There are many ways to die in the Marvel universe, and Deadpool has experienced pretty much all of them. Shame that absolutely none of them can actually keep him down, then.
Yes, the main running gag with the merc' with a mouth has always been that his healing factor is so advanced that absolutely nothing can permanently put him out to pasture. Despite the constant attempts by the most powerful villains and - sometimes - heroes of the Marvel universe, Deadpool just won't freaking die.
And with those attempts being so numerous, it only makes sense that some of them would be downright crazy and ridiculous. Whether it's subjecting him to injuries straight out of a Tex Avery cartoon, torturing him with unusual methods, or using their powers in the most brutal ways imaginable, Wade has been through a lot, and a lot of it is just plain silly.
Needless to say, these attempts on Deadpool's particularly stubborn life are memorable for both their creativity and for just how god damn silly they are.
10. Having An Anvil Dropped On His Head - Deadpool Team-Up #885
Deadpool is already the Marvel universe's brutal, bloody equivalent to a Looney Tunes character, so why not take that to its next logical step?
In Deadpool Team-Up #885, Deadpool goes to meet someone he met online, who tells him to meet them in a dark, dangerously suspicious alley. So of course Wade does it without batting an eye.
He doesn't even raise an eyebrow when he sees a big white X in the center of the alley. After all, why focus on that when there's a four leaf clover ripe for the picking?
Sure enough, Deadpool bends down to pick it up, narrowly missing the anvil tied to a string that swings harmlessly over his head without him even knowing it was there. However, the laws of physics are a tricky mistress, so when Deadpool stands back upright to praise his lucky find, the anvil makes its mark on its return swing, going right through his head and smearing Wade-brain-juice all over the likely already disgusting alley.
Deadpool then gets back up a minute later, finding whoever was behind this more rude than anything else.