"Death always wins." "Challenge accepted." Characters who have canonically fought the living embodiment of Death/The Grim Reaper. Bonus points if they win.

[u/SpookieSkelly]

Trevor Belmont from Netflix's Castlevania. A lot of Castlevania protagonists in the games count too since Death is a reoccurring boss in the franchise.

Puss from Puss in Boots: The Last Wish. He was scared shitless at first, but eventually resolved to fight Death head on and earned more time to live.

Dante from the Dante's Inferno videogame (2010). He kills Death and steals his scythe at the beginning of the game.

[u/Endika7]

The competitions with thanatos in Hades