D&D 5E Any cool Skill Challenges you've run in 5e?

[AnotherGuy]

An Appeal to the Mad Mage for a Long Rest.
Our table runs a pretty harsh recovery system by 5e standards, and the party found itself quite depleted and in much need of a Long Rest as they were heading to take-on Netherskull, the Death Tyrant of the Obstacle Course level of Undermountain. I was using Wyatt Trull's DotMM Companion from the DMs Guild, where Halastar runs the entire operation like some theatrical piece of entertainment for himself and others.

Anyways between sessions, the PCs came up with an idea to request (from Halastar since they knew he was watching) for a 24 hour respite from the dangers of Undermountain, including the regional affects of the Death Tyrant which they were hunting. I thought it was a great idea, considering the way I had roleplayed Halastar up until that point.
So they made a broad appeal and sure enough the Mad Mage appeared betwixt them, amused by their request.

Since it was between sessions I had time to come up with an idea of how I wished to run it. Skill Challenge seemed the obvious choice for me.

I quickly drew from the top of my head 10 possible appeals/courses of action the PCs could take, with various DC's and Halastar's possible retorts. The retorts were meant for fluff before the argument would be made via the roll. The PCs were free to come up with their own ideas of course these were just the ones I expected them to throw at me and I would match them up to the closest as they came.
I view Halastar as someone who becomes bored quickly and with some exaggerated version of ADD, so I had him dismiss PCs who wanted to appeal consecutively, claiming they were hogging the spotlight or that he was bored of them or their face. That way it couldn't be the same person (with the high modifier) doing the talking/rolling all the time. They (the party) did fall for that loading one character with all sorts of CHA boosting bonuses. I have done something similar to them before so they should have learnt their lesson.

Appeals/Courses of Action
1 – Appeal to his Ego DC 10 (The appeal to his Ego should be the first, if not the DC of all checks are increased by 1)
2 – Appeal to Fairness of the Competition DC 15, But my dear the competition thrives on unfairness
3 – Appeal to the enjoyment of the Crowd DC 15, You're stating that you know better than I as to what the audience desires?
4 – Appeal to the Heroes worth* DC 15, Exactly, it is your worth that makes it exciting
5 – Appeal for Love** DC 13, A noble cause and yet, it is unrequited which makes it all the more sadder
6 – Appeal for the Continuation or Lengthening of the Game DC 15, Is that your plan with the Dragon Cult, to propose an extension?
7 – Offer a Gift or Negotiate Terms DC 20, History has shown you to be unreliable or unwilling participants, So no I won't be falling for that.
8 – Threaten the Wrath of the Council* on Undermountain and Him should they fall DC 20, Maniacal Laughter
9 – Make the case that the Heroes Loss would be bad for Undermountain DC 15, So integrity of the game be damned?
10 – Dare him, their Best against his Best, What is he afraid off? Call his Bluff DC 15, Maniacal Laughter

MECHANICS. 6 successes required before 3 failures.
Fail by 5 or more = 1 Failure.
Fail by 4 or less = Unconvinced. No Success, No Failure.
Natural 20 = Advantage on the Next Roll.
They each could make an Intelligence check once to come up with an idea of an appeal. The DC would be 10 + x, where x was the number of appeals that had already been made. The idea being the more appeals made, the harder it became for them to think of a different argument/angle.

RESULT.
The Party got 6 successes, 2 failures and 1 Unconvinced.
They were 12th level.

* Characters are the Heroes of Baldur's Gates (MiBG) and are currently the Council's Champions (ongoing ToD and SKT campaigns)
** Halastar kidnapped a PC (player left due to RL studies, and her kidnapping makes sense with her backstory), her retainer an NPC is in love with her. The NPC travels with the party. No. 5 was a given appeal by myself as DM roleplaying the NPC. Roleplaying Halastar as a bit of a romantic hence the DC was 13 and not 15.

 

[Shades of Eternity]

I love skill challenges.

I've used them for cattle drive involving thornslthers, to fix up a Bobcat, to perform an exorcism on a small bear and negotiating with a skull attached to a bomb to not explode in my last campaign.

 

[overgeeked]

Our table runs a pretty harsh recovery system by 5e standards, and the party found itself quite depleted and in much need of a Long Rest as they were heading to defeat Netherskull, the Death Tyrant of the Obstacle Course level of Undermountain. I was using Wyatt Trull's DotMM Companion from the DMs Guild, where Halastar runs the entire operation like some theatrical piece of entertainment for himself and others.

Anyways between sessions, the PCs came up with an idea to request (from Halastar since they knew he was watching) for a 24 hour respite from the dangers of Undermountain, including the regional affects of the Death Tyrant which they were hunting. I thought it was a great idea, considering the way I had roleplayed Halastar up until that point.

That's great. Makes me think of Mojo from Marvel Comics.

 

[beancounter]

An Appeal to the Mad Mage for a Long Rest.
Our table runs a pretty harsh recovery system by 5e standards, and the party found itself quite depleted and in much need of a Long Rest as they were heading to defeat Netherskull, the Death Tyrant of the Obstacle Course level of Undermountain. I was using Wyatt Trull's DotMM Companion from the DMs Guild, where Halastar runs the entire operation like some theatrical piece of entertainment for himself and others.

Anyways between sessions, the PCs came up with an idea to request (from Halastar since they knew he was watching) for a 24 hour respite from the dangers of Undermountain, including the regional affects of the Death Tyrant which they were hunting. I thought it was a great idea, considering the way I had roleplayed Halastar up until that point.
So they made a broad appeal and sure enough the Mad Mage appeared betwixt them, amused by their request.

