Becoming dated is not helpful. But there are ways to avoid becoming dated.
This page gives tips on how to make sure you have an audience and continue to do so as years pass.
This is a simple suggestion that does not particularly require further explanation. It will be built upon by the following tips, however.
I learned this the hard way with a comic strip I once drew, in which the main characters, the Comic Five, would sing song parodies written about what was happening in the strip at the time. However, events and subplots came and went, which meant that eventually the parodies were no longer reflective of the times. This prompted the Five to do two albums over again, which would have been a good plan had they not moved away from singing about general activities and subplots and toward singing about exact individual strips. Having gone the wrong direction, they suffered the exact same fate again.
This was one of the reasons I eventually decided to make all my parodying fit the official Pirates of the Caribbean canon. I reason that this way, my parodies cannot become obsolete, at least not in the same way. This also bears mentioning that in general, movies are a better subject than, say, video games, as movies are easier for more people to experience, can be experienced in more different ways, and are more likely to be remastered for more advanced technology.
You will find that I have a Parodies that are accessible to everyone
category, for good reasons. Most, however, are niche horror stories like Yellow.
But millions of people will recognize the enemy of the Black Pearl squid-faced.
I can imagine the reaction from those who do not, but I have included links to what my parodying is about in order to help them.
The Comic Five mentioned in Tip 2 were notorious for mixing and matching all kinds of things they knew my readers would get, heedless of whether those things were compatible or complimentary. The worst case of this in the parodies was Half Camping, Too Much Camping,
which was half about the character Roger Fox from the comic strip Fox Trot and his bad vacation plans, half about the cartoonist
(me) and how I was going on what would no doubt be a much better trip. Plus, the cherry on top of this sundae of trouble was saying spend gold studs
to refer to the currency in the video game they were based on, even though there was nothing else Lego about the rest of the parody.
So, as you can see, it helps if the parodies can be their own context, and you are well advised to keep the need for anything from without to a minimum. Having to include links to pages about what the parody is about is fine, but usually you should not have to write the explanation yourself. Also, mixing multiple unrelated things in one parody just makes it so the audience has to happen to know what all of them are.
I have noted with interest that I have never parodied anything from before the 1970s, and speculated that part of the reason is that songs from that era are not popular enough these days. With my song selections mostly being ones that are multiple decades old, I have acknowledged that it might not be the most relevant in general, but I will point out that most, if not all, the albums I have done had at least one hit song that may have drawn any number of others to get them. Certainly, for instance, all those Styx albums had some connections. And while I was at it, I dabbled a bit with the long-extinct genre of prog rock, but avoided the extremes - no songs that break the 10-minute barrier appear on my site. (This would be good for any parodist, as a song of such abnormal length would be easy to get lost in, and the resulting parody would not have a large audience anyway.)