!!The Books
* CompleteMonster: Alex Cross has faced many revolting criminals, but these stand out as the worst:
** [[EvilFormerFriend Kyle Craig]], or [[DirtyCop The Mastermind]], is a former FBI special agent and Alex Cross's ArchEnemy. A violent individual since childhood, Kyle was responsible for multiple killings even before joining the FBI, including that of his own brother. As the Mastermind, Kyle perpetrates a series of bank robberies followed by murders in ''Roses Are Red'', making sure to dispose of his accomplices, and [[ILoveTheDead raping the women he had hired post-mortem]]. While his partners at the FBI are busy investigating the murderous robbers, Kyle rapes and kills a woman in a home invasion, and then sets his eyes on Alex's girlfriend, committing the same crime with her and mutilating the body afterwards. Kyle calls Alex to inform him about the horrendous death of his girlfriend, just so he could hear his reaction. Realizing in ''Violets Are Blue'' that he has been exposed, Kyle attempts to kill Alex's partner and later a woman he had saved from another killer, but is arrested and sent to death row. Assuming the identity of his attorney in ''Double Cross'', Kyle escapes and [[{{Matricide}} kills his mother]], using her money to travel around the world and murder more people, including the judge who had sentenced him to death. Failing to kill Alex, Kyle returns years later in ''Cross Fire'', this time posing as an FBI agent he had killed who had been assigned to work with Alex. Seeking to hurt Alex's loved ones, Kyle attempts to take his family hostage, and commits suicide upon defeat, dying in [[EvilCannotComprehendGood confusion to why Alex did not kill him]]. A merciless SerialKiller with an obsession for female bodies and being Alex's shadow, Kyle was one of the worst criminals Alex had to face in his career.
** [[PsychopathicManchild Gary Soneji]], real name Gary Murphy, is one of Alex Cross's earliest and most personal foes. First appearing in ''Along Came a Spider'', Soneji is a [[SerialKiller depraved killer]] who claims to have killed over 200 people and starts the book by brutally murdering two black families, mutilating the women and even [[WouldHurtAChild killing an infant]]. Longing to become the [[FameThroughInfamy most infamous criminal mastermind in modern history]], Soneji duplicates the Lindbergh baby case by abducting two private school children, fully intending on [[BuriedAlive burying them alive]] while he disappears without a trace. Killing the FBI agent in charge of the case as well as a schoolteacher, Soneji has a breakdown after his plan goes awry, and takes a [=McDonald's=] restaurant hostage, killing an innocent man and a cop. Upon his capture, Soneji quickly plans his escape, and once he's free he attempts to murder Alex Cross's family for revenge. Returning once again in ''Cat and Mouse'', Soneji, feeling he has [[DeathSeeker nothing to lose]] due to contracting AIDS in prison, decides that [[OmnicidalManiac the whole world]] deserves to be punished for his misfortunes, and goes on a cross-country killing spree, slaughtering innocent men, women, children, cops, and even his own wife; he leaves his young daughter [[CruelMercy alive]], but tied up in his house's cellar to slowly die of starvation. When confronted by Cross yet again, Soneji takes a bus full of innocent people hostage with a bomb and abducts a baby to ward off the cops before attempting to beat Cross to death for "ruining his life". A relentless and [[AxCrazy utterly unstable]] murderer who longs to top other killers in sheer brutality, Gary Soneji would stop at no limits to feed his pathological need for attention.
** Geoffrey Shafer, known by law enforcement as the Weasel, is one of Cross's most personal enemies. A diplomat moonlighting as a SerialKiller, Shafer is playing a "game" with a few other men that he met in [=MI6=], who style themselves after The Four HorsemenOfTheApocalypse, with Shafer playing the role of Death. He is introduced in ''Pop Goes the Weasel'', when he finds a prostitute and brutally kills her. He then puts on {{blackface}}, goes out in a cab, picks up a woman and murders her. He later goes out again, finds a man, and kills him too. Shafer stalks George Bayer, who plays Famine in the "game", murders the women he solicited, and leaves the bodies in a compromising position. Realizing the police are on to him he goes south to Maryland and kills a mother and her teenage daughter. Shafer then targets DC Detective and Cross's love interest Patsy Hampton and brutally kills her. Cross arrests him, but evidence being inadmissible due to [[DiplomaticImpunity diplomatic immunity]] means he gets acquitted. Shafer then kidnaps Cross's fiancée Christine. He murders the other players of the "game". After a fight with Cross he apparently dies, but resurfaces in Europe and kills his wife. He reappears in ''London Bridges'' living in Brazil. Here he continues his murderous hobbies until The Wolf uses a streetwalker to draw him out, kidnap him, and get Shafer to work for him. Shafer bombs an army base, then meets a sniper and has her kill the CIA Director. He later goes out and kills another prostitute. After that he goes and confronts his sister-in-law and children. He threatens them, asks them for a kiss, and when they refuse he only refrains from killing them because he states that he "does not have permission" to kill them.
