| 9th Annual Gotham Film Awards (1999) |
| Film |
| Breakthrough Actor |
| Dylan Baker - Happiness (TIE) | |
| Janet McTeer - Tumbleweeds (TIE) |
| Breakthrough Director (Open Palm Award) |
| David Riker - The City | |
| Tim Kirkman - Dear Jesse | |
| Eric Mendelsohn - Judy Berlin | |
| Mark Polish and Michael Polish - Twin Falls Idaho | |
| Frank Whaley - Joe the King |
| Special Awards |
| Classical Film Tribute |
| Klute |
| Below-the-Line Award |
| Carter Burwell |
| Producer/Industry Executive Award |
| Christine Vachon |
| Career Tribute |
| Meryl Streep |