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| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | April | 1984 | | | | | | Daryl Hannah |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | March | 1985 |  |  |  |  |  | Jerry Hall |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | April | 1985 | | | | | | Kelly LeBrock |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | June | 1988 |  |  |  |  |  | Cybill Shepard |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | June | 1989 | | | | | | Kim Basinger |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | December | 1989 |  |  |  |  |  | Michael Jackson |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | April | 1991 | | | | | | Madonna |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | August | 1991 |  |  |  |  |  | Demi Moore |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | June | 1992 | | | | | | Annette Bening |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | August | 1992 |  |  |  |  |  | Demi Moore |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | January | 1993 | | | | | | Claudia Schiffer |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | August | 1993 |  |  |  |  |  | Cindy Crawford,K.D. Lang |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | October | 1993 | | | | | | Julia Roberts |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | May | 1994 |  |  |  |  |  | Jodie Foster |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | August | 1994 | | | | | | Cindy Crawford |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | November | 1994 |  |  |  |  |  | Barbra Streisand |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | January | 1995 | | | | | | Michael Douglas |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | April | 1995 |  |  |  |  |  | Jennifer Jason Leigh,Uma Thurman,Nicole Kidman,Patricia Arquette,Linda Florentino,Gwyneth Paltrow,Sarah Jessica Parker,Julianne Moore,Angela Bassett,Sandra Bullock |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | June | 1995 | | | | | | Courtney Love |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | July | 1995 |  |  |  |  |  | Nicole Kidman |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | August | 1995 | | | | | | Keanu Reeves |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | September | 1995 |  |  |  |  |  | Sandra Bullock |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | December | 1995 | | | | | | Friends Cast |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | January | 1996 |  |  |  |  |  | Uma Thurman |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | February | 1996 | | | | | | Emma Thompson |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | March | 1996 |  |  |  |  |  | Sharon Stone |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | April | 1996 | | | | | | Tim Roth,Leonardo DiCaprio,Matthew McConaughey,Benicio Del Toro,Michael Rapaport,Stephen Dorff,Johnathan Schaech,David Arquette,Will Smith,Skeet Ulrich |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | April | 1996 |  |  |  |  |  | Leonardo DiCaprio,Matthew McConaughey,Tim Roth,Benicio Del Toro,Michael Rapaport,Stephen Dorff,Johnathan Schaech,David Arquette,Will Smith,Skeet Ulrich |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | May | 1996 | | | | | | Alex Rousseau,Jenny Thompson,Dominique Moceanu,Nancy Reno,Nick Bravin,Tinker Juarez,Jon Brown,Sheila Hudson,Michael Johnson,Mark Henry,Rebecca Twigg |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | June | 1996 |  |  |  |  |  | Tom Cruise |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | July | 1996 | | | | | | Nicolas Cage |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | August | 1996 |  |  |  |  |  | Matthew McConaughey |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | September | 1996 | | | | | | Alicia Silverstone |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | October | 1996 |  |  |  |  |  | Anthony Hopkins |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | November | 1996 | | | | | | Madonna |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | December | 1996 |  |  |  |  |  | George Clooney |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | January | 1997 | | | | | | Goldie Hawn |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | March | 1997 |  |  |  |  |  | Julia Louis-Dreyfus |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | April | 1997 | | | | | | Cameron Diaz,Kate Winslet,Claire Danes |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | May | 1997 |  |  |  |  |  | Liv Tyler |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | July | 1997 | | | | | | Princess Diana |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | September | 1997 |  |  |  |  |  | Renee Zellweger |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | October | 1997 | | | | | | Nicole Kidman |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | November | 1997 |  |  |  |  |  | Bill Clinton,Al Gore |  |
| | | | | | | | |  | | | | | | | Vanity Fair Magazine | | | | | | | December | 1997 | | | | | | Matt Damon |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Vanity Fair Magazine |  |  |  |  |  |  | January | 1998 |  |  |  |  |  | Leonardo DiCaprio |  |