Berry graduated from Bedford High School where she was a cheerleader, honor student, editor of the school newspaper and prom queen. She worked in the children's department at Higbee's Department store. She then studied at Cuyahoga Community College. In the 1980s, she entered several beauty contests, winning Miss Teen All American in 1985 and Miss Ohio USA in 1986. She was the 1986 Miss USA first runner-up to Christy Fichtner of Texas. In the Miss USA 1986 pageant interview competition, she said she hoped to become an entertainer or to have something to do with the media. Her interview was awarded the highest score by the judges. She was the first African-American Miss World entrant in 1986, where she finished sixth and Trinidad and Tobago's Giselle Laronde was crowned Miss World. According to the Current Biography Yearbook, Berry ". . . pursued a modeling career in Chicago. . . . Berry's first weeks in New York were less than auspicious: She slept in a homeless shelter and then in a YMCA".
“When you’re looking for certain things, host of a game show is very different," 500 Questions producer and reality heavyweight Mike Darnell tells The Hollywood Reporter during the Reality Roundtable. Darnell breaks down the different aspects he looks for when casting his shows, between a host, a judge and a contestant.