'Cal' Hockley, 'Titanic' (1997)
Immortally portrayed by Billy Zane, Caledon "Cal" Hockley is the heir to a Pittsburgh steel fortune — part businessman, part high school quarterback, and stiffer than Trump's immigration policies all the way through. He has a nasty habit of losing the things most precious to him because of his wanton indifference towards the women of the world, whom he sees only for what they have to offer him. (Draw your own conclusions.)
And like Trump, who sold his yacht (the endearingly named "Trump Princess") in 1991 when he hit financial straits, Hockley never had much luck with boats. "You can be blasé about some things, Rose," he mansplains to his fiancée, "but not about Titanic. It's over one hundred feet longer than the Mauritania and far more luxurious." We get it: It's huge. It's the greatest ship of all time. Everyone who's not on this unsinkable floating palace is a loser!