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On June 7, 2007, a group of Oregon State University women's studies students created a poster celebrating Underwood's selection as Playboy's 2007 Playmate of the Year, and posted it outside Bexel Hall, where it remained in place for only a few hours before Oregon State University staff took it down.

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The poster read, "Sara Jean: First OSU Beaver Playmate of the Year, Playboy June '07, OSU Centerfold, People, Ideas, Innovation." Underwood appears as a pirate wench in the 2007 film Epic Movie, along with fellow Playmates Qiana Chase, Irina Voronina and Jillian Grace.

Underwood appeared as a playmate in the 2008 comedy, House Bunny, along with fellow playmates and in 2009 was in the film The Telling with Bridget Marquardt and Holly Madison, and as herself in Miss March. In 2011, she was a substitute host and one of the regular presenters of "The Feed". She won her first stage heat after gaining a big lead on three Japanese contestants that had more pedigreed backgrounds in athletics.

She studied at Oregon State University and Portland State University.

She first worked as the assistant in sales of heavy construction equipment.

On Thursday morning (August 10, 2017) the American Sun-Times reported Sara Jean Underwood and boyfriend, to be shopping for engagement rings.