There is actually a three way tie for the record of being named People Magazine's Sexiest Man Alive.
Johnny Depp (born John Christopher Depp II on June 9, 1963 in Owensboro, Kentucky) won the honor in 2009 and 2003.
Brad Pitt (born William Bradley Pitt on December 18, 1963 in Shawnee, Oklahoma) took the title in 1995 and 2000.
George Clooney (born May 6, 1961, in Lexington, Kentucky) held the honor in both 1997 as well as 2006.
There is also a possible fourth winner, Richard Gere (born Richard Tiffany Gere on August 31, 1949 in Philadelphia, Pennsylvania). In 1999 Gere won the title, after having held it (sort of) in 1993. The debate occurs because in 1993 he along with his wife Cindy Crawford were named Sexiest Couple of the Year, so some argue that Gere's first win doesn't count.