Robin Wright and Naomi Watts star as two mothers who fall for each other's sons in Anne Fontaine's taboo sex drama, Adore, out Sept. 6.
Coining the phrase "M.I.L.F.," American Pie introduced audiences to Stifler's mom -- played to perfection by Jennifer Coolidge -- who engages in a sexual relationship with her son's high school pal Finch (Eddie Kaye Thomas). The classic teen comedy was released in 1999.
In the 2009 drama, Michelle Pfeiffer plays Lea, a retired courtesan who has a six-year affair with 19-year-old Chéri (Rupert Friend). When Chéri's mother (Kathy Bates) arranges a marriage for her son to the daughter of another courtesan, the two must decide if they are truly in love.
In the 2011 comedy film starring Owen Wilson, Jason Sudeikis, Christina Applegate and Jenna Fischer, two fed-up wives give their husbands a "hall pass" -- a week off marriage to do whatever they want without any consequences. But the guys aren't the only ones that take advantage of the break. Teen Wolf's Tyler Hoechlin, playing a college baseball player, finds himself courting Applegate's married character.
'Notes on a Scandal'
A riveting story of deceit, loneliness and manipulation, the 2006 British psychological thriller tells the story of a bitter veteran teacher (Judi Dench) who finds out that her high school's new art teacher (Cate Blanchett) is having an affair with her 15-year-old student.
Fifteen-year-old Oscar (Aaron Stanford) falls in love with his stepmother (Sigourney Weaver), certain that he is a better match for her than his work-obsessed father, in Tadpole. The 2000 romantic comedy was directed by Gary Winick.
The classic 1967 film tells the story of a recent college graduate (Dustin Hoffman) embroiled in an affair with Mrs. Robinson (Anne Bancroft), the seductive wife of his father's business partner.
Taking place in postwar Germany, Michael Berg (Ralph Fiennes) re-encounters Hanna Schmitz (Kate Winslet) eight years after their affair -- one that mysteriously ended when he was 15 and she was 36.
Catherine Zeta-Jones stars as Sandy, a housewife and mother of two who moves to New York City after discovering her husband's infidelity in this 2009 rom-com. She is enticed by her 25-year-old, kid-loving neighbor (Justin Bartha), who eventually becomes much more than her full-time nanny.
Jane Seymour is a scene stealer in 2005's Wedding Crashers, as she attempts to lure Owen Wilson's character to her bedroom. Vaughn, meanwhile, has his sights set on Seymour's daughter, played by Isla Fisher.