This is The Hobbit/Edge of Tomorrow crossover written for fun and zero profit. The idea took my brain hostage and threaten to eat it until I wrote this down. If you like the result, please leave a comment.
The first time Bilbo dies, it happens in a cave deep in the Misty Mountains. The air is damp and stale, and it adds an unpleasant taste to the salty blood from his split lip. Dizzy and disoriented, Bilbo isn’t as fast as he should be when he draws his sword. The terrible creature, Gollum, pelts him with rocks, muttering to itself about all the ways it’s going to cook Bilbo, its spindly arms possessing deceptive strength for its malnourished body. And while Bilbo cringes and dodges as best he can, he is too slow. His vision swims, and the cave floor buckles under his feet. One of the rocks hits true, colliding with Bilbo’s temple.
The last thought he has is about the curious little ring he put in his pocket.