Making the shadiest character?

[Trey Bright]

So thinking of setting up a shadow sorcerer and I'm wondering if a 3 or 4 dip in to Gloom:Ranger would be a good idea? Also, just for the sake of sake, I'm planning on the dark elf variant of the half elf to get a little extra magic.
Also, is there any reason that the dark elf variant of the half elf wouldn't qualify for the half elf magic feat?

EDIT:
Okay, so a gloomstalker/shadow monk would probably be a good Multiclass
Hexblade/Shadowsorcerer would also be good
both would be fairly shady, yeah? What levels would y'all recommend? Which should be the dominant number and home many levels ya think?
I was thinking Hexblade:Blade4/Sorcerer:Shadow16 for the proficiencies so you start with hexblade?
Monk is just such a good class, I'm not sure I'd want to multiclass out of it...

[Ventruenox]

If you are playing AL, then you would be violating the PHB+1 rule. Half-Elf variants are from SCAG; the other options are from Xanathar's. Other than that, a Half-Drow is eligible for the Elven Accuracy feat, but not the Drow High Magic feat. As always, ask your DM. I would probably allow it.

I am curious about your multiclassing choices. Are you rolling your stats? The build you are describing is quite MAD (CHA, DEX, WIS all over 13). I am assuming that you want Gloom Stalker for the invisibility to darkvision? Darkvision can't see through the Sorc's magical Darkness, so that's quite a dip for a somewhat redundant ability.

Warlock, Bard, or Paladin have better synergy with your Shadow Sorc. If you multiclass Hexblade-lock, then you will be SAD, & get weapon/armor proficiencies to Gish if you so desire.

If you tell us a bit more about your campaign and party composition, we may be able to steer you in a better direction.

[Waffle_Iron]

If playing a home game, and not AL, a dark elf, gloom stalker, shadow monk is a pretty shady combo. Ranger 3/ monk 17 gives you enough ki to do the fun monk stuff, and just enough ranger to go well with it.

[opaopajr]

A Skulker (feat) Actor (feat) whispering snark from the dark. Castin' shade all day!

[QuickLyRaiNbow]

A Skulker (feat) Actor (feat) whispering snark from the dark. Castin' shade all day!

Make it a Bard so your snark can be vicious mockery and cutting words.

[Trey Bright]

If you are playing AL, then you would be violating the PHB+1 rule. Half-Elf variants are from SCAG; the other options are from Xanathar's. Other than that, a Half-Drow is eligible for the Elven Accuracy feat, but not the Drow High Magic feat. As always, ask your DM. I would probably allow it.

I am curious about your multiclassing choices. Are you rolling your stats? The build you are describing is quite MAD (CHA, DEX, WIS all over 13). I am assuming that you want Gloom Stalker for the invisibility to darkvision? Darkvision can't see through the Sorc's magical Darkness, so that's quite a dip for a somewhat redundant ability.

Warlock, Bard, or Paladin have better synergy with your Shadow Sorc. If you multiclass Hexblade-lock, then you will be SAD, & get weapon/armor proficiencies to Gish if you so desire.

If you tell us a bit more about your campaign and party composition, we may be able to steer you in a better direction.

Right now this is mostly brainstorming character builds for a homebrew game. I'm going to be running my first game as a dm this summer with some friends who have experience with 3.5, but not 5e. I've played quite a bit of 5e and have all the books (not the modules, just the player/dm books) and I'm thinking about concepts that I my players are interested in, or if they aren't picked up, that could make interesting NPC's.

I suppose if I were playing gloom-shadow, I'd need to start as a ranger for the proficiencies, then just choose stats that would allow me to immidately mc in to SS.

[mgshamster]

You need to slip in a shadow monk in there somewhere. :)

[Grod_The_Giant]

Probably not, no. Ranger, even with a subclass as good as Gloom Stalker, doesn't give you anything that's worth the loss of so much casting progression. I mean, not much is, but you're not getting even the synergy of Paladin or Warlock.

[Caelic]

Shadow Sorcerer and Hexblade have great thematic synergy, since both draw their power from the Shadowfell.

[Sigreid]

For the shadiest character see if your DM will let you home brew a treent.

Sorry. Had to be done. I'll be quiet now.

[Dalebert]

Thematically they seem to fit like a glove. Mechanically, not so much because...

Darkvision can't see through the Sorc's magical Darkness, so that's quite a dip for a somewhat redundant ability.

This. Magical Darkness for just 2 sorc points that let's you see through it will almost always trump the Gloomstalker ability. You're dependent on natural darkness. It's very nice--don't get me wrong--and will be useful. It's just being able to create darkness that only you (generally) can see through as needed is generally better. I also think that Gloomstalker ability is going to not work nearly as much at higher levels when there are more things with blindsight, Devil's Sight, True Sight, etc.

Probably not, no. Ranger, even with a subclass as good as Gloom Stalker, doesn't give you anything that's worth the loss of so much casting progression. I mean, not much is, but you're not getting even the synergy of Paladin or Warlock.

Tend to agree, especially for the reason given above, i.e. because you already have darkness that conceals you. If you do it, I would say make a sort of melee sorc build so that it has more synergy.

[Trey Bright]

Shadow Sorcerer and Hexblade have great thematic synergy, since both draw their power from the Shadowfell.

For the shadiest character see if your DM will let you home brew a treent.

Sorry. Had to be done. I'll be quiet now.

lol Someone on reddit recommeded the exact same thing.