One of a TV fan’s favorite pastimes is to look into the histories of the actors that play their favorite characters. What shows were they on before? Were there any scandals? How badly did they have to embarrass themselves before they landed a decent gig?

One actor who requires no searching is Patrick Dempsey, who plays Dr. Derek Shepherd on Grey’s Anatomy. Who could ever forget his best role ever, the quintessential nerd in the 1987 flick Can’t Buy Me Love?

Dempsey played Ronald Miller, a sweet and intelligent 17-year-old who desperately longs for popularity. So he comes up with a scheme…to pay the most popular girl in school 1,000 dollars to pretend to like him. Aww…heart-breaking isn’t it? Just wait until you see the film. If you haven’t, go here for more details: it’s something you cannot miss.

The character of Ronald Miller was so beloved, in fact, that many fans can never forget him in the role. Which is why Dempsey’s smooth confidence on Grey’s Anatomy often seems wrong, somehow. America loves a nerd, so it’s no surprise that Grey’s adorably rumpled T.R. Knight, who plays Dr. George O’Malley, is the breakout heartthrob of the show. Maybe Dempsey should consider returning to his roots…