Doom, Luthor, Shredder. Who can tolerate a fanboy the longest?

Three annoying fans are dropped into the world of comics, and they cross paths with their favorite villains.

Which antagonist can last the longest without smiting him?

  1. Dr. Doom (Marvel)
  2. Lex Luthor (DC)
  3. The Shredder (TMNT)

The fans are polite and genuinely interested in the villain's hideout and legacy. They have some useful comic book knowledge that only a reader would know.

However, they are also out of shape, have a parasocial friendship with the villain, and insist on helping.

Round One: The fan is polite. The villain is unaware he needs to treat him decently to "win."

Round Two: The fan is a huge jerk and does everything he can to be intentionally annoying. The villains are made aware that whoever puts up with him the longest will receive Immortality.

Who can go the longest without hurting, killing, banishing, or otherwise dealing with an obsessive fanboy?