In 5e: Simon the Devious and the Leather Skins (from What We Do In The Shadows) as a Dhampir Hexblade Warlock with Pact of the Chain.
Between the chain familiar (Count Rapula), a zombie from Undying Servitude (Ken the Accountant), Summon Undead (Blagvlad the Exsanguinator, or Desdemona the Shrieker, or Impussa) and an Accursed Specter (Carol), you have a 4-person posse by level 6. It grows situationally or permanently when you gain access to Danse Macabre, Create Undead, and Finger of Death.
Mechanically, you’re done by 13, and can either finish off with Bard (probably Whispers) or Paladin (Oathbreaker). Either way, take Inspiring Leader once you’ve maxed Cha, and then go get yourself that cursed witch’s hat!
Something about English wants me to say it should be “Battle of the Santas Clause,” but not knowing any of the rules, I couldn’t tell you why.