Top 10 Double-Crossing Movie Mentors

It’s a classic dynamic: the veteran cop, unafraid of bending the rules, is paired with a by-the-book rookie. But in the end, the newbie comes to respect the bigger picture - the pursuit of justice. Well... there’s nothing just about Alonzo Harris. He claims to be teaching rookie Jake Hoyt how to survive police work in South Central L.A., but every lesson, from smoking marijuana to stealing drug money, serves one crooked purpose – to see that Alonzo’s debt to the Russian Mob is paid. When Jake refuses to play along, Alonzo arranges to have him killed – talk about setting a bad example.

Who can deny Al Pacino when he turns on the charm? In this flick, Pacino takes on the role of the most compelling smooth talker there is - Satan himself. Keanu Reeves plays Kevin Lomax, a lawyer who catches The Devil’s eye following his successful defense of a child molester. His boss, John Milton, is everything you could hope for in a mentor - charming, witty, smart, supportive and inspiring. If only he weren’t literally the Devil, slowly corrupting Kevin using his classic recipe of temptation and freewill. Satan’s end goal? Getting his new protégé to conceive the antichrist with his own half-sister. Long hours is one thing… but that’s asking too much of any employee.

It’s always nice to be able to measure things on the “Morgan Freeman spectrum”. On the “mentor” scale, Freeman’s Detective Somerset is about as perfectly balanced a mentor as you could ask for. On the bottom end of that scale… is Sloan. If there’s one person you’d think you could trust, it would be the head of an organization of assassins that uses a magic “Loom of Fate” to dictate who they kill for the betterment of the world. You’d expect the organization to really vet a person before making them the leader. But nothing corrupts quite like self-preservation, and when the loom instructs Sloan to have Fraternity members killed, himself included, he starts faking results for profit.

It hurts to think of what that galaxy far far away might’ve looked like had Anakin never been assigned to protect Palpatine. While fans can certainly find flaws with the prequel trilogy, Senator-then-Chancellor Palpatine makes for a convincingly duplicitous and masterful Sith Lord. Pretending to have the best interest of the Republic in mind and feigning concern for the wellbeing of those around him, emotional manipulation is truly his greatest strength. His ultimate prize is Anakin, and the manner in which he pulled him over to the dark side by exploiting those closest to him is definitely worthy of high-praise.

Following the death of Tony Stark’s parents, Obadiah Stane, Howard Stark’s partner, helps Tony transition into adulthood and his new role at Stark Industries. It’s always painful to see a mentor become an enemy, even more so when that person is a father figure. So when Tony discovers that his company has secretly been selling weapons on the black market to terrorist groups, he never suspects the man he’s come to love like family. But Stane is revealed to have done a lot more than sell illegal weapons; he also arranged to have Tony killed, and when that failed, he attempted to kill Tony himself in order to steal the Iron Man tech.

As the white wizard, Saruman should’ve known better than to mess with dark magical artifacts. For the very same reason that Gandalf refuses to wield the ring, Saruman succumbs to Sauron’s offering. As the leader of the Council of Wizards, he is considered to be one of the wisest, most respected and trusted figures in all of Middle-Earth, so we can forgive Gandalf for not seeing through his deception. Thankfully Saruman doesn’t finish the job of killing Gandalf, and the Grey Wizard has a chance to learn from his mistakes. Grima Wormtongue, advisor to King Theoden, on the other hand, is about the slimiest, most no-good advisor you could ask for – but at least he wears his treachery on his sleeve.

Purpose; it’s something everyone is searching for in life, including Elijah Price, comic book curator and Type 1 osteogenesis imperfecta sufferer. Elijah’s physical limitations make him identify with the villains in comic books, and this leads him to find his purpose: he was born to be a villain. But what is a super villain without a superhero? Enter David Dunn, a man impervious to harm. Elijah encourages David to become the hero he’s meant to be, and despite some initial trepidation, David eventually follows his new friend’s advice. Elijah hasn’t just met his match; he’s actively created him, crafting a foe out of a friend. What David understands as encouragement is actually Elijah’s attempt to turn him into his personal nemesis.

Who is more trusting of others than children? For kids in the ‘90s at least, it seems safe to assume that Jafar probably taught them their first lesson in betrayal. He is so transparently evil, that only someone so blissfully unaware and naive as the Sultan could have not seen it coming. Come to think of it… the Sultan kind of acts like a child, so maybe Jafar was his first lesson in deception too. Jafar is the definition of “conniving”, “evil” and “slimy” - all wrapped in one. He’ll stop at nothing to wrestle control of Agrabah from the poor Sultan, who sadly, never sees the betrayal coming.

Power is rarely held by those who prioritize the wellbeing of others. It’s a simple truth that Bud Fox, played by Charlie Sheen, probably wishes he’d known before he got involved with legendary Wall Street figure Gordon Gekko. Blinded by ambition and in awe of his business idol, Fox will do anything Gekko asks, regardless of legality. Too late, Fox sees Gekko for what he is - a ruthless corporate raider. Gekko intends to manipulate a deal brought to him by Fox, ultimately leaving Fox’s own father and every employee at his company out of a job.

Before we unveil our top pick, here are a few honorable mentions.
- Capt. Dudley Smith
“L.A. Confidential” (1997)

- Professor Robert Callaghan
“Big Hero 6” (2014)

- Capt. Joseph Korso
“Titan A.E.” (2000)

- Avery Tolar
“The Firm” (1993)

- President Alma Coin
“The Hunger Games: Mockingjay - Part 2” (2015)

Ducard took an angry young Bruce Wayne and gave him the tools to avenge the death of his parents, starting him on his journey to becoming Batman. But when put to the final test, Bruce refuses to adopt Ducard’s harsh version of justice, opting rather to destroy the temple and return to Gotham. But Ducard is not simply the advisor to Ra’s Al Ghul – he is (and always had been) the true leader of the League of Shadows; the real Ra’s Al Ghul. The assassins come to Gotham to complete their cleansing mission, pitting pupil against mentor in the process. And we’re sure Bruce Wayne would tell you: nothing stings quite like finding out your mentor wants to destroy you and the city you’ve vowed to protect.

Do you agree with our list? What treacherous mentor or advisor do you most love to hate? For more sneaky top 10s published every day, be sure to subscribe to WatchMojo.com.