Each character is right after their first movies. Any character from TV is from their latest appearance on TV.

The Reaping:

District 1:

Emilio Largo

James Bond

District 2:

Captain Davy Jones

Captain Jack Sparrow

District 3:

Sauron

Aragorn Strider, son of Arathorn

District 4:

Krall

Captain James T. Kirk

District 5:

Moriarty

Sherlock

District 6:

The Master

The 12th Doctor

District 7:

Red Skull

Steve Rogers

District 8:

Lord Voldemort, He who shall not be named.

Harry Potter

District 9:

The Joker

Bruce Wayne

District 10:

Rene Belloq

Henry Jones Jr.

District 11:

Darth Vader, Anakin Skywalker

Luke Skywalker

District 12:

Coriolanus Snow

Katniss Everdeen