High Quality Content by WIKIPEDIA articles! The 41st Grammy Awards were held on February 24, 1999. They recognized accomplishments by musicians from the year 1998. Lauryn Hill was the nights big winner winning a total of 5 awards including Album of the Year and Best New Artist. Madonna won three awards while country musicians the Dixie Chicks, Vince Gill, Shania Twain won two apiece. Celine Dion also received two awards both for My Heart Will Go On, which received a total of four awards. It is widely remembered for Ricky Martin performance of "La Copa De La Vida"/ "The Cup of Life".