Best 'master of disguise'

[Naanomi]

A concept I've always liked is a 'pretends to be a bad guy' master of disguise type character. 5e offers several paths for this... What do people think is the best?

Class:
Rogue: Mastermind
-pros: General skills strong, unique 'lying' abilities to counter BBEG abilities to shutdown schtick
-cons: somewhat weak archetype overall

Rogue: Assassin
-pros: unique disguise based abilities for authentic false persona; strong combat abilities, general skills strong
-cons: not charisma based, abilities slow to use and many GMs would let anyone use some variation of them

Bard: Lore
-pros: all the right spells, boost skills and reduce opponant's insight, charisma based, big list of skills
-cons: less combat capable in general

Warlock: (varies)
-pros: several 'social' spells; invisible, socially capable familiar to 'help' or book with guidance; unlimited disguise self, charisma based, good combat option needing little investment
-cons: little/no class abilities directly boosting disguise schtick


Races:
-half-elf: big stat boosts in all the right places, bonus skills and languages, could pass for human or one of many types of elves with disguise

-Variant human: peaceable stats, bonus skill and language, start with Actor feat

-lightfoot halfling: good stat boosts, potential small disguises (fey, human child, goblin)

-Tiefling: bad choice overall, but potential to pretend to be a true demon/devil

[Regitnui]

Changeling. Free at-will alter self.

[Biggstick]

Warlocks have access to an invocation that let's them cast disguise self at will...

[Naanomi]

Changeling. Free at-will alter self.
Well yeah, if UA material is allowed it is an (if not the) obvious choice

[Corran]

A concept I've always liked is a 'pretends to be a bad guy' master of disguise type character.

Not sure exactly what you mean by that, but here are my thoughts on disguise techniques.

Alter self seems to be the best option, as it takes care of everything, from your physical appearance holding up to inspection, to even the sound of the voice. One problem is that it takes up concentration, though that wont be an issue most of the time, as you are probably going to use it out of combat. The bigger issue is that it consumes a 2nd level spell slot and that it can go through your spell slots very quickly if you are planning on spamming it for one reason or another.

For no resource expenditure, mask of many faces combined with the actor feat will let you spam disguises as often and as much as you want. Pair that with a very good deception skill, and with a good roleplaying, so that your enemies will rarely get the opportunity to roll to see through your disguise.

Personally I prefer the alter self version, as it guarantees success and does not require feat investment.

It also strikes me as a very odd thing that disguise/alter self, deception, and proficiency with the disguise kit, dont have any ind of synergy. Odd.....

[ThatKreacher]

I just made a master of disguise right now of sorts, more a spy. half elf wizard(enchantress or illusion)15/warlock2/thief3. invocations, cunning action, eldritch blast, lots of spells, and lots of good fluff I'm working with.

[Caskwell]

It also strikes me as a very odd thing that disguise/alter self, deception, and proficiency with the disguise kit, dont have any ind of synergy. Odd.....

But Alter Self and Disguise Self do have synergy!. Basically you can Alter Self into the right shape for the disguise and use (1hr duration, no Concentration) Disguise Self to lay as skin tight as possible to complete the disguise with clothing, proper insignia, etc. Assuming you don't try anything too flashy with Disguise Self and don't have any easily detectable elements (i.e. hat that's not there), there's really no reason for anyone to doubt the illusion. Of course, this angle could be covered by stealing uniforms or buying expensive court clothes, but that's not always an option.

[Caskwell]

My vote for best of what you listed would be Lore Bard. As you pointed out, everything is there except high combat effectiveness. But given that this archetype would be trying to avoid combat by befriending or distracting the bad guy, pure combat effectiveness is beside the point - you'd just want to be sure to have sneaky buddy/party ready to strike once you gain the bad guys confidence. And once they do, the Lore Bard is pretty good at support and control (vs low Wis saves at least).

[JumboWheat01]

Forget the rest of these. There's one clear master of disguise for hiding under evil's nose and pretending to be one of them.

Step One: Be a Moon Druid
Step Two: Turn into a cat
Step Three: Curl up in the boss's lap
Step Four: Learn all of the boss's secrets
Step Five: Turn into a dinosaur and eat the boss

...Maybe skip the last part if you wanna keep your cover.

[Regitnui]

Forget the rest of these. There's one clear master of disguise for hiding under evil's nose and pretending to be one of them.

Step One: Be a Moon Druid
Step Two: Turn into a cat
Step Three: Curl up in the boss's lap
Step Four: Learn all of the boss's secrets
Step Five: Turn into a dinosaur and eat the boss

...Maybe skip the last part if you wanna keep your cover.

You've won this thread. Close it, nobody can make this better.

[Corran]

Forget the rest of these. There's one clear master of disguise for hiding under evil's nose and pretending to be one of them.

Step One: Be a Moon Druid
Step Two: Turn into a cat
Step Three: Curl up in the boss's lap
Step Four: Learn all of the boss's secrets
Step Five: Turn into a dinosaur and eat the boss

...Maybe skip the last part if you wanna keep your cover.
'' ..........you failed to carry out my orders, and that makes me angry. And when I get angry, Mr Bigglesworth gets upset (cat on the lap of BBEV goes meow as he pets it). And when Mr Bigglesworth gets upset, PEOPLE DIE!!!!!!!''
-part of the BBEG's top meeting with his advisors and mooks (stolen from Austin Powers).

Obviously the cat is privy to all the BBEG's plans, because in all honestly, every decent BBEG will not resist the temptation of keeping that white fur fluffy stray cat that he accidentally came accross one day.

Thread won by JumboWheat01, I concur.