Before gracing our pages as both a Playmate in July 2006 and Playmate of the Year in 2007, Underwood was a marketing student at Oregon State. During that time, she posed for our Girls of the Pac-10 pictorial. “I had never done anything like that before,” she told Playboy. “I didn’t think that I was pretty enough.” 

Oh how wrong she was. Underwood made her debut in the October 2005 issue, nude wearing nothing but body paint (Oregon State colors) and holding a Bunny-branded football. The cover got a lot of attention, but most importantly, it got the attention of Hugh Hefner, who nominated Underwood to be Playmate of the Month. Readers voted her Playmate of the Year. Upon hearing the announcement, Underwood was dumbfounded. “One day I was a student, and the next I was Playmate of the Year,” she declared.

Since her revered pictorials in our pages, the small town beauty has taken to acting, with small roles in movies like House Bunny, Epic Movie, Miss March, The Telling, and was cast as the lead in the horror thriller Deadly Weekend. Underwood’s quest for stardom landed her on TV as well. She worked for the Blackbelt TV cable network and co-hosted five episodes of G4's Attack of the Show, filling in for fellow Playmate, Olivia Munn. Most notably, perhaps, was the steamy commercial Underwood shot for burger-chain Hardees with fellow knockout, Emily Ratajkowski. If you haven’t seen it, see it. 

When it comes to matters of love, Underwood prefers a low-maintenance man, listing show-offs, shaved chests and “guys who say what they think I want to hear,” as romantic dealbreakers. “I like the genuineness of shy guys,” Underwood mentions. “Girls can shave their legs and spend time thinking about what looks good, but I want a guy to just grab the first clothes he sees in the morning and be natural.”