D&D (2024) What would Olive Ruskettle's class be in 2024?

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I would post in a forgotten realms sub-forum, but I don't see one?

Olive Ruskettle is a Halfling in the Azure Bonds novels that came out in the 80s. In the Novels she is essentially a Bard, and says she is a Bard, but because only Humans, and Half-Elves could be Bards in 1E the novels go to great lengths to make it clear she is really a Thief with some Bard-like attributes.

If you read the novels what do you think? Bard, Rogue, multiclass Bard-Rogue, something else? What subclasses?

One of our groups is looking at playing an Azure Bonds adventure and I am thinking of doing an Olive Ruskettle knock off as my PC.
 

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Bard with Urchin background would be fine. Olive never backstabbed anyone to my knowledge, so there's nothing in particular she'd gain from Rogue levels that wouldn't let her function as a skilled thief in 5e.

OTOH, other than singing so well she could keep Mist entertained, there's nothing that she gets from the Bard class that she couldn't do as a Rogue with an Entertainer background. But I'd probably make her a Bard since she'd get more use out of a high Charisma that way.

Though you could do something even wilder, Trickster Domain Cleric of Finder Wyvernspur?
 


After everything she has been through, she absolutely deserves to get her happy ending and be a Bard. So if you are statting her as what she might be NOW? Absolutely make her a Bard. Let her live the dream. If she came all this way and never managed to actually become a Bard, then I might shed a tear!

But since you are doing a knock-off in an established adventure, I assume you want to intentionally re-enact her character arc or make the same joke about "Why can't halflings be bards?" I would say Thief Rogue with the Entertainer background probably works best, as @humble minion mentioned.
 
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Rogue, Thief, Urchin
1ST Bardic Inspiration (d6), Expertise, Thief's Cant
2ND Cunning Action, Ear for Deceit, Eye for Detail
3RD Fast Hands
4TH Ability Score Improvement
5TH Bardic Inspiration (d8), Uncanny Dodge
6TH Expertise
7TH Evasion
8TH Ability Score Improvement
9TH Supreme Sneak
10TH Ability Score Improvement, Bardic Inspiration (d10)

Replaced Backstab with Bardic Inspiration
Replaced Second-Story Work with Ear of Deceit, Eye for Detail (Inquisitive subclass)
 
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I would go Bard 1, Rogue (Thief) 19 as the build. Musician origin feat (Entertainer Background). Friends and Prestidigitation as the cantrips and Command, Comprehend Languages, Detect Magic and Distort Value would be my spells - with them all explained as verbal trickery, knowledge, tomfoolery and magic items as to how they work if you want to avoid the idea of the PC being a spellcaster.
 

Let her earn it though play. When she finally gets to multiclass into bard, everyone will cheer a bit...
Personally, I'd allow a character to sort of..."backfill", if that makes sense? File this under "another optional rule that would be nice to have even if it usually wouldn't apply to me".

That is: She starts as a Rogue with the Entertainer background. She doesn't know magic. But she's really interested, taking Magic Initiate as her (customized) Origin feat. At 3rd level, instead of continuing Rogue (and thus picking a subclass for it), she takes a first level of Bard. Once she hits 3rd level Bard and has a subclass (I'd probably update the College of Eloquence for it), she can spend time "un-learning" her Rogue skills--focusing purely on her Bardic training. E.g. perhaps every other session, she can replace one Rogue level with the equivalent Bard level. That way, by the time she's (roughly) a 6th level character, she's got full Bard levels, despite not having "truly started" as a Bard originally.

Obviously this is more complicated than just saddling the character with those two Rogue levels, but I personally like the idea that someone grows out of their old skills and genuinely abandons them for something new.
 

I would post in a forgotten realms sub-forum, but I don't see one?

Olive Ruskettle is a Halfling in the Azure Bonds novels that came out in the 80s. In the Novels she is essentially a Bard, and says she is a Bard, but because only Humans, and Half-Elves could be Bards in 1E the novels go to great lengths to make it clear she is really a Thief with some Bard-like attributes.

If you read the novels what do you think? Bard, Rogue, multiclass Bard-Rogue, something else? What subclasses?

One of our groups is looking at playing an Azure Bonds adventure and I am thinking of doing an Olive Ruskettle knock off as my PC.
She is a straight rogue with entertainer background at most. Probably charlatan background fits even better.
 

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