an' stuff (and that's where the greed and gluttony come from, in addition to Wario already liking the stuff-- a heart once starved, and all that). He didn't have anything at all going for him, really, no purpose in life, a real nobody with no interests other than food and money because he was an urchin. (Note: I personally discount his appearance in Yoshi's Island DS as being canon, because it's just a remake of an established title and only included the extra children as gimmicks. In other words, SMW2: Yoshi's Island is canon, Yoshi DS is not. So when I say that we don't know anything of Wario's past, I mean it's completely shrouded in mystery. As far as I'm concerned, Wario is a name that he took for himself, to distinguish that he was kinda Mario but at the same time "fuck that guy, I'm-a WAARIO." Because really, let's be honest, that's the kind of name you come up with for yourself, not one that you'd force on your children, because at least it's you that suffers from any teasing and not someone else. I wouldn't in a million years name my kid "Tahu" or "Pokey" but for me it'd be an absolute joy to throw the name around and be referred to by, and it's probably the same deal for Wario.)

This is about as far as I can explain without going to an even more considerable amount of detail: it'd take a while to be able to truly articulate my position, and as you can see, this disjointed ramble is the best I can do with whatever amount of time, but I'll try to summarize.

Little Orphan Street Waat sees a whole bunch of Mario stuff everywhere around the time of Mario Bros. 2 or smth, is like "hey I kinda resemble this guy," and decides to copy his every move so maybe he can end up in the same place; insecure cuteass humble beginnings Wario finds himself, starts to develop as a person through the interactions he'd never had the chance to have before then, due to always needing to hide away-- love of food and money comes from being a penniless starving child nobody, everybody who knew him was kind of nyehhh towards due to his larger size, and perceived 'unhinged dullard' status as a result of his cock-eye and habitual fixed grin.
Since nobody gave a shit about him, he kind of had to teach himself damn-near everything, and since he'd always been seen as an idiot, in true WAArio fighting spirit, became this scholarly-ass man that we see in his earliest appearances. Of course, since knowledge and cunning was all that he had, he was kind of boring and a nuisance to everybody that interacted with him, which only made him irritated and disheartened, and all the more determined to be a part of their lives. That is, until the events of Wario Land occur-- suddenly, a whole new world opened up to Wario, and all of a sudden, he was starting to do his own things. Instead of competing with Mario to try to buy Peach some Samus doll, he fucked off to some forest and conquered the whole damn territory... granted, not hard to do when there's only like three people in it.
From there, he continued to experiment in different venues (see Wario Blast and the aforementioned Wario's Woods) before getting his shit stolen from Captain Syrup, and the ensuing adventure caused him to 1) settle on his passion: treasure hunting and exploration and 2) (eventually) develop a taste for short-sleeved shirts. At some point after the adventure, he decided to do something about his shitty stamina, and thus took up weight lifting, and because he's-a gotta show off those sick pythons, he started wearing t-shirts more often than the usual yellow cardigan. His intellect would disappear from his speech (a compensatory tactic to offset his goofy appearance, no doubt), instead being funneled into learning how to program.
He eventually sees some incredibly gaunt man at some point while strolling through town-- the guy tries to pick his pocket, but Wario picks his instead, proceeding to taunt him. Then, halfway recalling his own shitty start, he gets an idea, and offers Waluigi the chance to help-a him out, cause there's this doubles tennis tournament and I want'a get the boatload of cash that comes with the trophy.
Later on, after spending all the stuff from whichever Wario Land on various things, he gets the idea to open up WarioWare as a means of getting fast cash. One thing that's of note is Wario's lack of castle-- this just further symbolizes Wario's change of mindset, how he no longer gives a fuck about whatever the hell Mario's doing, and now cares more about experience over possessions (including the experience of getting a bunch of cash with as few individual moves as possible).

Thank you for attending my Ted Talk.
 
5-Volt's husband is rarely ever home and kinda forgets about his son 9-Volt, which in turn makes him feel rather abandoned sometimes.
5-Volt still loves her husband but wishes he spent more time with his family.

Also, 9-Volt has attention deficit disorder and 18-Volt is dyslexic.
 
When Wario is "in shape", such as when he is treasure hunting as his main occupation, he is nearly invincible, but when he's not, like in WarioWare, he is sort of weak.
 
5-Volt's husband is rarely ever home and kinda forgets about his son 9-Volt, which in turn makes him feel rather abandoned sometimes.
5-Volt still loves her husband but wishes he spent more time with his family.

Also, 9-Volt has attention deficit disorder and 18-Volt is dyslexic.
I always liked to imagine that 5-Volt looked just like 9-Volt as a kid, then became a teen mom after she shot up and was hot all of a sudden. 9-Volt's helmet used to be hers.
 
Plausible, especially the helmet part. It's aldp shown throughout the games that she also likes games quite a bit too, so maybe 9-Volt's love for games and Nintendo came from 5-Volt? As in, she gave all her consoles, toys, merch, everything to her son, thus resulting in the 9-Volt we know today, which was probably pretty similar to 5-Volt as a kid.

Nintendo really should give us some more lore...
 
Plausible, especially the helmet part. It's aldp shown throughout the games that she also likes games quite a bit too, so maybe 9-Volt's love for games and Nintendo came from 5-Volt? As in, she gave all her consoles, toys, merch, everything to her son, thus resulting in the 9-Volt we know today, which was probably pretty similar to 5-Volt as a kid.

