By Rachel Weingarten

Remember how shocking it was when we first encountered — and subsequently, all became mesmerized with — Don Draper, the charismatic anti-hero of Mad Men? If that wasn’t bad enough, many of us succumbed to the humor and charm of Negan, the barbed wire wrapped, bat-wielding leader of the Survivors in The Walking Dead.

From serial killer with a twisted heart of gold Dexter Morgan, to biker momma Gemma Teller Morrow on Sons of Anarchy, to a charming Lucifer’s new incarnation as a suave crime solver, why are these awful fictional characters so incredibly appealing? And more than that, is there anything we can actually learn from them?

Voldemort (Harry Potter): The Branding genius

Unlike Madonna and Beyonce, who still need their first names to identify them, Voldemort is so famous you don’t have to use his name for people to know exactly who you’re talking about. In J.K. Rowling’s Harry Potter series, “He Who Must Not Be Named” inspires so much fear, I’ve always thought that beyond all the evil, Voldemort’s brand is not really having one. In the work arena though, it’s probably a good idea to have people remember you both by name and by impressive deed. And not for being awful and ending the world and stuff.

Darth Vader (Star Wars): Don’t lead with fear

“Darth Vader is a terrible leader compared to some of the other generals in the Galactic Empire” said Dr. Tom Epperson, president of InnerWill Leadership Institute a national non-profit committed to transforming individuals and organizations through values-based leadership. “For example, in the early Star Wars films, other evil generals under Vader’s command are able to run the army and lead their forces. It seems like every time an evil plan is moving in the right direction, Vader comes in ruins everything.” Epperson explains that “fear ultimately inspires no loyalty from his people. Some of the other leaders in the empire, like those at the head of legions of Stormtroopers, are able to inspire loyalty; otherwise, they wouldn’t be able to keep a group of highly suspicious combative people together.”

Negan (The Walking Dead): The appreciator

Epperson points out, “In the Walking Dead, Negan actually values people. He sees people as resources that are crucial to his success. So while he inspires through intimidation, he generally wants to get the most out of people.” Epperson believes that while his methods are through intimidation, Negan wants people to use their strengths on the path to a future past the zombie apocalypse. “He wants to see people coming together in well-established roles. Yes, he’s an evil sociopath, yes he’s narcissistic, yes he’s out of his mind — but he fundamentally believes in people.”

The Wicked Witch of the West (Wizard of Oz): Stand up what’s yours

Henry DeVries, CEO (Chief Encouragement Officer) of Indie Books International LLC, and author of Persuade with a Story!, said, “Some people unfairly call this the ultimate chick flick — two women fighting over a pair of shoes. Unfair. Those slippers belonged to her sister, so the witch of the west was the rightful heir.” DeVries takeaway lesson? “Sometimes in your career you have to stand up for what is rightly yours.”

Hannibal Lecter (Silence of the Lambs): Learn how to barter

“Never work for free if people don’t appreciate it. Instead of just giving the FBI what they wanted, the good doctor was willing to bargain,” DeVries says. “Give and take is what win/win deals are all about. And if you are ever invited to the have dinner at the home of your boss, never underestimate the goodwill of bringing a good bottle of Chianti.”

Norman Bates (Psycho): Loyal to a fault

DeVries explains that Norman “was loyal to his dead mother, but he was still loyal. However, customer service at the Bates Motel left something to be desired.” A good lesson though, is even though you no longer work with someone, it’s good to try to do everything in your power to keep the relationship going.

Professor Moriarty (Sherlock Holmes): Go big or go home

DeVries says about Moriarty, “If you are going to commit, then commit whole-hog.” No one advises dedicating your life to the downfall of others, but if you do plan on doing something, allow yourself to think big.

Originally published at

Sign up to receive daily news, inspiration, and advice on how to master work and life from Ladders.