30) Airplane 2: The Sequel (1982)
This is one of the many silly comedies that bombards the viewer with as many half-baked jokes as it can in the hope that half of them will stick. And it works. The setting of a passenger jet flying through space on mission to a moon base was novel and provided fertile ground for comedy.
29) Annie Hall (1977)
Woody Allen has made many great relationship comedy / dramas. Usually I find them intelligent, but they don’t have me rolling about with laughter. Annie Hall for me struck a very good balance.
28) A New Leaf (1971)
Walther Matthau’s comedies of the 60’s and 70’s are virtually always good, but this one hardly ever gets a mention. Matthau plays a spoilt-rich scumbag who goes broke and then tries marrying into money with the further intention of killing his new wife and taking her fortune. The film is technically below par and the humour is of the cynical and twisted variety in places, but the ending is a suitable antidote.
27) The Frisco Kid (1979)
Harrison Ford and Gene Wilder star in this very underrated comedy western about a Rabbi on his way through the US who teams up with an outlaw on the journey.
26) Dirty Rotten Scoundrels (1989)
Another film about men trying to fleece a rich woman of her wealth. Michael Caine and Steve Martin perfectly compliment each other’s performances.
25) The Warrior and the Blind Swordman (1983)
Also a contender for dumbest movie ever made. This fantasy martial arts movie isn’t even supposed to be funny, but my whole family and I were in tears and fits of laughter, especially at the final fight sequence. If the humour were intended this would be in my top ten.
24) Monty Python’s The Life of Brian (1979)
Some would choose this as the greatest comedy ever and many would have it in their top ten. Though incredibly funny on first viewing I personally haven’t found a lot of rewatch value in it over the years, hence its low position on my list.
23) The Wolf of Wall Street (2013)
Belly ache laughs to be found in many scenes of this film. Scorsese’s direction and DiCaprio’s acting totally deliver. Great to see a modern movie that revels in being unPC. Film is a bit too long though.
22) Bachelor Party (1984)
Not the smartest of movies, but good adolescent fun all round. Fast pacing and some daring sexual scenarios keep the entertainment levels high. Tom Hanks veers away from his usual wholesome screen persona here too.
21) Pulp Fiction (1994)
Though as much a drama as a comedy PF succeeds in both. First time viewing in cinema was amazing. Whole audience in fits of laughter and word of mouth on the way out to the parking lot was all good. Incredibly smart use of racial humour too.
20) The Naked Gun (1988)
The second Leslie Nielsen film on my list. Lots of crazy set pieces from a car chase with a learner driver to the protagonist holding onto a statue’s concrete penis to avoid falling to his death.
19) Trading Places (1983)
Like The Life of Brian, many would put this close to the top of their list. It’s brilliant, but some of the jokes wore thin on me in repeat viewings. A good glimpse into the stock markets mixed into the story too.
18) As Good As It Gets (1997)
Jack Nicholson’s funniest performance for me (One flew over the Cuckoo’s Nest just fell short of my list as it’s quite a serious movie with comedy overtones). Tightly scripted, lots of cringe-worthy insults, yet has its heart in the right place as well.
17) The Nutty Professor (1963)
Jekyll and Hyde comedy. Jerry Lewis, when he was on form, is one of my favourite comedians, but also talented generally. He wrote and directed this and many other films as well as starring, and even pioneered the technology for directors to see their own rushes on set instead of waiting until they got to the cutting room. Playing as the character buddy Love in this movie he is amazing, but his parallel role as a goofy professor is hit and miss. Eddie Murphy’s remake is worth a watch too.
16) The Big Lebowski (1998)
Packed with little hidden jokes and cryptic plot elements, this movie has high rewatch value. It’s a great social satire all round.
15) The Man With Two Brains (1983)
Steve Martin goes for all out silliness and a lot of sexual humour. Kathleen Turner shines as money grabbing villainess.
14) Porky’s (1982)
Often looked down upon for its objectification of women, this movie is much smarter than its critics would like to admit. Quality acting from a great cast, surprisingly effective drama, and fierce anti-semitism themes that are good but a bit overdone. But when the film goes for the full comedy effect it hits several home runs.
