There are two kinds of people in this world: Those who know Patrick Dempsey as the African-anteater-dancing, extra-anchovy-pizza-delivering nerd from his '80s movies, and those who know him as TV's sexy Dr. Derek Shepherd from Grey's Anatomy and other appearances in the aughts. Kids these days (if one can say that at 33) may find it hard to believe that the Patrick some of us remember from "Can't Buy Me Love" and "Loverboy" was ever less than dreamy. Yet the second biggest thing to ever come out of Lewiston, Maine (it will always be tough to supplant Muhammad Ali vs. Sonny Liston, part II) has made a true transformation from totally geek to totally chic.
His metamorphosis went slowly; a rather lean '90s (Ava's Magical Adventure and Bloodknot) gave way to a part in "Scream 3" in 2000. His career picked up steam with repeat parts in "Will & Grace" and as Reese Witherspoon's fiance in "Sweet Home Alabama." Then, of course, there is Dr. Shepherd.
Not only has his career regained its luster, his look has also, uh, improved. (Doesn't the visage on the right seem a bit more... aerodynamic?)
This made me wonder: What are the best geek-to-chic switchovers from the '80s to today? One contender must be Jerry O'Connell, who has certainly hit his stride in his career, as Detective Woody Hoyt in "Crossing Jordan," and in his personal life, where he is engaged to Rebecca Romijn. All of this is a far cry from his debut as pudgy Verne Tessio in the 1986 classic "Stand by Me." (Side note: Life must be tough when, after a grueling day of working with Jill Hennessy, you are forced to go home to Rebecca.)
As Carrie Bradshaw in the juggernaut "Sex and the City," Sarah Jessica Parker was both beautiful and sophisticated. Again, a far cry from an early career, this time as brainy and bespectacled Patty Greene in the early eighties sitcom "Square Pegs."
And whither Doogie Howser?
There are plenty more. Weigh in on your favorites in our reader poll and add comments describing those I may have missed. Extra credit will be given for extreme snarkiness, aimed at either celebs who have become chic, or your author, who has not.
When not guest-blogging, Michael Corones is an Opinions Producer at washingtonpost.com. Although he thinks of himself as tough and ruthless, in reality he looks closer to rough and toothless.
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