Question: who was named sexiest man alive the most times
Answer: 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 December 1 , 2003 Johnny Depp ( 1 ) 40 000000002004 - 11 - 29 - 0000 November 29 , 2004 Jude Law 31 000000002005 - 11 - 28 - 0000 November 28 , 2005 Matthew McConaughey 36 000000002006 - 11 - 27 - 0000 November 27 , 2006 George Clooney ( 2 ) 45 000000002007 - 11 - 26 - 0000 Novemb