10 Most Unexpectedly Depressing Movies

To take a cursory glance at The Last American Virgin, you'd assume that it was your typical '80s boner comedy that didn't have much to offer beyond some basic titillation, skeevy jokes, and a predictable ending where the nerdy guy gets the girl, right?

Except, filmmaker Boaz Davidson clearly had no interest in delivering a fully down-the-line sex comedy, and instead swerved audiences completely.

Throughout the film, high-schooler Gary (Lawrence Monoson) desperately pursues the beautiful, virginal Karen (Diane Franklin), who ends up having sex with Gary's misogynistic pal Rick (Steve Antin).

Karen falls pregnant and is subsequently dumped by an indifferent Rick, at which point Gary helps Karen pay for an abortion by selling most of his belongings and borrowing money from his boss.

Karen and Gary appear to grow closer over the following days: they share a kiss, and Karen invites Gary to her 18th birthday party. But when an excited Gary turns up, she walk in on Karen making out with Rick, before leaving the party distraught and driving home in tears. The End.

It's an insanely harsh and yet totally realistic outcome to Gary's quest: Karen returned to the hot ladies' man and, despite his nice guy efforts, Gary just didn't do it for her. You can't make someone love you, no matter how good you are to them.

Given that the story seemed perfectly on-track for Gary to get the girl and his happily ever after, this was a brutal resolution, and with the abrupt transition to the end credits afterwards, there's no attempt at all to cushion the heartbreak.