I played Willy Beamish again recently and I felt like some aspects of it held up remarkably well.
The graphics are low resolution as hell (320x200, the usual), but the style and relatively smooth animation quality help alleviate that a lot.
The writing has both the highest highs and lowest lows. The plot in general is pretty good, being driven by characters and their personalities. Willy wants to get to the Nintari championship and his actions are mostly driven by that motivation, and diabolical shenanigans in the background are being driven by the main antagonists. The antagonists are very cartoony, but in a very intentional way where you don't get to see their motivations and backgrounds a lot, but they still fill a kind of stereotype based on real personalities, those being corrupt corporate executives and schoolyard bullies.
Willy himself is the most well rounded character. He's kind of a shitty brat, but in a realistic way where he's just self-absorbed in a way kids that age are, and his negative character traits are juxtaposed by a childlike innocence and doing nice things for people despite himself just to keep on their good side. Willy's relationship with his younger sister is a great example of this, because he just wants to play Nintari and hang out with his friends, so he kind of thinks of her as nuisance because his parents make him spend time with her, but he still plays nice with her to keep the peace.
A couple of characters are kind of paper thin stereotypes though, particularly Willy's trophy wife mother and airhead valley girl older sister. There are some others, but those two stand out in particular because Willy, his dad, and his younger sister seem like a nice, well-rounded bunch with good chemistry.
Where the game doesn't hold up so well is all the trial and error and game overs. There's a whole bunch of dialogue trees where you basically have no idea which choice will be instant death, and I think at some points you can screw yourself over by missing an item hunt and being irreversibly stuck later.
Oh and the voice acting was pretty good.
why am i making a willy beamish effortpost in 2016 oh god what am i doing with my life