It can be anything very dramatic, unpredictable or surprisingly scary/disturbing, also you can pick from any media you want whether it be comics, movies, cartoons and games.

My top 5 picks would be something like:

1. Spider-Man: The Animated Series (1994) - Spider-Man transforming into Man-Spider and the entire episode that it appears in, titled ''Duel of the Hunters''. Seriously, when I first saw these episodes at 8 years old, Man-Spider scared the absolute hell out of me.

2. I'm kinda cheating with this one, because it's two moments but they take place in the same story arc:

Web of Spider-Man #31-32, The Amazing Spider-Man #293-294, and The Spectacular Spider-Man #131-132 - Kraven's Last Hunt, one of the best Spider-Man stories ever written, the two shocking moments I'm talking about is Kraven ''killing'' Spider-Man and assuming his superhero identity and Kraven at the end of it committing suicide.

3. Spider-Man Edge of Time - The Death of Spider-Man, it was a hard decision to make between which Spider-Man Death to choose from, but for me personally I liked how it was handled in this game the most.

4. The Amazing Spider-Man #509-514 - Sins Past, yeah when I first found out about this I was genuinely shocked and kinda disturbed, obviously the most shocking moment in this story is Gwen Stacy having sex with Norman Osborn.

5. Spider-Man (2002) - Spider-Man Vs Green Goblin Final Fight Scene, the reason why I'm putting this is simply because of how brutal & dramatic it is and how you feel scared for Spider-Man, my god this made Green Goblin look like such an intimidating foe for Spidey and to this day, it remains as my most favorite Fight Scene out of every live action Spider-Man movie.

- The Lizard killing his son in Shed (I think)

- Morlun eating Spider-Man’s eye then giving him an epic beatdown in the JMS run. (was very young when I read this, was surprised)

-Mary Jane clone evaporating in the animated series.

- Spider-sperm giving MJ cancer (this was more lol moment tho)

- Carnage Octopus in the PS1 game, stuff of nightmares.

@fromapov: We don’t talk about Sins Past...

1. Peter revealing his identity in Civil War
2. Sin Past. Lol
3. One More Day

@rabumalal: Sorry, I couldn't help it.

I wouldn't say much in Spider-Man "shocks" me, but they do make me roll my eyes at just how badly they can screw up nice things

-Peter's parents are ROBOTS

-Ben Reilly's death

-Ben Reilly's return as a bad guy

-The end of the recent Scarlet Spider series (even Marvel pretends it didn't happen)

-The miscarriage of MJ (though this is ignored in the Spider-Girl timeline)

-MC2 Peter's death in Spider-Verse (thankfully it turned out to be temporary)

-Black Cat's heel turn, she almost killed Aunt May.

-MJ of all people being a bitch during the last ten years in general

-Sins Past is great if you hate Gwen, Sins Remembered is worse

-Aunt May being revealed as alive and well after her meaningful death in ASM 400 (again, something Spider-Girl ignores)