help me make a magical con man

[Joe dirt]

i was thinking of going sorcerer for charisma based casting, human with actor feat for successful disguise self+charm person trickery, and charlatan background

any suggestions?

[Sepok]

Bard and Warlock make a very good combo for a conman.

- Bard for Performance and Deception Expertise.
- Warlock for the at-will Disguise Self.

Go Great Old One warlock for the telepathy and you can really get inside your mark's head. You can't read minds, but just whispering in their head to them to throw them off balance. Add in the Minor Illusion cantrip and you can play a bogus exorcist/ghost-buster.

EDIT: Use HEX to give them disadvantage on WIS skills. They will never make an Insight roll vs your CHA skills.

[JumboWheat01]

Arcane Trickster is pretty much designed to be a magical con-man. A focus on Enchantment and Illusion schools, all the rogue goodies on top of that, and whatever criminal-based background you want.

[Ruslan]

Lore Bard. Expertise in Deception, and Cutting Words to reduce your mark's Insight check. Grab Guidance somehow (with Magical Secrets or Magic Initiate).

[Degwerks]

Both Arcane Trickster & Bard make great con men with Charlatan. I'd add 2-3 levels of Warlock though.

With Disguise Self at will invocation and friends cantrip you'll be living large as a conman. Adding in a class with double prof bonus in deception or persuasion is icing on the cake.

I'd go with a 1/2 elf Bard 3/Warlock 2. Taking the Disguise Self & Invisibility invocations. Friends cantrip too. I'd find myself a choice Mark to con, then Disguise myself as the "mark", then go find the constable/sheriff guy and cast Friends on the sheriff. Leave in a hurry, rush to the "mark", disguise myself differently, con him out of something using Friends maybe, and leave. When he tries to report you to the sheriff, the sheriff will already be hostile towards the Mark due to earlier use of Friends. Then use your amazing deception/persuasion skill at double prof to convince sheriff of innocence and say the Mark is the liar.

Edit: go lore bard 3+/warlock tome pact 3. Grab Guidance cantrip & use Hex & Cutting Words on difficult marks.

[Iguanodon]

Lore Bard 3 for cutting words, Divination Wizard 2 for portent. With these tools at your arsenal, no one will be able to get the ring on the peg or pick the right bowl.

Also, take the lucky feat if you can get it. Your goal should be to make your victims trick themselves into wasting more money, since they believe they can do it! I don't really like illusions for this, since a lucky save is all they need. Go for the fate-manipulation-type stuff.