Stay a while and listen. Hear the tale of Robbie Rotten, mastermind rogue.
I was playing a variant human mastermind rogue named Robbie Rotten (yes, THAT Robbie Rotten) who had the Actor feat and a high charisma. Robbie was and is still my favorite PC because he was great at both shenanigans and combat. This is an account of one of his greatest feats.
WARNING: SPOILERS AHEAD
The campaign was Curse of Strahd. My party had to kill the powerful hag Baba Lysaga. However, we found out that the hag had a fondness for the Dark Lord Strahd von Zarovich. As a "villain number one", I disguised myself as Strahd and disguised my partymates as his vampire entourage. We came to Baba Lysaga's hut which was surrounded by her minions. The following was an account of what happened…
Me: Baba Lysaga, it is I, the Dark Lord!
Baba Lysaga: Oh my! What brings you here, my lord?
Me: I've come to claim you as my bride. I realized that I'm into matured women and I am in love with you! Come, let us marry!
Baba Lysaga: *blushes*
After successfully seducing her with a very high roll and then tricked her into drinking poisoned wine, I carried her to her hut when she became ill. Inside the hut, my party slaughtered her and we retrieved the quest item.
Second encounter. My party and I had to deal with some evil druids who possessed another quest item. Again, we were disguised with me as Strahd. The druids, especially the Archdruid, would've found me out but thanks to carefully selected words, Master of Intrigue, Actor feat and a very high roll, they believed that I was the Dark Lord himself.
Me posing as Strahd: I believe that you have a (quest item). I'd like to have it.
Druid: My lord, how did you know?
Me: I am the Dark Lord. I have eyes and ears everwhere in Barovia.
Druid: Ah yes of course! Please forgive us!
The druids were thoroughly convinced that I was Strahd and gave us the quest item. Using Insightful Manipulator, I found out who the strongest among them. I convinced him to accompany me and my party to a secluded place so I can "bless" him. The cleric did a made-up ritual as a build-up and then the barbarian (disguised as a slave girl) decapitated the Archdruid. Using a magic item we looted from the Archdruid, the party druid summoned minions to massacre the rest of the druids.
Next, we had to look for an NPC in the town of Valaki. Unfortunately, the villagers were brainwashed into an angry mob seeking to hunt us down. I disguised myself as the famous fortuneteller Madame Eva and I disguised my partymates as Vistani assistants and companions. The villagers spotted me and I told them that I would tell their fortunes to distract them while the rest of my party seeked the NPC. All villagers failed their insight checks on me except for one little boy.
Boy: She's not Madame Eva!
Me: (Thinking: Why you little-!) My child, come closer so I can read your fortune.
Me: *holds child's head and then pretends to go into a psychic trance* Oh! You will receive a lot of candies and toys in the future! *boy became interested but I get glared at by boy's parents*
Me: Ah! As long as your parents give you candies and toys, you will become a great politician! *parents looked much happier*
After 1 minute of conversing with the boy, I knew that he wanted to become a knight. Thanks, Insightful Manipulator.
Me: Ah! Not only you will become a politician, you will become a knight of the highest order! *boy became a true believer*
That was the last part of the adventure. The whole thing was 99 percent shenanigans and 1 percent combat. After that chapter, one of my partymates now believes in the power of shenanigans thanks to Robbie Rotten's lesson in trickery that will go down in history.