Sherwood has held the titles of Miss Idaho Teen USA and Miss Idaho USA. At the age of 18, Sherwood was crowned Miss Teen USA 1989 and in 1997, first runner up Miss USA. Sherwood assumed the Miss USA crown when Brook Mahealani Lee was crowned Miss Universe 1997 in Miami. To date, Sherwood is the first and so far the only person to have held the titles of both Miss Teen USA and Miss USA.
In 1996, Sherwood was invited on a modeling trip with six other women to Brunei by her friend, former Miss USA Shannon Marketic. When Marketic alleged in a lawsuit against the ruling family of Brunei that they were raped and forced into sexual slavery, Sherwood first supported her lawsuit but then distanced herself from it when she became Miss USA. The lawsuit was thrown out because of the royal family's immunity as heads of state.
Sherwood is currently a model on the long running game show The Price Is Right. She also has acted in a few recent movies including "Shark Zone", released in 2003.
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