This skit was NOT meant to be canon. But somehow it ended up being canon as we find out Kakashi and Tobi/Obito are actually best friends.
Most of the stuff used in this skit were trending memes back in 2008 and ealier. You'd have to travel back in time to understand. When YouTube was first created their most viewed video was 'Evolution of Dance', this skit was partially inspired by that, and Spongebob souljaboy video along with Avril Lavaigne's - Girlfriend were also most viewed videos back in those days. Caramelle Dancing was also big during that time in the Anime community.
This is our Anime North 2008 skit contest masquerade. Skit Entry #6
Won "Best in Novice Division" at Anime North 2008
You can guess who I was cosplaying LOL.
0:30 - Naruto Shippuden OST
0:40 - ??? Naruto OST
1:06 - Carl Douglas - Kung Fu Fighting
1:20 - Akatsuki Theme
1:34 - ??? Naruto OST
1:48 - MC Hammer - Everybody Dance Now
2:00 - MC Hammer - Can't touch this
2:26 - Sugarhill Gang - Apache
2:47 Peanut butter jelly time
2:58 - Caramell - Caramelldansen
3:10 - Dragonball Z theme
3:25 - Suzumiya Haruhi - Hare Hare Yukai
3:42 - Lucky Star
4:00 - Soulja Boy - Crank That
4:40 - Naruto OST
4:54 - Naruto OST - Sexiness
5:07 - Backstreet Boys - Show me the meaning of being lonely
5:19 - Avril Lavigne - Girlfriend
Kakashi - Anonymous
Tobi/Obito - Anonymous
Deidara - Nat
In case you couldn't guess. I was Itachi on the stage btw, just for this skit.
Video credits go to: icosplay for filming