| 1999 Kansas City Film Critics Circle Awards |
| Best Film |
| American Beauty |
| Best Director |
|
Sam Mendes
American Beauty |
| Best Actor |
|
Kevin Spacey
American Beauty |
| Best Actress |
|
Reese Witherspoon
Election |
| Best Supporting Actor |
|
Haley Joel Osment
The Sixth Sense |
| Best Supporting Actress |
|
Catherine Keener
Being John Malkovich |
| Best Foreign Film |
| Run Lola Run |
| Best Documentary |
| Buena Vista Social Club |
| Best Animated Film |
| Toy Story 2 |