I have no idea how to describe this properly. I have no clue.

The best way to explain is by watching the footage I made of this weird bug/glitch:
My perspective: http://youtu.be/byEXmq9bzp8
Eniallator's perspective: http://youtu.be/Ro-K4YCyD1U

The command I used:

/summon Skeleton ~ ~1 ~ {Equipment:[
{id:261,tag:{ench:[{id:50,lvl:1}],
{id:301,tag:{display:,}}
{id:300,tag:{display:,}}
{id:299,tag:{display:,}}
{Damage:3,id:397,tag:{SkullOwner:eniallator],}}
CustomNameVisible:1,CustomName:"This is Bob"}

No idea what's wrong, anybody knows?