Losing one's virginity can be a Herculean task in real life, and even more difficult in movies. Cinema has long depicted hapless men and women going to incredible lengths to join the ranks of the sexually active. There have been countless horny teens and one unforgettable 40-year-old virgin, but nobody like real-life poet, journalist, and polio patient Mark O’Brien.

In the indie drama The Sessions, John Hawkes portrays O'Brien, who is paralyzed from the neck down and dependent on an iron lung to breathe, but nonetheless strives to lose his virginity before he dies. He attempts to achieve this through the use of sex surrogate Cheryl Cohen Greene (Helen Hunt), who is hired to be his first. It’s an incredibly heartfelt and powerful look at the struggles of a man trying to come to terms with himself and his own disabilities.

Not all on-screen virgins' quests are as challenging or emotional as O'Brien's, but many are nonetheless impressive. To help prove that, and perhaps make a few struggling virgins' plight feel less like "mission: impossible," Complex counts down The 10 Most Memorable Plans to Lose Virginity in Movies.

RELATED: The 20 Most Gratuitous Girl-on-Girl Scenes in Movies
RELATED: The 20 Hottest Virgins in Movies and TV

RELATED: Hottest Car Sex Scenes

Written by Jason Serafino (@serafinoj1)