JoCo Cruise Crazy

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In October 2009, Jonathan Coulton mentioned the "hypothetical" possibility of hosting a cruise involving entertainment by himself and his "circle of famous entertainment powerhouse friends." After evaluating fan interest in such a venture via the blog, the cruise was announced as a real event in July 2010. In a nod to JoCo's song Tom Cruise Crazy, the event was dubbed "JoCo Cruise Crazy".

The inaugural JoCo Cruise Crazy sailed the Caribbean in January 2011, with approximately 375 attendees (often referred to as 'Sea Monkeys'.) It was deemed such a success by performers and fans alike that the organizers quickly began planning a sequel. JoCo Cruise Crazy 2 was announced in April 2011, and sailed February 19-26, 2012. Joco Cruise Crazy 3 was announced before the ship returned to port, and pre registration made available to those onboard.