Comedy might be subjective, but whether or not a joke is going to stand the test of time is a lot easier to analyze. An overabundance of pop culture references might pay off in the short term, but hurt it in the long term. And offensive jokes are well and funny when utilized well, but if they are lacking self-awareness or go too far, they can ruin everything.
Here's a rundown of a few comedies from over the years that have shown their age, and a few to counter them, with five surprisingly timeless entries.
Timeless: Dr. Strangelove
With the ghosts of the Cold War popping up to haunt the world every few months, there's a sort of sadness attached to the fact that Dr. Strangelove will always be relevant. The governments of the world will always be incompetent, they will always look out for themselves first, they will always resort to unsavory methods to get things done, they will always settle for half-measure or pat themselves on the back for doing nothing.
Say what you will about Stanley Kubrick's method, but his insistence on making every film of his into a masterpiece has always worked.
Less Relevant: Goldmember
Austin Powers franchise itself is pretty dated already. There's nothing too awful about Goldmember, it simply has shown its age, is all. The running gags from the first two films are a little more worn down by this entry, and it feels like a paycheck to earn off the successful franchise, rather than a needed entry.
The real question is if the dated jokes were intentional or not - it certainly seems somewhat self-aware of the needlessness. Just in the opening scene alone, there is a plays Dr. Evil, which some may say is a suitable moniker for the disgraced actor.
Timeless: The Big Lebowski
certainly is a movie of the 90s era, but the way it approaches its story and the execution of its absurd and meandering jokes make it a perfect comedy, even decades later.
It doesn't feel like a 90s comedy, so much as a nostalgic feel-good comedy that carries a timeless message. In fact, it has a mythical aura to it. The film has garnered a massive cult following and even has inspired a small religious following which honors the film in its philosophy, which is just more proof that it's a modern legend that continues to inspire.
Less Relevant: Breakfast At Tiffany's
Yikes. Unlike the use of Blackface in used by the filmmakers to highlight how offensive it is and was more than self-aware, the problem with Breakfast at Tiffany's is that Mickey Rooney's "yellowface" is exactly the kind of clueless, offensive material that Tropic Thunder was lampooning.
The only non-white character (in New York City) is played very offensively by a white actor and plays off every stereotype. There's no purpose to the character, it's just a racist gag.
Timeless: Monty Python And The Holy Grail
For a movie set in the Middle Ages, lives up to its own name for being the holy grail of loose sketch comedy films. The film's absurd and silly humor makes it impossible to take anything the movie does seriously and it has been quoted by cinephiles, historians, and nerds ever since its debut.
There are no pop-culture references, there isn't anything inherently offensive, and is so light-hearted and silly that it can be liked by most anyone.
Less Relevant: Big
Let's just address the elephant in the room immediately: Tom Hank's character, a 13-year-old, turns into an adult (physically), and ends up sleeping with a woman later in the film. A lot of movies have bounced around with the idea of a child getting frisky with an adult, such as Blank Check or Milk Money, but few have the gall to have the kid do the deed.
And yet, Big went for it, and still managed to be a whimsical and wholesome movie ... besides the whole (unknowing) statutory rape hurdle.
Timeless: Blazing Saddles
Many films in Blazing Saddles. All the racism and gags in the movie are highlighting the idiocy and contradictory nature of racism, and like all Brooks' films, makes the racists the butt of the joke, not the people of color.
It's also a great satire of the idealized Westerns that helped contribute to many people's misconceptions about history, and it contains one of the greatest fouth-wall-breaking-scenes put to screen.
Less Relevant: Animal House
If ever there was a film that contributed to the decline of the college campus, it would have to be Animal House, which built up college to be nothing but frat parties and debauchery. That's fine and well, but the boorishness of the film has stained it a bit.
There's a lot of sexist and homophobic language, a professor sleeping with a student, a few racist gags, and worst of all, a scene where a frat member looks down at a half-naked drunk girl and debates whether or not to rape her while she's unconscious.
Timeless: Planes, Trains, And Automobiles
Out of John Hughes' entire filmography, Planes, Trains, and Automobiles might be his most heartwarming and well-rounded movie. The journey of Neal and Del trying to make their ways home while dealing with each other and building a friendship in the process, despite their vast differences, makes for the perfect buddy comedy.
The film is drenched in a sort of 80s nostalgia, and everything that the era entailed, and the viewing experience, is akin to watching a home movie of someone's 1987 Thanksgiving (albeit with some wackiness). And who doesn't like to pull out the home movies every once in a while and fondly look back?
Less Relevant: Revenge Of The Nerds
Once again, another film on this list tries to make rape a source of comedy. In this case, the beleaguered and bullied nerds at a university decide to get even with the jockish frat that has been harassing them.
How do the get even? For starters, they sell pies with naked pictures of the frat and one of their girlfriends. Then, at a costume party, one of the nerds dresses up in one of the frat ' outfits and has sex with the unwitting girlfriend, revealing he is not her boyfriend, but one of the nerds, only after having sex with her. And that was funny ... how?
