In honor of our 25th anniversary, we take a look back at 1999's dreamy awards season style ... Will Smith & Jada Pinkett 41st Annual GRAMMY Awards; PHOTO BY KMAZUR Jane Leeves 56th Annual Golden ...

Lauryn Hill was the first hip-hop artist to win five awards at a Grammy ceremony. She achieved the feat in 1999, though none were in rap categories. She won album of the year and best R&B album ...

Santana, the 52-year-old singer-guitarist who played at the original Woodstock in 1969, took home eight Grammys for his 1999 ... a Grammy for song of the year. Santana, meantime, won awards ...