| Answer | Crossword Clue |
|---|---|
| FOSSE | Best Musical of 1999 |
| FOSSE | Tony winner for Best Musical of 1999 |
| AMERICANBEAUTY | Best Picture of 1999 |
| SWANK | Best Actress of 1999 |
| CAINE | Best Supporting Actor of 1999 |
| JOLIE | Best Supporting Actress of 1999 |
| SWANK | Best Actress winner of 1999 |
| SPEARS | Billboard's Best New Artist of 1999 |
| CAINE | Best Supporting Actor of 1986 and 1999 |
| REAGAN | Subject of the 1999 best seller "Dutch" |
| LIFEISBEAUTIFUL | Winner of the 1999 Best Foreign Language Film Oscar |
| HARPERLEE | Alabaman who wrote the Best Novel of the Century, according to a 1999 Library Journal poll |
