10 Movies Where You Want The Villain To Win

We’re bad people for thinking this way…

There Will Be Blood Daniel Day Lewis

Everyone loves a bad guy and nowhere is this more true than the medium of films. Excellent villains have graced our screens from the very early days of cinema right the way up to our modern obsession with antiheroes. One needs to only take a look at the success of the Venom movies or the legacy of shows like Breaking Bad for evidence of this.

It takes a special kind of villain to truly win our hearts, however. A villain so compelling we root for them to win. A synergy of good writing, good narrative and (above all) an excellent performance are all required to get us truly ‘on side’ with a cinematic antagonist.

We’re not just talking about flawed heroes, either. Taking into account their moral, ethical and lawful shortcomings, we’re going to take a look at some of cinema’s most endearing big-screen bad guys and why exactly they got us wanting them to win; consciously or unconsciously.

10. Joker

There Will Be Blood Daniel Day Lewis
Warner Bros.

The Joker has a long and storied cinematic history, with acting heavyweights like Jack Nicholson and Heath Ledger taking iconic turns as the clown prince of crime. In 2019 the excellent Joaquin Phoenix stepped up to the plate to give us a Scorsese flavoured take on the iconic villain, in Todd Phillips’ Joker.

After making a name for himself in comedies for nearly twenty years, Phillips examines the troubled clown-for-hire, Arthur Fleck, and what social circumstances lead to a tragic figure such as this becoming the Joker. Arthur’s inevitable, violent implosion occurs after he is unjustly vilified by his fellow comedians, abused by the system meant to be fixing him and generally treated as a second class citizen.

The setting of Joker is a thinly veiled simulacrum of '70s New York, a time of extreme crime levels, social deprivation and violent upheavals. The film forces us to question how we would likely act in the shoes of Fleck, living in such a pressure cooker day-to-day.

Whilst not totally sympathetic - he does brutally murder a few people after all - Phoenix’s performance elevates Fleck’s character into someone recognisably human, worthy of your empathy. The catharsis Fleck feels as he makes his final transformation into the Joker becomes catharsis for the audience who have joined him on this brutal journey.


Total goblin. Quit the food and beverage industry after ten years to try my hand at writing nonsense online. I have a huge passion for film, television, cats, art, tattoos, food, anarchy and classic literature (mainly Dune). Currently based at my mum's house, I can be best reached on Instagram (@charlie_marx) where I attempt to soothe my mental health with memes.