Intelligent and ruthless criminal masterminds are some of the greatest antagonists to ever appear on film.

The following entries contain some spoilers for the movies discussed.

Every moment of his screen time dedicates to how cruel and unredeemable his character is.

The 10 Most Cold Blooded Criminal Masterminds in Movies, Ranked

Gyllenhaal does fantastic work portraying an antisocial criminal who is as mysterious as he is dangerous.

He stood out as the deadliest and most cunning criminal in a line-up of cold-blooded killers.

Valentine was an outwardly friendly, relatable man who tried to appear as a savior.

John Lithgow as Eric Qualen talking into a radio in the film Cliffhanger

Image via TriStar Pictures

He honestly believed his plan was the only way to help the planet.

Most fans ofGoodfellaswould agree thatJoe Pesci’s role as theunhinged mobster Tommy Devitowas the film’s standout antagonist.

However, it was De Niro’s character that was easily the biggest threat to the overall story.

Jake Gyllenhaal as Louis Bloom pointing at something off screen and smiling in Nightcrawler

Image via Open Road Films

Jimmy was more professional, reserved, and a seasoned career criminal.

However, his need to destroy his enemies overshadowed his compassion toward the ones he loved.

He becomes such an enjoyable antagonist that it becomes hard not to secretly root for his goals to succeed.

John Malkovich as Cyrus in Con Air (1997)

He didn’t just want to break the city through physical acts of violence.

KEEP READING:The 10 Smartest Movie Villains Of All Time, According To Letterboxd

Samuel L. Jackson as Richmond Valentine in Kingsman: The Secret Service

Image via 20th Century Fox

Rosamund Pike looking at the camera in Gone Girl

Image via 20th Century Studios

John Huston as Noah Cross in ‘Chinatown.'

Image via Paramount Pictures

Jimmy Conway (Robert De Niro) smokes a cigarette in Goodfellas

Image via Warner Bros.

Al Pacino in The-Godfather-Part-II

Image via Paramount Pictures

Alan Rickman as Hans Gruber in ‘Die Hard’ (1988)

Image via 20th Century Fox

Heath Ledger as The Joker in The Dark Knight

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