13) There’s Something About Mary (1998)
This soppy love story is expertly balanced by brutally cruel humiliation-based comedy scenarios. Many a classic scene.
12) The Sons of the Desert (1933)
Laurel & Hardy were apparently, in real life, sick of being asked to join the Freemasons. So they made this comedy about two bullied husbands lying to their wives so they can attend a Masonic ball. Result is some of their finest material.
11) Clerks (1994)
Kevin Smith’s debut ultra-low budget comedy still knocks the hell out of everything else he’s ever done and it produced a failed, but very funny, cartoon spin off that ran for just one short season. Clerks is daring, honest and insightful.
10) Cactus Flower (1969)
Another Walter Matthau relationship comedy that few have seen or even heard of these days, but it’s a gem. Plot structure and dialogue are exceptionally well thought out.
9) Liar Liar (1997)
Jim CareyI often find to be a pale imitation of Jerry Lewis, but this movie tops any of the latter’s efforts. The super sharp script about a shady lawyer who wakes up one day unable to lie is so intelligent and earnest that even a mediocre performer could have done something with it, but it’s a perfect vehicle for Carey’s goofy physical humour. Outstanding scene, Carey insulting a boardroom full of executives.
8) Revenge of the Nerds (1984)
This movie would have been a mega commercial hit had the executive who gave it a limited release (and was fired for doing so) realized what a great movie it was. A creative cast of relative unknowns were given a great deal of freedom, resulting in a whacky mix of inspired humour. Like Porky’s (number 14 on this list) this film pushes hard for an anti-bigotry message, but contradicts itself. It includes a questionable date rape scene that’s treated as no big deal, and the efforts to demonize jocks are so off the scale that they actually add to the comedy.
7) Pardon Us (1931)
Laurel and Hardy go to jail for selling liquor under prohibition – how could this result in anything other than one hilarious scene after another. Available in multiple versions, the longest cut (70 mins) is the best.
6) Sleeper (1973)
The second Woody Allen item on my list is unique among his filmography because it’s also science fiction. Frozen for 200 years, Allen’s character awakens in a future society of dumbed down people and assists in a revolution. It’s very smart and very funny.
5) The Jerk (1979)
Steve Martin’s third entry on this list is a satire of many things including detective stories and the rags to riches American dream. It’s very childish in places, yet brutally cynical and crudely sexual. Even Stanley Kubrick loved it.
4) Way Out West (1937)
Third Laurel and Hardy film to make this list. This one is as heart warming and sweet as it is funny. Their brand of humour is far more intelligent than it is generally given credit. Also directed by Stan Laurel.
3) It’s A Mad, Mad, Mad, Mad World (1963)
This movie is a good three hours long, but it’s anything but slow. Ensemble cast playing very well written characters. Packed with impressive and hilarious car chases and other stunts. Tons of physical humour and a big middle finger to money grabbing materialists. The size of the production and ambition of the story is remarkable.
2) Duck Soup (1933) (or any of the Marx Bros. best movies)
My first write up of this list included seven Marx Bros. movies, so I decided to make them occupy just one position on the list to make room for others. Duck Soup is probably the best, but Monkey Business, Horse Feathers, A Day at the Races and a handful of others only fall marginally behind it. Their humour was physical, satirical, even sexual in ways the censors probably missed. And they absolutely had it in for posers among the rich. Any of these films will provide you with a bag full of insults to fend off pretentious snobs.
1) Monty Python and the Holy Grail
I’m still unsure whether to place this or the Marx Bros in the number one spot, but for now I think The Grail wins by the tiniest margin. It’s wildly experimental, messing even in the opening titles with the traditional movie narrative structure as it parodies the artificiality of historical adventure epics. Like the Marx Bros at number 2, Grail is a big shout out against elitist snobbery with even the time setting of the film shifting from the past to the present as the deluded “King” gets carted off at the end in a police van and probably to be placed in a mental institution. For me this is the undisputed crowning glory of the entire Python filmography.