hmm craziest video
maybe not the craziest (and probably far from awesome) but I got a few that stuck in my mind like:
(friendly warning, some of these videos might not be appropriate for some viewers so.. yeah.. keep that in mind)

• the song Secrets of Wysteria by Stempianist I think?
• the Don't Hug Me I'm Scared series by.. well.. "Don't Hug Me .I'm Scared"
• the Flamingo song or whatever they are called, the original song is this one I think.
• also if you search "important videos" on YouTube, you'll probably find this playlist

well that's some weird videos I can remember, here are some other few which I think is awesome (maybe you are interested):

• A TEDx talk titled "How to Magically Connect with Anyone" by Brian Miller, a magician
• a 1 hour video of Richard Turner (also a magician, but this one's blind, he's really cool), if that's too much for you there's another video of him when he visit the "Fool Us" show by Penn & Teller, he gave an amazing performance in the show.
• hmm what else, maybe a Life Lessons From 100-Year-Olds?

some other videos I prefer not to share because it might be a boring video anyway
so that's that.. I hope you have fun with it

https://www.youtube.com/watch?v=6QFwo57WKwg

Challange accepted :)

WTF videos
Olympic Swimming
This is... Japan World Cup 3
Ski Jumping Pairs
Ultimate Muscle Roller Legend
[The Last Dolphin Citizen]https://youtu.be/IfXjTUIdQEY)
The Choir
AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHHHHHHHHHHHHH - how to make game more epic by lowering gravity
Video Game Abomination - if you want lost hearing check "I'm han solo"
how 2 montage
Boss Coffee - Rainbow Mountain Blend feat. Tommy Lee Jones - turn on subtitles
Is This War Face Big Enough?
Top Soccer Shootout Ever With Scott Sterling (Original) - there is version with voleyball too :3

Funny
SURICATE - The Superheroes Hangover - turn on english subtitles
HAPPY SOULS(You Reposted in the Wrong Developer Update
Jenko's Epic Split- behind the scenes from film 22 Jump Street
Ascension of the Jackdaw - bugs in games are always funny :)
Teachers be like (@VineCreative)
ThePruld I'm into the abyss - turn english subtitles on
Are those reebok or nike (subtitles)
Sir Ian McKellen (Gandalf) falls asleep on the Hobbit set
The Casul's Guide to High Wall of Lothric Dark Souls 3 - whole series
Why wearing cone-shaped metal hats is a bad idea.

Random awesome videos
Phillips commercial with song The Black Angels - Black Grease
Turbulence Saxxy Awards 2015 Best Overall
Snoop Dogg, David Beckam and Star Wars team up for Adidas
Harry Potter and the Ghetto Street War
SUPER-HERO-BOWL! - TOON SANDWICH
Rockin'1000 - Seven Nation Army | That's Live 2016 - listen this only if you have nice audio

Random
I just wanted to put this somewhere xD
The Patient Gamer