The 10 Most Shocking Movie Castings of All Time

5. Adam Sandler – Punch-Drunk Love (2002)


It’s easy to criticize typical Adam Sandler comedies, and by default it become easy to dismiss the actor who consistently appears in them. Not that appearing in an average movie means an actor can’t do anything better – John Turturro shows up in Sandler’s movies, and he’s certainly proven his abilities; but Sandler hadn’t given audiences much better material to judge him by.

But that changed when Paul Thomas Anderson gave Sandler a loftier conduit for his talents in Punch-Drunk Love. This character isn’t all that far divorced from the essence of the comedic Sandler, but we’re given a decidedly new perspective on the vulnerable personality.

Sandler plays Barry Egan, a lonely bathroom supply business owner living under the shadow of his seven domineering sisters. He falls for a coworker of one of his sisters, but soon finds his hope for love endlessly complicated.

Running afoul of several henchmen who try to extort money from him with threats of violence, Barry’s budding relationship starts slipping from his grasp. His efforts to find the courage and self-confidence to take control of his life make up the heart of Punch-Drunk Love. Sandler gives us a fresh new view of his acting abilities under the guiding hand of a gifted director.


4. Charlize Theron – Monster (2003)

Though Charlize Theron had certainly proven herself a capable and talented actress by 2003, her public image was still that of a glamorous star. But Monster was soon to change that perception when an unrecognizable Theron took on the role of a real life serial killer.

Famous critic Roger Ebert famously confessed to not realizing who the lead actress was until seeing her name in the closing credits. And he can hardly be blamed for the oversight – Theron gained 30 pounds for the role in addition to donning dentures, contact lenses, and a heavy coat of makeup.

But her transformation was not only a superficial one; Theron embodied and humanized the troubled soul of a killer with stunning dedication. Aileen Wuornos was executed in 2002 for the murders of seven men she met while working as a prostitute, and she comes to life in the film Monster.

Theron cared deeply about the character she was portraying, and she cast off all preconceived notions about her prior work as an actress to turn in a towering performance. It’s not only a surprising role for the great actress, it remains one of the most dynamic pieces of acting in modern times.


3. Gregory Peck – The Boys from Brazil (1978)

The Boys from Brazil (1978)

It’s hard to think of an actor who could more effectively represent a wholesome, kind father figure than Gregory Peck. Something about his dignified bearing and manner of speaking just made it easy to assume he was a paragon of virtue.

This made Peck a logical casting choice for films like The Big Country and To Kill a Mockingbird, which solidified his reputation as an actor who could bring real moral weight and authority to a role. So it still comes as a bit of a jolt to witness the great Gregory Peck in 1978’s The Boys from Brazil.

In a movie also starring Laurence Olivier and James Mason, Gregory Peck still manages to deliver a standout performance in perhaps his most unconventional role. He plays Dr. Josef Mengele, a Nazi who creates dozens of Hitler clones in 1960s Brazil and scatters the boys all over the world.

While planning to establish the Fourth Reich, Peck runs afoul of Nazi hunter Ezra Lieberman, played by Laurence Olivier. Watching these two legends face off is too much of a treat to miss, and this battle between good and evil makes for a unique viewing experience carried by its fine performances.


2. Tony Curtis – The Boston Strangler (1968)

Cinema icon Tony Curtis could always boast of a career full of diverse roles. He had long explored characters who lived on both sides of the law, and he was no stranger to almost every available film genre.

Perhaps his most legendary role was in 1959’s Some Like it Hot – an uproarious comedy with Jack Lemmon famous for its pitch-perfect performances. But 1968’s The Boston Strangler found Curtis in an unexpected role which was new for even the veteran actor; in it, he tackled the character of a real life serial killer known as the Boston Strangler to great acclaim.

Playing opposite Henry Fonda as the detective on his trail, Curtis gives a nuanced portrayal of an elusive killer wreaking havoc in Boston. The role required the ability to convey the reality of a split personality, and Curtis found a way to balance the heavy demands.

Both as the disturbed killer and as the friendly neighbor whose victims let him into their homes, Curtis proves his genius. The Boston Strangler was one of his final successful starring roles, and for this Hollywood legend it was a worthy capstone.


1. Henry Fonda – Once Upon a Time in the West (1968)

Frank – Once Upon a Time in The West (1968)

During his long and legendary career, Henry Fonda carved out a special niche for himself playing the earnest, sincere, idealistic everyman. Audiences came to expect that when good and evil were locked in the heat of battle, Fonda’s character would certainly be on the side of right and justice.

His honest, plain-spoken persona seemed set in stone through roles in The Grapes of Wrath, The Ox-Bow Incident, and 12 Angry Men. So it would have been reasonable to assume that Fonda’s casting in Once Upon a Time in the West would have been as a struggling farmer or sincere lawman; but instead, Sergio Leone’s camera focused on the cold, steely blue eyes of Fonda the villain.

While the qualities of this epic Western have grown in public esteem over the years, few ever disputed the great acting it contained. The biggest mark here is left by Henry Fonda, who plays a ruthless henchman determined to take a valuable piece of land from its owners at any cost.

Gone are the compassion and genuine sincerity audiences came to expect from Fonda, and in their place is cold-hearted cruelty. It’s genuinely jarring to see the acting legend in the antagonist’s role, but Fonda pulls it off brilliantly. Sergio Leone deserves credit for his insight into this casting choice, and Fonda delivers an unforgettable performance.