Thing about video game strategies is, they're always helping you win. What's the deal with that? What if you want to find the most spectacular routes to glorious failure possible? Well then, look no further.
Muselk has an ongoing series of videos in which he selects the worst possible weapons for each TF2 class and then plays matches with them. The results are rarely pretty. For instance, the above video has the Pyro with an objectively worse-than-usual flamethrower and a gun that takes advantage of water... on a level with no water. It goes about as well as you'd imagine.
And here's the typically crafty Demoman as some kind of awful flying sword wizard. This one actually went kinda alright in places, if only because I think other players were ensnared by confusion, not so much deer-in-the-headlights as someone about to be hit by a single, person-sized meteorite staring up and going, "why."
The flying Scout is another example of a terrible loadout actually working a little, in large part because, man, he can really get around. If you want to deal very little damage but move like a greased pterodactyl, well, here you go.
And then there's this Spy loadout, which actually ended up being kind of really good. Whoops.
So that's fun. Nothing like the intentional comedy of awfulness being countered by the unintentional comedy of awfulness turning out to be great. It says something (good, I think) about the design of Team Fortress' zany arsenal that outside-the-box loadouts can still be decent-ish under the right circumstances.
What's the worst loadout you've ever played with? Did you... did you do it on purpose?