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Another character that has long been in the gestation phase for his own movie, Fox even went as far as to tease the return of the character in 2009's X-Men Origins: Wolverine. Deadpool is the kind of character that really could do well on the big screen, but only if they sell him in a way that the general public could understand. Sure, those of us in the geek community get that he's a mouthy, potentially schizophrenic, mercenary that favors pop culture references and mass carnage, but how can you convince regular movie goers that this would be a fun way to spend a Friday night and not a total waste of their time?
The best examples I can think of for something remotely similar to how a Deadpool movie would probably be are the movies Kick-Ass and Shoot 'Em Up. Kick-Ass draws obvious comparisons because of its comic book basis, but its also one of the only hard-R superhero movies and it almost managed to make $100 million worldwide. Shoot 'Em Up, a future cult classic in my opinion, has some of the best staged over-the-top action sequences ever committed to film. What's worrisome about these comparisons is of course that neither of these movies were huge successes.
Will it ever happen? It's a coin toss as far as I'm concerned. A Deadpool movie may not line up with the films they have planned for the rest of their Marvel licenses and they're just playing coy without outright saying “No.” The latest updates for the film don't give much hope either as the script has been written for years and a test reel was shot in 2011, but there's been no movement since then.