'70s <--- '80s <--- 1990 | 1991 | 1992 | 1993 | 1994 | 1995 | 1996 | 1997 | 1998 | 1999

1999

Issue #339 | January 1999

Issue #340 | February 1999

Issue #341 | March 1999 | Rebecca Seidel

Issue #342 | April 1999 | Cassidy Light

Issue #343 | May 1999 | Michelle Williams

Issue #344 | June 1999

Issue #345 | July 1999

Issue #346 | August 1999 | Natalie Portman

Issue #347 | September 1999 | Britney Spears

Issue #348 | October 1999 | Sarah Michelle Gellar

Issue #349 | November 1999

Issue #350 | December 1999 | Katie Holmes