Heist fiction is not easy to write. It’s fast paced and twisty, and it takes a lot of characters.
Over the last two Wednesday posts, I’ve been throwing open the vault and letting out all crime writing secrets. If you need to catch up, you can get more help for your story with Tips for Writing a Heist and Picking the Loot. This week I’m talking about the characters.
Building any fictional heist crew starts with the same foundation as any other successful team: mutual self-interest and a certain level of professional courtesy. A bit of faith that the other team members know their jobs well enough not to get the rest of the group killed is a serious plus.
So here are 7 tips for creating a likeable gang of thieves.
1. Load up on leadership skills: The heist team is a basic pyramid structure. Someone needs to be at the top keeping everyone else in line. For me the path to creating a cheer-worthy heist crew started with a capable leader. I recommend packing this main character with all the attributes of a great boss. Make them smart, organized, and a good communicator. They should know how to delegate, how to take input from others, but be willing to make the difficult decisions.
2. Give the crew better than average looks and a lot of charisma: Who doesn’t love the idea of the sophisticated cat burglar? Having good-looking characters often plays into the story. You usually see it in the form of the decoy, or as the romantic subplot. The team needs to have enough charm to talk their way out of any sticky situation.
3. Shun the guns: This is critical for helping to create likeability. You don’t want the crew to engage in boundary crossing behaviors. No killing people. Make sure the crooks fight with their equals, or someone perceived as stronger. No picking on someone who is smaller and weaker. If the likeable crew gets aggressive, it’s after suitable provocation.
4. Show some emotion: A good heist boss shows he cares by engaging with the team, noticing their good work and helping them solve their problems. The team mirrors this affection back toward the leader in the form of respect, playful teasing and distress when something goes wrong.
5. Establish moral limits. Everyone needs a line they will not cross. Maybe your group only targets other bad guys. It’s hard to feel sorry for victims if they’re even bigger crooks than the heist team. The team can steal for a good cause. Or revenge can be the motive. What the crooks steal and why they steal it are two huge factors in creating sympathy for the heist team. 
6. Don’t skimp on humor: A touch of awkwardness, some goofy pranks, anything from fast one-liners to someone falling out of a chair, can create a few laughs and make the characters, even crooks, seem more friendly and approachable. It’s not mandatory the story drip with the funny stuff, but a heist needs some tension breaking moments.
7. Include negatives to overcome: The nature of an anti-hero is they evolve. Don’t forget to throw in a few negative behaviors for your characters to conquer. Maybe one of your team is always watching for signs of a double-cross, it makes them jumpy and short-tempered. Later you can reveal the secret of a past partner’s betrayal and show them lowering their guard and learning to trust again.
Since I’m prone to writing stories with lots of characters, I’ve written a few posts on building large character casts. If you haven’t written anything with 20 or more characters, you might find one of my other posts helpful: Assembly Required or The Do’s and Don’ts of Getting a Group Together.
Casting my characters was the only time I found watching films useful. That was when I learned heists and capers are surprisingly formulaic films. And they share a large number of trope characters. Have some fun, grab a stack of DVDs and a notebook. If you find a new way to make heist characters more likeable, please share your idea in the comments area.
I am enjoying these. Haven’t had much time to comment this week, but this is good stuff. Nice analysis of the genre going on here.
Does this: “Make them smart, organized, and a good communicator.” Sound like a blogger you know? LOL.
The bits about not picking on the weaker or getting aggressive without provocation are critical to the likeability factory.
And with rogues, charisma always helps, never hurts.
Hi Gene’O,
It was a crazy week for me too, so I know what you mean.
Yes, that does sound like someone I know, someone with world domination on his mind. You would have my vote for heist leader!
Writing about criminals is not easy, you have to find something to help readers relate.
I don’t think I’ve seen the Italian job but I liked Ocean’s 11 (and 12, I think I was burnt out by 13) and I agree with you and DL about Leverage. I miss that show.
The Heist post series has been fun and informative. Thanks.
Hi,
Leverage had a great mix of crimes, they did a lot of cons as well as some heists. Try to see at least one version of The Italian Job, I think you’ll like it.
The Italian Job is one of my favorite movies and the crew in it embodies everything you just wrote about. Another crew that I can think of is from television…LEVERAGE. So…so writing, but the make up of the crew was spot-on. 🙂
Thanks DL. I liked the second Italian Job better. The part with Minis is amazing in the second one, more comical in the first one. I also liked Leverage, they had nice cast chemistry with that show.