Trained, professional killers have always been a major part of pop culture, whether it's in movies or video games. There is something strangely alluring about characters who pursue murder-for-hire as their way of making a living, whether willingly or by coercion. Of course, assassins are not always motivated by profit. Some of the best action movies ever made told a story of killers on personal or professional vendettas.
However, even the most skilled assassins fall prey to certain vices, which can render them awful at their job. Whether it's love, self-adulation, arrogance, or even simple forgetfulness, there are plenty of films out there in which trained killers make rookie mistakes that eventually lead to their downfall.
10 Darth Maul (Star Wars: The Phantom Menace)
The character of Darth Maul is a very interesting figure, especially taking into account his stints in the comic books and the Clone Wars animated series. It's unfortunate that his only appearance in live-action Star Wars movies was The Phantom Menace, which is arguably one of the most confusing and disliked episodes of the revolutionary saga.
His primary assignment in the first episode of the prequel trilogy was to capture Padme Amidala and later to kill Qui-Gon Jinn and Obi-Wan Kenobi. While he did manage to assassinate the Jedi master, the over-confidence in his own abilities led to him underestimating the skills of Obi-Wan, who eventually ended up using Maul's brief moment of inattention to put an end to the Sith Lord's life (for a time) by slicing him in half.
9 John and Jane Smith (Mr. and Mrs. Smith)
Mr. and Mrs. Smith is a movie of huge cultural significance, not because of its critical acclaim or its impact on the art of cinematography, but because it established Brad Pitt and Angelina Jolie's relationship as a couple, giving rise to the famous "Brangelina." The film's plot revolves around a married couple of trained assassins working for competing agencies, tasked with murdering each other.
The main premise of this story is also a dead giveaway of the Smiths' unprofessional approach towards their trade. On the one hand, it may seem impressive that they've managed to keep their true professions a secret from each other for so long, but on the other, it is quite embarrassing for a highly-skilled secret operative to be fooled by the same tricks they employ on a daily basis.
8 Frank Falenczyk (You Kill Me)
Ben Kingsley's character in You Kill Me certainly deserves a lot of compassion, but in all honesty, Frank Falenczyk seriously compromised the Polish mob (his employers) during his stint as their hitman. His failure to carry out a critical assignment was mainly due to his drinking problem, which may have suggested that he was not the best-suited candidate for a murderer-for-hire in the first place.
You Kill Me is an underappreciated comedy where an assassin who is awful at his job undergoes a journey of self-discovery and improvement, becoming a better killer as a result. It's a clever spin on the formula of assassin-themed movies where the hitmen start out extremely competent but end up behaving unprofessionally all throughout the film.
7 Travis Bickle (Taxi Driver)
Taxi Driver is widely considered one of the best movies in the history of cinema, but it contains one of the poorest assassination attempts ever planned. Travis Bickle may not have been a professional murderer-for-hire, but he certainly trained like one throughout the duration of the movie.
All the time spent on getting physically fit, scoping out his target's security, and obtaining the guns necessary to carry out the assassination of Senator Palantine were wasted almost as soon as Travis got to the rally location and let himself get spotted by Secret Service agents.
6 Vincent Vega (Pulp Fiction)
As far as movies that follow hitmen are concerned, Pulp Fiction has got to be one of the most iconic pictures on that list. John Travolta's Vincent Vega and Jules Winnfield (Samuel L. Jackson) are an unforgettable duo of assassins who got the job done, but were not the most disciplined when it came to staying focused and vigilant on the job.
On top of accidentally shooting a man in the head, Vega's forgetfulness led to his eventual demise, as he forgot to take his gun with him to the bathroom at his target's house. Vigilance is one of the most important qualities of a good assassin, but Vincent Vega could hardly be called vigilant.
5 Jango Fett (Star Wars: Attack of the Clones)
Jango Fett's example proves that even genetic engineering can't compare to the power of the Jedi. It can be argued that in Attack of the Clones, Jango was doomed to fail, given the chaos of the battle of Geonosis and the high profile of his target (Senator Padme Amidala) and the Jedi knights that were tasked with protecting her.
While more than capable of tracking down and killing targets who were at his skill level, Jango, like many other incompetent assassins, overestimated his abilities and ended up getting beheaded by Mace Windu without putting up too much of a fight.
4 Vincent (Collateral)
Based on the incredibly intriguing premise of following a contract killer around on his typical night on the job, Collateral is a great movie that, unlike any other film, dives deep into the psyche of hitmen. As Vincent continues to kill off the targets on his list in a cold-blooded manner, he opens himself up to Max, a taxi driver he hired to drive him around LA for the night.
Trusting an anonymous cabbie turned out to be a fatal mistake for Vincent. When Max uncovers his final target to be a woman he befriended at the beginning of the movie, the pair engages in a deadly shootout on an LA Metro train. Max comes out victorious, leaving Vincent to die on the train.
3 Boba Fett (Star Wars: The Empire Strikes Back and Return of the Jedi)
Just like his father, Boba Fett has fallen prey to his own insufficient abilities, although to be fair, he managed to be much more of a match to his foes than Jango did.
In The Empire Strikes Back, he successfully tracked down the Millennium Falcon and its captain, Han Solo, and turned him over to Jabba the Hutt. In Return of the Jedi, in a highly unprofessional manner for a bounty hunter, he ends up getting eaten by a sarlacc near Jabba's palace on Tatooine by a blind Han Solo, who accidentally sets off Fett's rocket pack and sends him flying into the beast's mouth.
2 James Bond
As one of the most famous spies in movie history, James Bond surely can't be called "awful" at his job. After all, he successfully managed to complete difficult missions and get himself out of sticky situations across 25 movies. Many of these situations, however, could have been avoided if not for Bond's brief bouts of incompetence.
His affinity for chasing after women and over-confidence in his own abilities nearly cost him his (and his superiors') lives on a few occasions, such as that one time in Skyfall, where Raoul Silva managed to trick the superspy into taking him to MI6 headquarters, which allowed him to gain access to the agency's servers.
1 T-800 (The Terminator)
Arnold Schwarzenegger's T-800 shouldn't have had too many problems carrying out his assignment in the firstTerminator movie. As adeadly, emotionless robot from the futurethat was sent to kill an unwitting college student, Sarah Connor, his failure to outsmart Connor is a testament to Skynet's android killer's incompetence.
He ends up getting crushed by Sarah in a hydraulic press, embarrassingly failing in his quest to prevent the birth of John Connor. The T-800 model returns to the saga in Terminator 2: Judgment Day, and it is safe to say that he suits the role of a protector much more than that of an assassin.