** ''Cross Country'': [[TheBrute Abidemi "The Tiger" Sowande]] is a nihilistic African [[WarForFunAndProfit warlord]] driven by his own amoral belief in committing atrocities ForTheEvulz. The leader of a large group of savage ChildSoldiers, and an [[PsychoForHire attack dog]] for corrupt members of the CIA, Tiger grabs Alex's attention by dismembering his ex-girlfriend and her entire family, [[WouldHurtAChild children included]]. Having perpetrated countless gut-wrenching crimes with his minions, Tiger rapes and murders Alex's friend in front of him, but not before massacring her entire family for fun.
* DracoInLeatherPants: Some interpretations of the Mastermind.
* FirstInstallmentWins: ''Along Came a Spider'' is often universally agreed to be the best of the Alex Cross novels.
* HarsherInHindsight: Kevin Olmstead in ''Cross My Heart'' targeting [[HappyEndingMassage massage parlors]] is disturbingly reminiscent of the 2021 Atlanta shootings.
* MoralEventHorizon:
** Geoffrey Shafer starts out as somewhat likable in an evil way until a certain point, but crosses the line with [[spoiler:the murder of Patsy Hampton]].
** Ron Guidice crosses it by framing Alex for drug use, which leads directly to [[spoiler:Ava's death]]. And that's ''before'' the InternalReveal that [[spoiler:he had disguised himself as her boyfriend]], thanks to [[spoiler:her]] roommate at the foster home.
* {{Squick}}:
** ''Kiss the Girls''. One scene in particular involves Casanova using warm milk to lead a live snake into the rectum of one of his victims. Many reviews cite this scene as so disturbing it ruins the entire novel. [[note]]Snakes don't actually drink milk. Blame Creator/ArthurConanDoyle for this one.[[/note]]
** The lovingly detailed description of The Mastermind having sex with a corpse in ''Roses Are Red''.
** ''Four Blind Mice'' has three contract killers (hence the title), and one of them is described as getting hard at the memory of murder.
** ''I, Alex Cross'' has Zeus, who possibly tops Casanova in terms of being a disgusting murderous sex fiend.

!!The Movie
* CompleteMonster: The sadistic "[[OnlyKnownByTheirNickname Picasso]]" is an assassin who was [[PsychoForHire hired to eliminate]] Giles Mercier and his associates Fan Yau Lee and Erich Nunemacher. After being invited to Fan Yau's house, he proceeds to sedate her with a paralyzing drug. Afterwards, he murders all of her bodyguards and tortures her to death by [[{{Fingore}} cutting off all of her fingers]]. He later goes after Nunemacher, but fails to kill him due to Alex Cross and his partners Monica and Tommy interfering. As punishment for their interference, Picasso breaks into Monica's apartment and tortures her to death, shortly before [[TargetedToHurtTheHero sending a photo of her body to Cross's cellphone]]. Picasso then [[ItsPersonal makes it personal]] by murdering [[spoiler:Maria, Cross's pregnant wife]], and later calls him after her funeral, telling Cross that the only reason why he killed her instead of him was so he could make him suffer. Picasso then goes after Giles Mercier, attacking his convoy with a rocket and killing several police officers, along with Nunemacher and Mercier[[spoiler:'s double]]. During Picasso's final confrontation with Cross, Picasso subdues Cross and attempts to inject him with the same paralyzing drug as well.
** Casanova can be found at YMMV/KissTheGirls.
* HarsherInHindsight: Tommy jokes shortly after finding Fan Yau's safe that he'd want Cross to be wrong at least once. What are Cross' first words to Tommy after [[spoiler:his wife is killed]]?
--> '''Alex Cross''': ''(tearfully)'' "I got it wrong, man..."
* SugarWiki/HeReallyCanAct:
** Matthew Fox shows some real impressive acting chops as Picasso.
** Likewise, Creator/TylerPerry is pretty impressive in the dramatic moments.
* {{Narm}}: The tagline "Don't Cross Alex Cross" is a rather laughable use of the character's name.
* NauseaFuel: Picasso's first victim had all her fingers cut off and she could feel it all without reacting.
* OneSceneWonder: Creator/GiancarloEsposito's (''Series/BreakingBad'' and ''Series/{{Revolution}}'') quick scene as Daramus Holiday, [[spoiler: the uncle of a teenager about to be convicted for murder]].
* QuestionableCasting: Many people raised an eye brow when it was announced that Creator/TylerPerry would be playing Alex Cross, though some critics did praise his acting.
* SignatureScene: The final fight between Cross and Picasso, which is a showcase of some of the tropes that plague modern Hollywood action movies: excessive {{shakycam}} and closeups to hide poor fight choreography, OrangeBlueContrast, and [[SpecialEffectFailure obvious usage]] of CGI and ChromaKey.
* {{Squick}}: Alex using the first victim's severed thumb to open her safe.
* TearJerker: [[spoiler: Alex's wife getting killed by Picasso and especially the scene where he tries to comfort his daughter over her mother's death, relating it to his own father's death, which makes it even sadder]].
* TheyWastedAPerfectlyGoodCharacter: Some viewers were upset that [[spoiler:Monica Ashe was killed off [[ForgottenFallenFriend and then forgotten about]]]], mostly since she was the film's only ActionGirl who was portrayed by a relatively good actress and had an ongoing subplot with Tommy.
-------