The 10 Most Entertaining Movies of All Time

One of the many virtues of cinema is sheer entertainment value. Not everything has to be deeply thought provoking or life changing. Although there is bound to be an overlap with some if not all of the movies on the list given the subjective nature of cinema.

This list ranges from dark comedies to light-hearted crime capers with many other genres in between. They all have one thing in common though: They are all endlessly re-watchable, whether it’s thanks to quotable dialogue, memorable characters or an engaging plot, or all of the above.


10. The Wolf of Wall Street (2013, Martin Scorsese)

This biographical crime comedy is wildly entertaining, gleefully raunchy and unforgivably excessive. Leonardo DiCaprio is backed by the likes of Jonah Hill as his just-as irresponsible sidekick and Margot Robbie as his neglected trophy wife amongst others such as Rob Reiner, Kyle Chandler and Jean Dujardin. There is also quite a memorable appearance by Matthew McConaughey as a chest-pounding, highly motivated Wall Street broker.

Leo never shies away from realising this despicable character or his deplorable lifestyle. It might just be his most demanding performance, rivalled only by his turn in “The Revenant”. The sheer amount of work asked of the actor by the film ranges from the self-referential, fourth wall shattering narration to the drug-fuelled slapstick and of course a healthy dose of motivational speeches to boot.

The events portrayed are so over-the-top to the point where you forget that what you’re watching is a biopic… I guarantee you that you will not find another film where three hours fly by so fast. It’s an absolute cinematic roller coaster to say the least. This leads to all sorts of debauchery involving drugs, hookers, massive parties 24/7 and of course using midgets as lawn darts.

Impeccably crafted as we’ve all come to expect from Scorsese, it’s very hard to believe that a film as energetic as this was directed by a man who was in his late 60s at the time – making it perhaps the strongest argument against anyone of the stance who says that the master filmmaker has lost his touch.


9. Snatch (2000, Guy Ritchie)

After somewhat establishing himself as Quentin Tarantino’s British counterpart with his 1998 hit: “Lock, Stock and Two Smoking Barrels” – Guy Ritchie set to outdo himself with another London-set crime caper with interlocking threads. Only this time, it would be even bigger and better…

The result? “Snatch” – one of the most endlessly re-watchable and quotable flicks of the 2000s. Thanks in large part to a sprawling yet neatly woven plot, sharp witty dialogue and an impeccable line up of perfectly cast actors, including Benicio Del Toro, Brad Pitt, Jason Statham, Stephen Graham, Alan Ford, Vinnie Jones and the always welcome Denis Farina amongst many others.

The beautiful thing about the characters is that they all get a fair share of screen time and none of them are overshadowed. They all stand out and could easily each have a film to themselves.

Another key strength of course is Ritchie’s stylised, music-video-esque direction which captures the scummy, grimy atmosphere of the story’s criminal underworld perfectly without taking itself too seriously.

On the first viewing, the movie might be hard to keep up with but this is one of the many reasons why it is so enjoyable, it keeps you on your toes and is one of the best examples of what hyperlink cinema can accomplish with a killer soundtrack and plenty of dark humour sprinkled throughout.


8. The Sting (1973, George Roy Hill)

The Sting

In a decade filled with films that exhibited modest doses of blood and gore, the landscape of the crime genre was rapidly evolving to meet this new-found level of extremism but in 1973, along came a playful, charming and light-hearted caper that saw the re-uniting of director George Roy Hill with stars Paul Newman and Robert Redford, who had previously all worked together on “Butch Cassidy and the Sundance Kid”.

That film is of course, “The Sting” – quite possibly the finest con flick ever to come out of Hollywood, it fools everyone including the audience.

Newman and Redford’s chemistry is undeniable and they work brilliantly together with neither one trying to upstage the other, a problem that’s prone to occur when two stars of that calibre co-star. They also work superbly individually and each of them manages to create a likable character. There is also much to be said of Robert Shaw, who plays the Irish crime boss and the two con men’s target, Doyle Lonnegan. Truly a great performance, Shaw doesn’t have too many scenes but he still manages to create a properly imposing villain nonetheless and fully realises the threat of his character.

There is nothing deeply profound or thought-provoking about The Sting – it just happens to be one of the most enjoyable films of all time, it has everything you could want from any caper: style, character, humour and of course, a catchy score. It can be watched at any point at any time of day by anyone and stands as one of the most indelible and delightful Hollywood flicks ever made.


7. North by Northwest (1959, Alfred Hitchcock)

The crop duster sequence in North by Northwest

“North by Northwest” was screen legend Cary Grant’s fourth and final collaboration with Alfred Hitchcock and it just might be their most memorable together.

This movie is an outrageous culmination of Hitchcock’s tried-and-trusted “wrong man” motif with a plot that becomes so intricate and layered that it very nearly reaches the point of self-parody. Even the film’s screenwriter, Ernest Lehman once said that he wanted to pen; “the Hitchcock picture to end all Hitchcock pictures”.

The screen legend that is Cary Grant creates a caustic yet likable protagonist with Roger Thornhill, an ordinary man who gets caught up in a series of over-elaborate misunderstandings. It’s one of his finest performances and shows that he could have easily portrayed James Bond, a character whose film franchise owes a lot to this classic.

Filled with iconic imagery from its crop duster scene to its climax at Mt. Rushmore, North by Northwest is a film that has been endlessly parodied and paid tribute to while remaining a classic which has inspired many since its release.


6. The Good, the Bad and the Ugly (1966, Sergio Leone)

Here we have a strong contender for not just the greatest spaghetti western of all time but also quite possibly the greatest film of all time. Sergio Leone directed five westerns throughout his career and “The Good, the Bad and the Ugly” is often cited as being his crowning achievement, although a case could also be argued for “Once Upon a Time in the West” or his gangster epic, “Once Upon a Time in America” but that’s another list for another day.

Probably the finest example of a score complimenting the visuals of a film, thanks to Ennio Morricone’s unforgettable work as composer and conductor, which helps give the film a certain operatic quality. Every piece of music is an amazing accomplishment in its own right and Leone knew exactly when and where to use each composition throughout to enhance his film without depending on in, a trap which many directors seem to fall for when blessed with such a talented musician.

Clint Eastwood bids farewell to his iconic role of The Man with No Name while character actor Lee Van Cleef portrays one of the most ruthless villains in cinematic history but by far, the man who completely steals the show is Eli Wallach who plays “The Ugly” Tuco Ramirez – who is quite simply a dirty, rotten but loveable bastard. A highly entertaining performance in every regard; he’s uneducated, uncivilised yet deceptively intelligent and he demonstrates this in a handful of scenes such as the famous bathtub scene. It’s a very hard performance to forget.

Every element of the film is on par with the music and performances; the cinematography, the editing, the breathtaking locations and the writing, which has an episodic aspect to it that makes every scene memorable in its own way but never loses sight of the plot, which in essence, nothing but a treasure hunt and it’s all of the film’s elements that work together to make the film so entertaining and easy to revisit.