I find the most interesting crime fiction to be stories wherein the protagonist must make a deal with a morally ambiguous and seemingly villainous character. And that villainous ally? They usually have their own strange moral code and want something in return. At least one of them usually ends up changed for the worse, and it would be apt to recall that a good compromise makes both sides unhappy. Here are examples of these slippery relationships in nine well-known books.

The Godfather, by Mario Puzo

Everyone knows this story. Michael is the son of Don Corleone, destined for a good education and a legitimate career. He has tried his whole life to stay clear of the Mafia. But Michael is driven by something deeper than his personal ethics—a fealty to his family. Rivals want Don Corleone to go against his principles and join them in the drug trade. When he refuses they try to kill him. In response to the attempted assassination of his father, Michael’s ancient sense of honor and loyalty kick in. He allies with his father’s henchmen in order to avenge and protect his family. Don Corleone, the father, sadly watches his son’s descent as if he knew all along that it was inevitable. In this novel, tradition and family force Michael to ally with the morally ambiguous part of his family—a compromise that robs him of the ability to love.

Winter’s Bone, by Daniel Woodrell

Family loyalty and history are also huge determinants in the work of Daniel Woodrell, who writes wonderful descriptions of the winter landscape in a third-person voice thick with the Ozarks. In Winter’s Bone, Ree Dolly is sixteen. She must protect and care for her mentally ill mother and her two young brothers. Her one hope is to someday be free enough that she can join the army. As the story opens, her father, a meth cooker, has jumped bail and disappeared. A deputy marshall shows up and informs the family that their father put up the house and their timber acres as collateral for the bail bond. If Ree doesn’t make her father show up in court the next week, she, her mother, and her two brothers will lose the little that they own.

Ree must align with the murderers and drug dealers her father worked with in order to find him and save her family. As with Michael Corleone, it is as if a whole society is pulling her back into what she is trying to escape. Through force of will, she manages to convince the criminals around her to rise above their deadened selves and help, perhaps to prove to themselves they are still capable of compassion. This story is a devastating portrait of a society crushed by inescapable drugs and poverty, where violence hides tenderness, and where loyalty to family is everything.

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The Girl With The Dragon Tattoo, by Stieg Larsson

Larsson’s famous work features two morally slippery protagonists. Mikael Blomkvist is a crusading journalist convicted of slander. His career revolves around ferreting out government and corporate corruption. He has no sympathy for those he hunts, nor for the friends and family who suffer because of his dogged determination to do what he thinks is right. Lizbeth Salander has a similar determination to go her own way and to mercilessly punish those who’ve wronged her.

Devil in a Blue Dress, by Walter Mosley

In Mosley’s crime novel, friendship carries a loyalty as deep as family—and just as dangerous. Easy Rawlins is an out-of-work black man in L.A. who has just returned from World War II. He needs money and accepts a job to find a young white woman who hangs out with black men, the titular “devil in the blue dress.” The world Easy must negotiate is full of violence and racism. In order to survive and find her, Easy needs his childhood best friend Mouse, a killer driven to do almost anything for money. Easy fears the kind of violence that Mouse might make him a part of. But even knowing this, Easy accepts Mouse’s help. Easy needs Mouse to do the killing so that Easy can hang onto his own sense of goodness.

The Gold Coast, by Nelson DeMille

In this novel, we view a wealthy world of moral ambiguity. John Sutter is a cynical, old-money Wall Street lawyer who is bored with his life on the North Shore of Long Island. He and his snooty wife, Susan, keep their marriage vibrant with role-play sex games. Then Frank Bellarosa, a charming Mafia don, moves in next door. Sutter and Susan are drawn to Bellarosa’s out-of-bounds excitement. Bellarosa needs Sutter because of his landed place in the community and because he wants Sutter to do some upper-crust legal wrangling. It is Gatsby meets the Godfather.

There is more than legal and social jeopardy at risk here. Despite Sutter’s Ivy League law education and refined self-righteousness, he is blind to himself. Reading this book, I often found myself laughing out loud at his sardonic observations and the petty meanness his upbringing makes him feel entitled to. In the end, which morally ambiguous character is seduced by whom?

