Darkest Moments in Game of Thrones

The Top Ten
1 Princess Shireen Is Sacrificed
2 Joffrey Forces Sansa To Stare At Her Father's Severed Head
3 Meryn Trant Rapes And Beats Underage Prostitutes
4 Ramsay Cuts Off Theon's Penis And Sends It To His Family
5 Ramsay Rapes Sansa
6 Joffrey Tortures Prostitutes For His Own Amusement
7 Arya Kills Walder Frey's Sons, Bakes Them Into A Pie, And Feeds It To Him
8 Crastor Has Sex With His Daughters And Kills Any Son He Fathers
9 The Mountain Smashes Oberyn's Head
10 A Frey Soldier Repeatedly Stabs Talisa In Her Stomach At The Red Wedding, Killing Her Unborn Child

I would say the Red Wedding in general.

The Contenders
11 Jon Snow is Crowned King of the North
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