Winter oilseeds are cool season Brassica crops currently being grown in the upper Midwest and North-West of the United States. They have the potential to function as dual crops when grown in rotation with corn, soybean, and small grains. They provide many of the benefits of typical cover crops over winter, with the added benefit of extra revenue to growers who sell the seeds for uses such as biofuel, industrial products, human consumption, or animal feed. This review gathers current agronomic and industrial use information about canola (Brassica napus L.), camelina [Camelina sativa (L.) Crantz], and pennycress (Thlaspi arvense L.). Currently, most research involving these crops is specific to the Midwest. This review also poses questions regarding how these crops could be adapted to grow in the Mid-South, with further research being necessary in several areas before promoting adoption in the region.