Q: There's an old movie starring Patrick Dempsey as a teenaged pizza delivery boy -- what was it called?

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Adam Thomlison / TV Media

The film you're looking for is the surprisingly PG-13-rated "Loverboy" (1989). It features Patrick Dempsey, known today as Dr. McDreamy on "Grey's Anatomy," who even then was leveraging his good looks to play a young pizza delivery boy and, for some select clients, prostitute.

That's the sort of premise that could easily be treated seriously or not, but it's an unlikely one to be treated to a PG-13 rating. The trick, according to "New York Times" reviewer Caryn James, was to make all the sex scenes decidedly unsexy.

Director Joan Micklin Silver "directs 'Loverboy' as if [Dempsey's character] Randy really were delivering pizza. It is that unexciting, that nonsexual, that reluctant to admit that Randy's life is a little more lurid than the average college kid's."

The story is predictably unlikely, the way all good teen-fantasy comedies were in the '80s. Dempsey's character is seduced by an older woman on his pizza route, who offers to help him pay for college. She tells her other lonely, attractive friends about him, and an order for pizza with "extra anchovies" becomes code for pizza with paid-for sex. But, of course, he keeps this side business a secret from his wholesome girlfriend and his family until it all starts to unravel.

This film came in the brief sweet spot of Dempsey's career, when he was a sought-after leading man and big-screen heartthrob. One of the best-remembered films of this period was actually a sort of reversal of the "Loverboy" setup: in the 1987 teen comedy "Can't Buy Me Love," Dempsey plays a high school outcast who pays a popular girl to be his girlfriend.

However, that was an almost less-likely scenario, and so the majority of his films at the time featured the smirking, chiseled-looking Dempsey being chased after by multiple attractive women.


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