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The idea of sailing around the world is certainly a romantic one. Experience is one key to success. So is a good boat. And if it’s going to take nearly a year for you to do it, a companion may save you a later trip—to a psychiatrist. Donald Crowhurst had none of these things in 1968, when he entered the Golden Globe race, a solo, round-the-world sailing competition sponsored by the London Sunday Times. The consequences of that trip fuel the sad but juicy documentary Deep Water. Crowhurst was a faltering businessman with a wife and four children who, desperate to stave off the poverty he grew up with, thought he had a chance to nab the contest’s cash prize. Despite having sailed only recreationally in the past, he pit himself against eight other experienced entrants, including well-traveled yachtsmen Bernard Moitessier and Robin Knox-Johnston. Crowhurst’s journey was mired from the start, undone mostly by bad decisions that included building his own boat—which he didn’t have time to finish—and, more stupefying, lying about his progress to the extent that he ultimately chose to fake his circumnavigation. Crowhurst’s background may have been humble, but his story is mythic: He practically sold his family’s souls in order to get sponsored, which meant that if he failed, he’d be financially ruined—yet soldiering on would almost certainly lead Crowhurst not to a trophy but to his grave. The play-by-play of the race makes Deep Water effortlessly riveting—Crowhurst wasn’t the only entrant with problems—but thanks to the inclusion of the grainy 16-millimeter film and audio logs that the competitors kept, it’s also haunting. Interviews with people such as Crowhurst’s wife, Clare, various journalists, and Knox-Johnston don’t quite give anything away. But even if you don’t know the end of this adventure, their hindsight-is-20/20 commentary combines with scenes of Crowhurst’s genial if increasingly troubled face—as well as fierce widescreen shots of the ocean—to imbue Deep Water with a tone that, like the competitor’s eventual mind-set, is deeply unsettling.