What is the most legitimately cruel act throughout the franchise?

The most cruel act was implementing motion control mini games into Super Mario Galaxy.

I never want to do another rolling ball level again.
 
Sling Pod Galaxy is cruel to Mario. What did Mario ever do to deserve this?
 
Forgot about the entire Mario Party series

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Look how much fun these characters are having! Don't you want to join?
 
You run the risk of getting brain hemorrhages and a massive blood leak in the stomach from this minigame, but it's totally worth it to see that look in Wario's face when he's knocked away.
 
If we're doing side games too, WaaaaaAAAAAAAAAAAAAHluigi's exclusion from Mario Kart 7 is definitely a contender
 
When you're forced to watch the Toad's have their life force slowly drained in PiT is always pretty depressing.
 
ArchagentEverlasting said:
When you're forced to watch the Toad's have their life force slowly drained in PiT is always pretty depressing.
That description reminded me of Colour Splash, which featured the Toad being sucked out of its colour by Shy Guys.

Thank you for reading.