Are we talking Porn video???
If we are, or even if we are not, I think the most engaging conversation would could have would require getting past the "I" factor. I think. I feel. In my opinion. It is impossible to entirely devoid ourselves of our own likes and tastes. The problem with that is everyone has unique likes and tastes. The best way to get at "Best" whatever is to be willing to think on a larger scale. Beyond your liking a video, what video have you noticed that impacted a wide enough audience of varying tastes to all agree that 'this one thing' is cool.
Despite huge, varying opinions MOST people were moved, enjoyed by this one thing.
Or it was a piece that transformed it's genre. Like 2001. Like it or not, no "space" film was ever the same after that movie.
As for porn, the Internet age has a problem competing with the direct to film age or the video tape age. There's so much product and so many venues it is hard for even good porn to have that wide "Frozen" effect. For instance, there have been a great many well lensed twink film, but none had the impact that Bel Ami had with Lucas. Or the way William Higgins transformed the studio blockbuster.
I doubt we have any way to know the profit margins or unit sales/rentals/views of porn in the Internet age to be able to gauge the true impact of porn on the wider audience. We can assume for instance that Str8 Cam Jeff set the bar for amateur porn on the web. And if that's the case certain one of his better scenes would need to be nominated for "best" in the category of Amateur Cam Porn.
Certainly any choices I'd make would reflect a bias in favor of vintage porn. Just as anyone born after 1985 would have a different spin. And my choice of "Best" would definitely be individualistic, from the heart, and most likely not a real candidate for "Best", because best would need to take in a wider set of opinion than my own. It might be useful to separate the eras. As well as the genres.
Here are some award winners from the past. Not a guarantee of the 'best' of that year, but a starting point for discussion. ----????
1984
Pleasure Beach
1985
Sailor in the Wild
Sizing Up
Inch by Inch
Best Friends
1986
Hot on the Trail (JD Cadinot)
The Young and the Hung
1987
Bigger than Life
Power Tool
1988
Big Guns
1989
Too Big For His Britches
1990
Heat in the Night
Carnival in Rio (Kristen Bjorn)
I could list more but in a way is there a need? Have any internet age muscle video come near the classic Colt videos of old? Are there really 'bigger, better' porn films to top Big Guns, Sailor in the Wild, Pacific Coast Highway?
If there are, list 'em. I'll watch them.