Nintendo really should give us some more lore...
Well, that's also quite likely, considering my love for Nintendo was sparked when my dad downloaded an NES emulator, GBA emulator, and a metric shitton of ROMs for the latter (there were a couple hundred for the NES one that I remember, but the GBA had thousands from both GB/GBC and GBA). I remember being confused at why the first two Wario Lands were in black and white, and because I couldn't read very well yet, had to memorize the order that the versions of Wario Land II in the explorer window came in so I could play the one that was in color. Interestingly, I don't remember having a ROM for 3, just WL, II, II in color, and 4... I disliked that WL1 Wario didn't have his cap, and disliked WL4 Wario's ugly jagged teeth. That was the main reason why I always opted for II when I played Wario.
On top of this, even though we had a PS2 at the time, I remember being blown away by the graphics in Super Mario Bros. 3-- this was in 2005, mind you-- and later on, we got an N64 emulator and was like holy shit dude looking at SSB64 (even though by this point I was already a huge player of Pac-Man World 2 and the first two Tak games on PS2), and my brain halfway exploded when I got to see Melee on the Dolphin emulator (funnily enough, that's where I learned about the relationship between X and Y axes).

tl;dr by coincidence I got to experience the entire evolution of console gaming in order despite being born in 2000.

So yeah, it's entirely possible. Also, the idea of a younger 5-Volt not knowing how to cope with all the sudden attention is adorable-- like she's got that helmet on and sees all these people, including other girls, checking her out, and just has no idea what the hell is going on.
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Well, that's also quite likely, considering my love for Nintendo was sparked when my dad downloaded an NES emulator, GBA emulator, and a metric shitton of ROMs for the latter (there were a couple hundred for the NES one that I remember, but the GBA had thousands from both GB/GBC and GBA). I remember being confused at why the first two Wario Lands were in black and white, and because I couldn't read very well yet, had to memorize the order that the versions of Wario Land II in the explorer window came in so I could play the one that was in color. Interestingly, I don't remember having a ROM for 3, just WL, II, II in color, and 4... I disliked that WL1 Wario didn't have his cap, and disliked WL4 Wario's ugly jagged teeth. That was the main reason why I always opted for II when I played Wario.
On top of this, even though we had a PS2 at the time, I remember being blown away by the graphics in Super Mario Bros. 3-- this was in 2005, mind you-- and later on, we got an N64 emulator and was like holy shit dude looking at SSB64 (even though by this point I was already a huge player of Pac-Man World 2 and the first two Tak games on PS2), and my brain halfway exploded when I got to see Melee on the Dolphin emulator (funnily enough, that's where I learned about the relationship between X and Y axes).

tl;dr by coincidence I got to experience the entire evolution of console gaming in order despite being born in 2000.

So yeah, it's entirely possible. Also, the idea of a younger 5-Volt not knowing how to cope with all the sudden attention is adorable-- like she's got that helmet on and sees all these people, including other girls, checking her out, and just has no idea what the hell is going on.
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I still do like this idea. I can't believe it's already been three years. And believe you me, that's because this was the thing that caused me to realize I literally am as good as drunk when I'm tired. The initial post isn't that bad, though.
 
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"Sweetie, I didn't get tall until I was like, uhhh 16, I think. 17? I dunno, it's been a while."
"Seventeen?! That's like a million years from now!"
"Yup, you'll be an old man."
"...I remember I was a really late bloomer, though."
*Starts stroking chin* "Arr, yes, it was the summer of '93, it was... I went from almost exactly your height to 5'0 in less than a year!"
*squint, one-sided grimace* "It was a darrrk and haarrrible time fer all..."
"did you sound like a pirate"
*nodding head with eyes closed* "Aye..."
You can't fathom how much I love the idea of some little story snippet or one-shot or whatever where you're led to believe that you're following 9-Volt around, but at the very end we find out that this kid in the helmet is really an infantile 5-Volt.

It's like the beginning of Toy Story, where you think the photos are Andy but the pictures are actually of Andy's father, of whom he is the spitting image (to clarify further, the house is Andy's grandparents' house, Andy's dad is Andy Sr., he's the one who owned the toys, his Woody doll thought that Andy Jr. was Andy Sr, that's why all of Andy's toys except for Buzz are old as shit, etc. Really cool plot twist, only found out a few months ago).
 
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To clarify, you can't fathom how much I love the idea of some little story snippet or one-shot or whatever where you're led to believe that you're following 9-Volt around, but at the very end we find out that this kid in the helmet is really an infantile 5-Volt, and we get some family photo on the wall timeline thing, best summarised as:
"Hey it's 9-volt
"wait why is 9-volt taller
"wow that's a lot taller, who's that guy
"A child has been born and is being held in a weary, gown-clad 5-volt's arms. The newly-made mother smiles teary-eyed into the camera, eyes glistening behind a green visor
"the newborn sleeps, the helmet can be seen resting upon a nearby table. Awwww, sleepy baby
"the child is a bit older, crawling around, is now wearing the helmet
"5-volt and the child are now standing side by side"


It's like the beginning of Toy Story, where you think the photos are Andy but the pictures are actually of Andy's father, of whom he is the spitting image (to clarify further, the house is Andy's grandparents' house, Andy's dad is Andy Sr., he's the one who owned the toys, his Woody doll thought that Andy Jr. was Andy Sr, that's why all of Andy's toys except for Buzz are old as shit, etc. Really cool plot twist, only found out a few months ago). i edited this years old post so i won't want to kill myself as much
I'm going to wake up and regret doing all this shit at two in the morning doing this, for the rest of my life
 
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