| 301 | 1996 | Cuba Gooding, Jr. - Jerry Maguire - "Rod Tidwell" |
| 302 | 1996 | William H. Macy - Fargo - "Jerry Lundegaard" |
| 303 | 1996 | Armin Mueller-Stahl - Shine - Peter Helfgott |
| 304 | 1996 | Edward Norton - Primal Fear - "Aaron Stampler" |
| 305 | 1996 | James Woods - Ghosts of Mississippi - Byron De La Beckwith |
| 306 | 1997 | Robin Williams - Good Will Hunting - "Sean Maguire" |
| 307 | 1997 | Robert Forster - Jackie Brown - "Max Cherry" |
| 308 | 1997 | Anthony Hopkins - Amistad - John Quincy Adams |
| 309 | 1997 | Greg Kinnear - As Good as It Gets - "Simon Bishop" |
| 310 | 1997 | Burt Reynolds - Boogie Nights - "Jack Horner" |
| 311 | 1998 | James Coburn - Affliction - "Glen Whitehouse" |
| 312 | 1998 | Robert Duvall - A Civil Action - "Jerome Facher" |
| 313 | 1998 | Ed Harris - The Truman Show - "Christof" |
| 314 | 1998 | Geoffrey Rush - Shakespeare in Love - Philip Henslowe |
| 315 | 1998 | Billy Bob Thornton - A Simple Plan - "Jacob Mitchell" |
| 316 | 1999 | Michael Caine - The Cider House Rules - "Dr. Wilbur Larch" |
| 317 | 1999 | Tom Cruise - Magnolia - "Frank 'T.J.' Mackey" |
| 318 | 1999 | Michael Clarke Duncan - The Green Mile - "John Coffey" |
| 319 | 1999 | Jude Law - The Talented Mr. Ripley - "Dickie Greenleaf" |
| 320 | 1999 | Haley Joel Osment - The Sixth Sense - "Cole Sear" |
| 321 | 2000 | Benicio del Toro - Traffic - "Javier Rodriguez" |
| 322 | 2000 | Jeff Bridges - The Contender - "President Jackson Evans" |
| 323 | 2000 | Willem Dafoe - Shadow of the Vampire - Max Schreck |
| 324 | 2000 | Albert Finney - Erin Brockovich - Edward L. Masry |
| 325 | 2000 | Joaquin Phoenix - Gladiator - "Commodus" |
| 326 | 2001 | Jim Broadbent - Iris - John Bayley |
| 327 | 2001 | Ethan Hawke - Training Day - "Jake Hoyt" |
| 328 | 2001 | Ben Kingsley - Sexy Beast - "Don Logan" |
| 329 | 2001 | Ian McKellen - The Lord of the Rings: The Fellowship of the Ring - "Gandalf" |
| 330 | 2001 | Jon Voight - Ali - Howard Cosell |