1993: Richard Gere and Cindy Crawford This power couple was so hot that the rules were amended for the year of 1993 with 'Sexiest Couple' replacing 'Sexiest Man.'While their no longer together, Cindy is just as gorgeous now as she was then. More on Richard in 1999.
1995: Brad PittBrad Pitt has transitioned from 'pretty boy' to powerhouse man and is still and is still one of the most, if not THE most, sexiest men in Hollywood.
1996: Denzel Washington Age ain't nothing but a number for Denzel Washington who is looking just as hot as ever over a decade after his Sexiest Man cover.
1997: George Clooney George Clooney successfully made the leap from TV star to Oscar-winning movie star in the years following this cover. Fortunately for ladies everywhere, he's still gorgeous and still an eternal bachelor.
1999: Richard GereThe other half of 1993's Sexiest Couple got to enjoy the spotlight solo in 1999. Today, Richard Gere is still looking good, although he can't quite hold a candle to Cindy anymore.