Question: who won sexiest man alive more than once
Answer: 27 000000001989 - 12 - 16 - 0000 December 16 , 1989 Sean Connery 59 000000001990 - 07 - 23 - 0000 July 23 , 1990 Tom Cruise 28 000000001991 - 07 - 22 - 0000 July 22 , 1991 Patrick Swayze 38 000000001992 - 03 - 16 - 0000 March 16 , 1992 Nick Nolte 51 000000001993 - 10 - 19 - 0000 October 19 , 1993 Richard Gere ( 1 ) and Cindy Crawford ( Sexiest Couple Alive ) 44 ( awarded on 000000002015 - 11 - 18 - 0000 November 18 , 2015 ) Keanu Reeves 30 ( at the time ) 000000001995 - 01 - 30 - 0000 January 30 , 1995 Brad Pitt ( 1 ) 31 000000001996 - 07 - 29 - 0000 July 29 , 1996 Denzel Washington 41 000000001997 - 11 - 17 - 0000 November 17 , 1997 George Clooney ( 1 ) 36 000000001998 - 11 - 16 - 0000 November 16 , 1998 Harrison Ford 56 000000001999 - 11 - 15 - 0000 November 15 , 1999 Richard Gere ( 2 ) 50 000000002000 - 11 - 13 - 0000 November 13 , 2000 Brad Pitt ( 2 ) 36 000000002001 - 11 - 26 - 0000 November 26 , 2001 Pierce Brosnan 48 000000002002 - 12 - 02 - 0000 December 2 , 2002 Ben Affleck 30 000000002003 - 12 - 01 - 0000