Cribbage dates back to the early 17th century and appears to be an improvement  of a game called 'Nobby'. Which has a similar scoring scheme but without the 'crib', which is really the soul of the game (as you can tell from the name).

Around 1630, the new rules were devised (or at least published) by Sir John Suckling, an English poet and gambler. He is said to have sent out decks of marked cards and later cleaned his 'marks' out playing cribbage (a sum of 20 000 Pounds is mentioned - in the 17th Century a massive sum).

The game grew very popular in England and later, via English settlers, in America. In 1980 the American Cribbage Association was formed to organize national tournaments.

The game is mentioned in the Dickens novels  'The Old Curiosity Shop' and 'Oliver Twist' (and also by Jane Austen). Though I first came across it in Robert Heinlein's book 'Tunnel in the Sky' (in High school).

The best score in one hand is 29 - 3 fives and a jack, with the starter card the other five and the same suit as the jack - 'The Perfect Hand'.
There's a story that during WWII,  Commander Morton of the submarine USS Wahoo dealt a perfect hand to his Executive Officer, o'Kane. This was  considered a lucky omen and o'Kane had the five cards signed by other officers and later framed them. There is now a tradition that the Cribbage board  used in that game is passed on to the oldest active submarine - currently the USS Bremerton.

Some games just naturally gather legends.