Calligraphy, like graphic design, is full of mediocrity. But there are some people who are doing it really well, in more creative, less formulaic ways. The following are the artists I admire.
Jessica Hische is a powerhouse of type design. Bow before her! If I can someday be half as good as her, I'd be satisfied.
Gemma O'Brien is another total badass who take type to a BIG commercial level. By BIG I mean murals.
Timothy Goodman does really fun sharpie-style art. I like how he bounces between messy-yet-super-slick enormous compositions, and actually-messy stream of consciousness ramblings.
Jeff Canham does really neat sign painting. I actually came across his portfolio when I was in college (!) and have kept tabs on his work since. Not in a creepy way.