Jewel Kilcher in Ride with the Devil (1999)

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Set in southern Missouri, Ang Lee's Civil War Epic Ride with the Devil (1999) follows the bloody skirmishes between Jayhawkers (Union soldiers) and Bushwackers (guerillas fighting for the Confederate cause) that followed the slave-holding state's decision to fight with the Union. Along with an accurate portrayal of the period, this movie also gives us a peek at Jewel's top-boob as she breast-feeds her baby.