Interrupting a Tender Moment via Improbably Aimed Barrels [D&D Game Tales]

So. I'm Dming a group and this night we had an unusually large session. We just added in a new PC who will be joining us for the remainder of the campaign and a visiting friend who was a guest character for the night.

The PC had successfully managed to get into the favor of a local Baron, who invited them all to dinner. The guest was playing a premade character, the bastard son of the baron who had just returned home hoping to earn his asshole father's respect.

So dinner goes fine, the Baron is a smarmy asshole and a monster attacks. After a very tough fight the PCs are victorious. Then things get weird. The son goes to the Baron to tell him of the victory and they have a moment. Fearing his father losing interest, the son then lied and told the baron that there was a treasure trove of a caravan down waiting for him at the foot of the 200ft tall hill the Baron's castle is located on. The pair start walking down, the son the whole time trying to think of some way to get out of the lie he made.

The other PCs follow them outside and stop at the top of the hill, and one of them says, "You know, that Baron was a real asshole. Be a real shame if something heavy happened to fall on him from this high up."

A quick investigation later and they find a 200lb barrel of tar in a barn. One of the PCs, who is both good aligned and canonically an idiot, tries to stop them and gets knocked the fuck out and tied up. The remaining PCs manage to lift the barrel, carry it to the top of the hill, and then toss it.

Meanwhile, the son is nailing his charisma rolls against his father and soon has him eating out of his hand. They get to the bottom of the hill and the father for the first time in the son's entire life tells him he's proud of him.

And then a 200lb barrel of tar lands on the Baron after falling 200ft, instantly killing him.

What follows is a roaring rampage of revenged that killed one PC and nearly killed another, so in the end we decided to take everything after the boss fight as a non-cannon fever dream the whole party had.

It was probably the hardest I have ever laughed during a D&D session in my entire life.

I love this game.