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1987
Stepping out at the Mood premiere in Hollywood at the Mann's Chinese Theatre in Hollywood, a much younger, fresh-faced Dempsey wore a classic tuxedo and was clean shaven for the event.
1990
Dempsey stepped out with his hair slicked-back for press events surrounding the handful of TV and movie roles he was involved with at the time.
1995
More hair experimentation, this time in the shape of curly locks and a goatee. "I hate shaving," admits the Maine native.
1996
Of his hair, Dempsey says, "Whatever I can do to make it less painful for me to deal with is good." Here it is cropped again.
2002
He adopts a clean-cut look to play a mayor's son who woos Reese Witherspoon (and audiences) in Sweet Home Alabama.
2008
"My face is full of imperfections and it is what it is," Dempsey, who's landed gigs as the face of both Versace and Avon campaigns this year, says.
2009
The actor attended the 66th Annual Golden Globe Awards held at the Beverly Hilton Hotel with his hair coiffed just so.
2010
Dempsey arrived with shorter hair and a clean shaven face at the Ferrari 458 Italia North American celebrity auction to benefit Haiti at Fleur de Lys.
2011
Dempsey combed his 'do into a flattering style for the Transformers: Dark Side Of The Moon premiere in New York City.
2012
The actor looked handsome as ever while attending the McLaren Beverly Hills Grand Opening in Beverly Hills.
2013
The actor's look was on-point while attending The Petersen Museum's Race, Rock 'N Rally Gala in Los Angeles.
2014
Dempsey keeps looking better with time. The actor looked extra sharp while attending the Porsche Design Celebrates Festival of Watches in Beverly Hills.
2015
Dempsey looked absolutely dapper while at the Spectre premiere at Royal Albert Hall in London.
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