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In Richard III, George, Duke of Clarence and brother of King Edward IV and Richard, is brutally assassinated after Richard has him sent to the Tower of London. Two henchmen enter and brutally stab George repeatedly; then, in order to ensure that he is dead, these murderers place George into a cask of wine which contains two hog heads, as well. To add to the grisliness of these scene, the Duke has previously asked for a cup of wine and one murderer says, "You will have wine soon enough."
Another addition to the horror of the death of the Duke of Clarence is the fact that his acts of loyalty to his brother are repaid by the treacherous Richard in this murderous manner. The scene in Act I of the duke's death, thus, points to the unconscionable character of Richard.
The word 'grizzliest' immediately (if perversely) calls to my mind the scene in The Winter's Tale where Antigonus is chased and killed by a bear. While it happens offstage--"exit, pursued by a bear" (III.iii.58) is probably the most famous stage direction in Shakespeare--when staged for sympathy and/or grotesquery, the audience is suitably horrified by Antigonus' grim end. The loyal Antigonus, after all, risked his life to save the infant Perdita's.
His death also marks a change from the first act to the second act, from the all too human error that results in Mamillius and (we are led to think) Hermoine's deaths to the violent but natural processes of the wider, wilder world.
Titus Andronicus is pretty grisly. Act II, scene 3 is just borderline demented. The bad guys plan on raping and murdering the fair Lavinia. First they murder her husband Bassianus, and then plan on using his dead corpse for a cushion when they rape Lavinia:
"Drag hence her husband to some secret hole / And make his dead trunk pillow to our lust."
Even though Lavinia doesn't technically die, her attackers Chiron and Demetrius, rape her and then cut off her hands and tongue so she cannot tattle on their misdeeds. When she reappears in scene four, her mouth is a "crimson river of warm blood" (II.iv). Ew.
Then in Act V, scene 2, Lavinia gets her revenge when Titus slits Demetrius' and Chiron's throats, and Lavinia catches their blood in a big bowl. Titus announces that he is going to bake his daughter's attackers into a pie, "And in that paste let their vile heads be baked" and feed it to their mother, which he does in the final scene of the play. The final scene, the banquet with the human pie, is a total bloodbath.
Titus Andronicus is definitely the most gory of all of Shakespeare's plays.
I would like to add, that along with the death scenes so gruesomely created and acted out in the amazing Shakespeare play Hamlet, that one we might consider is the scene alluded to in the play.
Sleeping within my orchard,
My custom always of the afternoon,
Upon my secure hour thy uncle stole,
With juice of cursed hebenon in a vial,
And in the porches of my ears did pour
The leperous distilment; whose effect
Holds such an enmity with blood of man
That swift as quicksilver it courses through
The natural gates and alleys of the body,
And with a sudden vigour doth posset
And curd, like eager droppings into milk,
The thin and wholesome blood: so did it mine;
And a most instant tetter bark'd about,
Most lazar-like, with vile and loathsome crust,
All my smooth body.
Thus was I, sleeping, by a brother's hand
Of life, of crown, of queen, at once dispatch'd:
Hamlet Act 1 Scene 5
As a gruesome scene, the assassination of Julius Caesar has to rank in the top five. When Antony brings the body of Caesar before the crowd, the crowd is shocked by the horrific nature of his wounds:
Look, in this place ran Cassius' dagger through;
See what a rent the envious Casca made Through this the well-beloved Brutus stabb'd;
And as he pluck'd his cursed steel away,
Mark how the blood of Caesar follow'd it,
As rushing out of doors, to be resolved.
Caesar was totally unprepared for his attack. He had been warned by several people to be careful. However, Caesar felt he was above the normal acts of men. As he is surrounded, Caesar is completely overwhelmed by the many assassins.
When the assassination was done, Caesar had over 25 stab wounds from the top of his head, his hands, and his body.
While I've never been a fan of Claudius, I've always found his death quite gruesome (and fitting). His plan to kill Hamlet both works and is used against him. He has a plan to give Laertes a poisoned sword and a back up plan to poison the wine. Once Laertes realizes that they are both doomed to die, he confesses the "villany" is present and that "no med’cine in the world” will help them to Hamlet, and he tells all about Claudius' plan. Urging him to “Follow my mother" Hamlet stabs his uncle with the poisoned sword and forces him to drink from the poisoned wine.
It is ironic that Claudius' plan is the source of his gruesome death.
Some of the bloodiest deaths take place in Macbeth.
Macbeth is beheaded by Macduff, which is pretty gross.
I know this is not likely what you are asking, but the scene that most captures my imagination is actually Lady Macbeth's death in Macbeth. She is said to have killed herself, but how? It does not happen on stage.
Macduff's entire family, including his young son, is killed by Macbeth's murderers.
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