16. Lina Lamont (Singin' In the Rain)
Singin' in the Rain's villain is Lina Lamont, the Hollywood starlet with a face of beauty and the voice of... well, no word can describe it other than Lamontesque. On the precipice of a career drop-off due to the development of talking pictures, Lamont finds herself at a crossroads both in her career and in her relationship with her leading man. Feeling betrayed by Don Lockwood for doting his attention on Kathy Selden, Lamont goes to extreme measures to ensure Kathy won't have a career in movies, despite being cute, charming, and having the vocal chops to dub over Lina's voice in their upcoming film. Lina also threats to sue the studio if it's ever leaked that the vocal work was done by Kathy, and even goes as far to essentially enslave her into continuing to do future dubbing for her.
Why We Can't Help But Love Her: Lina is so wonderfully stupid and unaware of the way she comes off that it verges on charming. Her delivery of the line "and I can't stannim" is enough to solidify her spot on this list.