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The Silence of the Lambs, by Thomas Harris

Clarice Starling, like Red Dolly, is trying to escape her past. She is new to the FBI and her boss offers her an assignment that ambitious Clarice is determined to ace. She must get information from uncooperative Hannibal Lecter, a notorious serial killer. If Starling succeeds in inducing Lecter to use his insights to help find a notorious killer, she will rise in the FBI hierarchy and in the eyes of her boss. Lecter sees Starling as a chance to exchange information for a federal prison cell with books and a window overlooking a woods. But Lecter is driven by curiosity. He senses that Starling’s ambition is caused by her poor upbringing and some terrible secret. Now he will only trade what he knows if she reveals what happened in her childhood. We expect Lecter to use this intimate knowledge to destroy Starling. But he doesn’t. The serial killer is actually a good therapist.

Give me Your Hand, by Megan Abbott

Kit wants to escape her past for a different reason than Clarice Starling. Her best friend in high school, Diane, spurred her to academic achievement. But Diane also committed a terrible crime. When she confessed to Kit, Kit shunned her but never went to the police. Kit has felt complicit ever since.

The story is told in flashbacks and present time. In the present, Kit works in a prestigious research lab and is shocked when Diane joins the same lab. A terrible accident occurs and Kit may be held criminally responsible. She needs Diane’s help to cover it up and save her career. Diane hopes that Kit will now forgive her. But Kit’s compromise leads to more lies. She is becoming like Diane, inexorably edging toward worse things. Both the past and the present crimes tie them together.

This novel poses a contemporary question: What sacrifice will very ambitious women make for their careers? Long a male question, this is now firmly one for female characters, as well. The three principal women in the novel—Kit, Diane, and Dr. Severin, the professor in charge of the lab—have all chosen their careers over their romantic relationships. As people die, Kit feels guilty and bereft. At the same time, she can’t help feeling proud of being in this prestigious lab that’s doing groundbreaking research. She basks in the glow of Dr. Severin’s compliments and feels her future unfurling. Ambition is as much a morally ambiguous ally as Diane.

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Stranger in Paradise, by Robert B. Parker

Sometimes a strong character, fully cognizant of the risks, can ally with a villain and maintain his core values. Parker’s chief of police, Jesse Stone, is uneasy about the arrival of Wilson Crow Cromartie. Crow is an Apache hit man, who has returned to Paradise ten years after escaping in a hail of blood and bullets with ten million dollars. Crow wants Stone to stay out of his way as he searches out the fourteen-year-old daughter of a Miami gangster. Crow has been paid to force the girl to return home to her father. But when Crow is ordered to kill the girl’s mother, he abandons the job and turns against the man who hired him. He likes women and doesn’t kill them. Stone sees an idealized Apache warrior code in Crow. He and Crow both want to help the teenage girl. For that, Stone is willing to skirt the law. As for the girl, she’s a brat. But Stone and Crow are following higher principles that will leave them both mostly unchanged. As usual, Parker’s dialogue crackles.

Strangers on a Train, by Patricia Highsmith

No one emerges unscathed in this classic crime story. Guy is a successful architect with a cheating wife he can’t divorce. He meets Bruno on a train. Bruno has a suggestion for a perfect murder. Bruno will kill Guy’s wife if Guy will kill Bruno’s father. Because they have never met before, no one will suspect. Guy doesn’t really think that Bruno will follow through, but part of him wants it to happen. This internal compromise is the moral center of the story. In his mind, Guy has traded his conscience for the elimination of his evil wife. When Bruno fulfills his part of the bargain, Guy doesn’t go to the police, which makes him more complicit. He also doesn’t tell his new wife, which threatens to extinguish the most sacred thing in his life, his marriage. Bruno, on the other hand, is obsessed and full of repressed love for Guy. He threatens to expose Guy for his part in the murder unless Guy kills Bruno’s father. Guy finds himself compelled to do what Bruno wants.

For Highsmith, Bruno isn’t so much a villain but a dark part of Guy himself. Guy must ally with the evil hiding inside his personality to get what he wants. That part of him, in turn, wants to consume him. Which will win out—the lying side that will prolong his marriage and make him miserable, or the higher side that will demand he sacrifice everything to atone for what he has done?