Miss USA 1999, the 48th Miss USA pageant, was held at the Grande Palace Theatre in Branson, Missouri on February 4, 1999.
At the conclusion of the final competition, Kimberly Pressler of New York, was crowned by outgoing titleholder Shawnae Jebbia of Massachusetts. Pressler became the third Miss New York USA to win the crown on finals night, and the fourth titleholder from New York.
After months of negotiation, Branson was announced as the pageant's location in November 1998. City officials spent $125,000 of tax money to host the pageant in Branson in the hope that it would encourage tourism but admitted after the pageant that it was not worth the cost. Sponsors contributed a further $1 million towards the hosting of the event. The pageant had previously been held in Shreveport, Louisiana from 1997-1998.
Shemar Moore hosted the pageant for the only time, and color commentary was added by Miss USA 1996 Ali Landry and Julie Moran, for the second consecutive year. Entertainment was provided by Collin Raye and The Atomic Fireballs.
Miss Congeniality: Cara Jackson (Arizona)Miss Photogenic: Elyzabeth Pham (Wisconsin)Style Award: Kellie Lightbourn (Virginia)Best in Swimsuit: Lauren Poppell (South Carolina)The Miss USA 1999 delegates were:
This is the first time New York has held the Miss USA title in four years. Shanna Moakler, Miss New York USA 1995, inherited the Miss USA 1995 title, after Chelsi Smith won Miss Universe 1995. However, this is the first outright win for New York in 20 years, when Mary Therese Friel won Miss USA 1979.Kimberly Pressler became the fourth former Miss Teen USA state delegate in five years to win or inherit the Miss USA title.Tennessee made the top three for the third time in four years. At the time, High's 1st runner-up placement was the highest finish from a Tennessee delegate in Miss USA history. However, Tennessee went on to win Miss USA 2000 and Miss USA 2007.California made the top three for the second consecutive year.South Carolina placed for the first time since Lu Parker won Miss USA 1994. Lauren Poppell was also the first woman representing South Carolina to place at both Miss Teen USA (1993) and Miss USA (1999.)This was New Mexico's first placement since 1987.Ohio placed for the first time since 1990.Virginia placed in the Top 10 back-to-back for the first time since 1981-1982.Thirteen delegates had previously competed or would later compete in either the Miss World, Miss Teen USA or Miss America pageants.
Delegate who would later compete in Miss World:Angelique Breaux (California) - Miss World USA 2000 (Top 10 semifinalist at Miss World 2000)Delegates who had previously held a Miss Teen USA state title were:Kimberly Pressler (New York) - Miss New York Teen USA 1994Lauren Poppell (South Carolina) - Miss South Carolina Teen USA 1993 (Top 12 semifinalist at Miss Teen USA 1993)Meredith Young (Georgia) - Miss Georgia Teen USA 1991 (1st runner-up at Miss Teen USA 1991)Terri Bollinger (Missouri) - Miss Illinois Teen USA 1990Trini-Ann Kaopuiki (Hawaii) - Miss Hawaii Teen USA 1991Carissa Blair (Texas) - Miss Texas Teen USA 1992WyLynda Sipple (Nebraska) - Miss Michigan Teen USA 1992Amy Jo Ambrose (Idaho) - Miss Idaho Teen USA 1995Amanda Carraway (Kansas) - Miss Kansas Teen USA 1996Amanda Burns (West Virginia) - Miss West Virginia Teen USA 1997Delegates who had previously held a Miss America state title:Cara Jackson (Arizona) - Miss Arizona 1995Lori Menshouse (Kentucky) - Miss Kentucky 1997Dennis BassoJoyce BrothersKelly Le BrockCheech MarinMichelle PhillipsKevin RichardsonStuart Weitzman 
