Miss USA 1999

Miss USA 1999 was the 48th Miss USA pageant, held at the Grande Palace Theatre in Branson, Missouri on February 4, 1999. Kimberly Pressler became the fourth former Miss Teen USA state delegate in five years to win or inherit the Miss USA title.

At the conclusion of the final competition, Kimberly Pressler of New York, was crowned by outgoing titleholder Shawnae Jebbia of Massachusetts. Pressler became the fourth titleholder from New York, following Shanna Moakler four years prior as Miss USA 1995. However, as Moakler inherited the crown after Chelsi Smith won Miss Universe 1995, this is the third outright win for New York, and the first in twenty years since Mary Therese Friel won Miss USA 1979.

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 to 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.