Since it was between sessions I had time to come up with an idea of how I wished to run it. Skill Challenge seemed the obvious choice for me.

I quickly drew from the top of my head 10 possible appeals/courses of action the PCs could take, with various DC's and Halastar's possible retorts. The retorts were meant for fluff before the argument would be made via the roll. The PCs were free to come up with their own ideas of course these were just the ones I expected them to throw at me and I would match them up to the closest as they came.
I view Halastar as someone who becomes bored quickly and with some exaggerated version of ADD, so I had him dismiss PCs who wanted to appeal consecutively, claiming they were hogging the spotlight or that he was bored of them or their face. That way it couldn't be the same person (with the high modifier) doing the talking/rolling all the time. They (the party) did fall for that loading one character with all sorts of CHA boosting bonuses. I have done something similar to them before so they should have learnt their lesson.

Appeals/Courses of Action
1 – Appeal to his Ego DC 10 (The appeal to his Ego should be the first, if not the DC of all checks increase by 1)
2 – Appeal to Fairness of the Competition DC 15, But my dear the competition thrives on unfairness
3 – Appeal to the enjoyment of the Crowd D 15, You're stating that you know better than I as to what the crowd desires?
4 – Appeal to the Heroes worth* DC 15, Exactly, it is your worth that makes it exciting
5 – Appeal for Love** DC 13, A noble cause and yet, it is unrequited which makes it all the more sadder
6 – Appeal for the Continuation or Lengthening of the Game DC, Is that your plan with the Cult, propose an extension?
7 – Offer a Gift or Negotiate Terms DC 20, History has shown you to be unreliable or unwilling participants, So no I won't be falling for that.
8 – Threaten the Wrath of the Council* on Undermountain and Him should they fall DC 20, Maniacal Laughter
9 – Make the case that the Heroes Loss would be bad for Undermountain DC 15, So integrity of the game be damned?
10 – Dare him, their Best against his Best, What is he afraid off? Call his Bluff DC 15, Maniacal Laughter

MECHANICS. 6 successes required before 3 failures.
Fail by 5 or more = 1 Failure.
Fail by 4 or more = Unconvinced. No success, No Failure.
Natural 20 = Advantage on the Next Roll.
They each could make an Intelligence check once to come up with an idea of an appeal. The DC would be 10 + x, where x was the number of appeals that had already been made. The idea being the more appeals made, the harder it became for them to think of a different argument/angle.

RESULT.
The Party got 6 successes, 2 failures and 1 Unconvinced.
They were 12th level.

* Characters are the Heroes of Baldur's Gates (MiBG) and are currently the Council's Champions (ongoing ToD and SGK campaigns)
** Halastar kidnapped a PC (player left due to RL studies, and her kidnapping makes sense with her backstory), her retainer an NPC is in love with her. The NPC travels with the party. No. 5 was a given appeal by myself as DM roleplaying the NPC. Roleplaying Halastar as a bit of a romantic hence the DC was 13 and not 15.

I never did anything that involved, but I really enjoyed reading the OP.

 

[Professor Murder]

A key plot point in a game I ran was the PCs having to successfully complete a unicorn's tax return.

 

[Lyxen]

Any cool skill challenge I've run with 5e ? None. Any incredible roleplaying sessions where players tried, in character to convince NPCs to help them or even simply not to kill them ? I can't count.

For example, in Avernus, managing a small army as a coalition of enemy warlords and bluffing their way into a siege held by theoretically allied but practically opposed Princes of Hell.

Especially since, as you say, you "view Halastar as someone who becomes bored quickly and with some exaggerated version of ADD", why do you think he would have listened to more than one request ? Just make the right one or he just leaves. You have to choose wisely, and make a good case, but you have one chance, what's the logic of having 10 potential arguments ?

I appreciate the inventivity here, but this is a situation for inventivity by the players, for their characters, taking into account their personality and capabilities. Setting all the courses of action and allocating DCs in advance is exactly why it's good that Skill Challenges were not brought into 5e. 4e was very formal, and they fitted well within it, 5e is everything but formal and does not need them, just good roleplaying on all side and a quick ruling by the DM about a DC, if need be. Or, you could use the "Ignore the Dice" method of the DMG, where if the players have their character make enough of a good job of it, you don't roll the dice, and the same if they totally botch it.

P.S.: and I mean of course in character, a very glib player playing a character with 8 Cha and no social skill, and delivering a flowery speech in a commanding voice is botching it.

P.P.S.: There might be some cases where a skill challenge is appropriate, for example maintaining a ship afloat during a storm, because there are many technical things to do, but for social situations, especially one as simple as the example, count me out.

 

[Umbran]

I appreciate the inventivity here, but this is a situation for inventivity by the players, for their characters, taking into account their personality and capabilities. Setting all the courses of action and allocating DCs in advance is exactly why it's good that Skill Challenges were not brought into 5e.

So, if someone was having a discussion about a great sushi restaurant, and the craft of the chef, and asks folks what other great sushi they had recently, would you barge in to tell them they were wrong to have sushi, and should go to a pizza place instead? Because that's what this is like.

It is fine to have your preferences and opinions. But politeness calls for us to consider when we should insert those preferences, and when to let folks go ahead and talk about things that we aren't fans of unencumbered by our rejections. Let them talk about the thing they like, without telling them they were wrong to do it.

 

[Shades of Eternity]

oh yeah

I ended my game with a skill challenge that was a ping pong tournament.

The winning role was a critical history check where the character awed everybody about the history of ping pong that the opponent missed the last ball.