22. Swept Away (2002)
Director: Guy Ritchie
Stars: Bruce Greenwood, Madonna, Elizabeth Banks, Jeanne Tripplehorn, Adriano Giannini
Lame Love Song: "Fade into You," Mazzy Star
Love Conquers: A shipwreck
Madonna is the iron woman of awful romantic comedies. Her relationship with Sean Penn precipitated the terrible Shanghai Surprise, but the equally atrocious Swept Away was a creative collaboration between herself and husband Guy Ritchie a decade and a half later.
You have to give the Material Girl credit for persistence. No matter how often the world tells her that she is never going to be a leading lady, she turns around and manipulates a beau into a career-damaging cinematic endeavor. All of this while employing a sterilization team to protect her DNA, practicing Kaballah, and sometimes singing! Quite, umm, impressive?!