Complex sentence: Wyoming is one of the least successful states especially during 1980's -1990's at Miss Teen USA, the most successful of these was in 1985, when Emily Ernst placed first runner-up to Kelly Hu of Hawaii.
Split into simpler sentences: Wyoming is one of the least successful states, especially during 1980s and 1990s, at Miss Teen USA. The most successful of these was in 1985, when Emily Ernst placed first runner-up to Kelly Hu of Hawaii.