As a longtime Marvel fan, one thing I have always wondered: Has Deadpool ever fought Thanos? After all, in the 'Funeral for a Freak' storyline, Thanos is shown so jealous of Death's love for Deadpool that he curses the Merc with the Mouth with immortality, claiming he will "never feel Death's loving embrace". However, I have yet to see any actual fight break out between the two. Any help would be greatly appreciated.
If nothing else, 2015's Deadpool vs. Thanos opens with the end of a fight scene:
Similar to the recent Deadpool's Secret Secret Wars, there's a jumbled chronology approach to the story that cuts between a hyper-violent reunion between the two characters and the events leading up to that encounter. It does seem like that approach is more trouble than it's worth in terms of setting up up this pairing. This is more a team-up story than a real, extended battle between Deadpool and Thanos, but this entire opening chapter is devoted to setting the stage for said team-up.
It goes about as well as you might think.