First of all, if you’re part of my campaign, stop reading this right now, because spoilers.

Hello, everyone. In our group’s last session, the PCs encountered an underground Drow colony that they had been tasked to make peace with. As a spur-of-the-moment decision, I made the Drow accept the adventurer’s help, on the condition that they must pass 5 challenges, one for each party member. I improvised the first two challenges, which were a duel atop a moving Purple Worm, and an interaction with a Doppelgänger, both of which I think went well. However, I still need three more challenges for the next session, which is why I’m asking for the creative minds here to help brainstorm them. The remaining party members are an animal hunter ranger, a fighter who punches things, and a bard who sings about everything he comes across. Suggestions?

I run a Roman-based campaign so I have done a lot of reading up on the real-world gladiator events. Romans did chariot races (not sure that will work for you), but they also did "beast hunts." They would let loose a bunch of wild animals and humans hunters and the idea was the fans would watch people doing "real hunting." (Or as real is it can get in an arena.) I think that works for a hunter ranger - let him/her do a beast hunt.

Fighter, I would think a straight-up mano-e-mano gladiator duel with the current "reigning champion" would work (do that one last).

Not sure about the bard... I'll think more on that and see if I can come up with something.

Quote from BioWizard >>

I run a Roman-based campaign so I have done a lot of reading up on the real-world gladiator events. Romans did chariot races (not sure that will work for you), but they also did "beast hunts." They would let loose a bunch of wild animals and humans hunters and the idea was the fans would watch people doing "real hunting." (Or as real is it can get in an arena.) I think that works for a hunter ranger - let him/her do a beast hunt.

Fighter, I would think a straight-up mano-e-mano gladiator duel with the current "reigning champion" would work (do that one last).

Not sure about the bard... I'll think more on that and see if I can come up with something.

 I like the idea of a simulated hunting ground... yeah, I’ll probably end up doing that.

The one problem with a gladiator duel is that the fight on top of the Purple Worm was basically that. I could figure out some ways to make it unique, though. Maybe have some weak points on the champion or something.

Thanks for the suggestions. 

Does the fighter have athletics? What if it is some kind of an athletic event, like a Decathlon? Shot put, high jump, etc. Maybe some kind of a skill challenge, he needs 6 successes before 3 failures. Every time he gets a failure his competitor scores higher than he does. Every time he gets a success he scores higher. If he wins the challenge, he wins the Decathlon.

You could make the Decathlon more dangerous -- I'm thinking of the old PC game, "Cave-man Ughlympics." They had things like the "Dino vault" where you had to fault over a dinosaur and if you failed it ate you. High-jump over a Giant Crocodile or something instead of a bar...

Yeah, I think he does. My original idea was actually something like this- a tug-of-war or something. A series of different challenges would probably be better, though.

Quote from BioWizard >>

You could make the Decathlon more dangerous -- I'm thinking of the old PC game, "Cave-man Ughlympics." They had things like the "Dino vault" where you had to fault over a dinosaur and if you failed it ate you. High-jump over a Giant Crocodile or something instead of a bar...

 (Insert evil DM laugh here.) 😈

 (Insert evil DM laugh here.) 

My work here is done.

I think the gold standard bard challenge is the 16-bar freestyle.  There's an inherent problem with people dice-rolling performance skills, it's just painfully unsatisfying.  If your player actually likes singing about stuff around the table, and no one else will mind letting them get away with it, just have them sing a song and don't bother rolling anything.  

Otherwise, maybe a contested performance check as they're forced to cut heads with a drow musician.  First one to five successes wins and if your player sweeps all five, they get some kind of bonus.

Yes I am having trouble coming up with a good bard singing challenge. Still pondering... But I agree that just dice-rolling performance is not super inspiring.

What if it's something like the dragon-egg challenge from Harry Potter, combined with Fluffy? The 3-headed dog that is put to sleep by song... and the dragon egg you have to get without the monster killing you. What if the Bard has to get a golden egg from a dragon that wants to protect it, and has to charm/sing/etc. his way through it?

Still mostly rolling performance, I guess... but you could make it a skill challenge. 5 successes before 3 failures or something. Each time he fails the dragon gets mad and chomps at him, maybe he takes some "singe" damage. He success he gets closer to the dragon. Eventually he sings it to sleep or distracts it enough that he can get the egg and get away.

Maybe you could use multiple skills - performance, deception, intimidation, acrobatics (to get the egg) -- play on the many skills of the bard. Allow him to use maybe a spell slot and arcana check to indicate using an illusion spell, that kind of thing.

Btw, the player sings the recap of the previous session at the start of every session. So I think he would prefer an IRL singing challenge, in comparison to a few abstract dice rolls.

Here is a list of activities:

1: Animals/group of small monsters

2: One large monster

3: Team of Gladatiors.

Or, you can do the Olympics! The group can prove their worth in feats of strength and prowess, and are freed when they have completed their tasks.

For a musical challenge, I have toyed with the idea of a "magical guitar hero" style challenge. The premise was that the musician would stand on a platform surrounded by shields scattered on the floor, and plays a song (repeat performance checks), and each note played lifts a magical shield which blocks an axe/dagger which is launched from holes in the walls.

The visual would be the bard playing this epic song in time to block every thrown weapon, which would be awesome.

the mechanics of it in an actual game would, regrettable, be just kinda rubbish.

For the hunt, I would recommend a twist - tell the ranger they have to beat the other Drow in the arena (perhaps 4 others), but don't elaborate. When they get in there, the first thing they see is >insert a significantly too powerful beast here< killing one of the Drow, and they realise that they are the ones being hunted - last one standing is the winner. Turns into survival skills and stealth, rather than tracking and killing. Perhaps give them several checkpoints to go through whilst avoiding being caught.

A rhyming challenge could be a good one for the Bard, especially if the player is inventive with lyrics. Have them engage in (functionally) a rap battle with an enemy bard, with each round dealing vicious mockery to the loser. I believe the official name is "Flyting", and it was invented by the Norse. It's a "ritualistic, poetic insult exchange". You can write up or google a load of them ahead of time to populate a random table (or just to give yourself prompts), they'll have to do it on the fly. Make sure that you describe the Drow they are facing thoroughly, so they can give them a sufficient roasting - give them a big nose, squinty eyes, all sorts of things to pick up on based off a perception check.

For the fighter, the Drow aren't renowned for fighting fair - perhaps throw them a curve ball by having them have to face an enemy which is almost impossible to hit - a Drow assassin who dodges almost everything and is just playing with them. one good hit and they go down, but the fighter might have to face the drow ridiculing them as the assassin dances around playing the crowd. Make it fists only, give the Drow an AC of about 22 or so (make them roll 18+ to hit them) and just have them open-hand slap the fighter to the roars of the crowd,  d4-1 damage per slap (minimum 1). After some playing, have them land a proper blow and deal some more decent damage. Perhaps work in a mechanic of your own where if the Drow gets riles up through insults they lose focus and their AC drops, so the fighter could try taunting them for a better chance to hit.

A medieval rap battle would be perfect, thanks.