No, Doc Holliday and Calamity Jane were both in the West during the second half of the 1800s though. Jane spent most time in the North-Midwest to the Northwest (Utah, parts of Colorado, Montana) while Doc Holliday spent a majority of his life in the Southwest and in the East. Doc died in Colorado, but there is no existing documentation suggesting that Jane and he had ever met. However, it is likely that they may have heard of one another like everyone else (penny trades, newspapers, word of mouth, etc).
They were also represented, albeit in a historically incorrect way, in TV as knowing each other in an episode of Bonanza.
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John Henry (Doc) Holliday was a real person- perhaps not the person shown in movies. The link below will take you to an article on Doc.
Pneumonia in New York City
Yes he did, and eventually led to his death. However the alcohol didn't help.
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The actor who played Doc was Courtney B. Vance.