5
He Tried To Gaslight Salma Hayek Into Dating Him
When Trump wanted to date famous women, he'd simply masquerade as his own publicist and talk to the tabloids in great, breathy detail about how they wanted to jump his bones. He did this about everyone from Carla Bruni to Madonna to Kim Basinger. If you're going to be a creepy obsessive, you might as well shoot for the moon. But don't take our word for it. Just ask Salma Hayek, who once had the POTUS sliding real hard into her IRL DMs (that's what millennials call phones these days, according to our cool nephew who's totally not messing with us).
As Hayek described in an interview with Trevor Noah, it all kicked off after Trump noticed that she was looking a little cold at an event the two were attending (alongside her boyfriend). Trump gave Hayek his jacket and got to talking, an encounter that ended with him and the couple exchanging numbers and a promise to stay in touch. He never contacted the boyfriend, but oh boy did he stay in touch with Hayek.
"Now he's calling and he's inviting me out and it's just me. And I said, 'What about my boyfriend? Am I crazy, are you asking me out? You know I have a boyfriend.' He said, 'He's not good enough for you. Not important. He's not important, he's not big enough for you. You have to go out with me.'"
Despite Hayek repeatedly shutting down his advances, Trump, that yuge respecter of women's boundaries, kept calling and calling, until one day Hayek noticed a story in The National Enquirer about how a certain "genius" "billionaire" "playboy" "philanthropist" wouldn't date her because she was too short. And right on cue, Trump was on the horn offering up a way to prove this story was bull.
"He called and left me a message. 'Can you believe this? Who would say this? I don't want people to think this about you.' He thought that I would try to go out with him so people wouldn't think that's why he wouldn't go out with me."
As abhorrent as this might be, we have to ask: What if he tried this tack in negotiations with North Korea? Hayek was too smart for it, but Kim Jong-un ...
4
He Screwed Over A Hair Metal Band For "Charity"
Back in 1991, Trump was tapped by Precious Metal, an all-girl hair metal band, to appear in a video for their cover of "Mr. Big Stuff," the song originally made famous by Jean Knight. In return, the band agreed to donate $25,000 to a charity of his choice. Which was almost definitely guaranteed to be the Donald Trump Foundation for Self-Enrichment, or "Trump Foundation" for short (as cynical as that might sound).
Against all odds, Trump turned up to the shoot and did what he said he would. Which suggests that if we filled the Oval Office with wigs, smoke machines, and scantily clad ladies, he might get some work done. Anyway, afterward, Trump turned to the band and demanded that instead of $25,000, he be paid a whopping $250,000, his rationale being that he only signed on for a cameo, not to appear throughout the video.