X-Men Origins: Wolverine
The amazing X-Men: First Class proved that prequels can work when done with style and a love for the source material. Before that, however, was the disastrous X-Men Origins: Wolverine, which proved that even an indestructible killing machine can be dreadfully boring. To be fair, Hugh Jackman is a great actor and I still stand by his portrayal of Wolverine, but this movie is awful.
Whether it’s the heart or the script that is lacking here, it hurt the production enough to make absolutely nobody care about Logan. He is indestructible and stronger than pretty much everyone else in existence (or at least those who oppose him), so why should we care what happens to him? Despite having bones of adamantium, he has a heart of crinkled up paper, and this is how they try to drive the plot forward.
But of course this doesn’t work, because nobody watches Wolverine for his monologues on heartache and love long lost. So making a prequel based on how sad he is and how much of his life has been suffering makes as much sense as fighting the man with a wooden spoon.