Mere weeks after Diana's tragic death, NBC's Stone Phillips asked Trump if he could have dated her, to which he replied, "I think so, yeah. I always have a shot." Yeah, in case you didn't know, it's the job of the fourth estate to figure out which celebrities had the best chance of fucking recently deceased dignitaries.

Not letting the matter drop, months later, Trump said, "I only have one regret in the women department -- that I never had the opportunity to court Lady Diana Spencer." Which may be evidence that Trump purchases his women from some sort of department. And when asked by Howard Stern the same year Diana died if he "could've nailed her," Trump responded: "What an appalling question! I won't dignify such thoughtless vulgarity with an answer."

Kidding. He said: "I think I could have."

People

This wasn't Trump's only celebrity crush, either. According to Salma Hayek, he asked her out, and when she refused, an unflattering article showed up in the tabloids, which she suspects may have planted by Trump to use as leverage to get that date. Which is so messed up that it wouldn't surprise us if this incident isn't where the whole "wall" idea stemmed from.

Of course, few people with amusement park rides on their property aren't super eccentric, but one story of Jackson's fandom is particularly off-putting. For those who weren't reading tabloids in the late '70s, Jackson briefly dated JFK's daughter Caroline Kennedy -- not because he was genuinely interested in cultivating a relationship with her, but because he was hoping to score an introduction to her mom.

It seems that Jackson became obsessed with former first lady Jackie Onassis after being given a nude paparazzi photo of her as a gift. He told his sister, "I just can't stop looking at it ... I must meet her." While maybe a 13-year-old boy who found a Playboy in the woods and decided to run away from home to live at the Playboy Mansion can sympathize with his conclusion, things got decidedly weirder.

Jackson befriended Caroline and began calling her incessantly, "hoping that maybe Jackie would answer." Caroline eventually agreed to go out with him, which didn't exactly go well. At the end of the date, Caroline shot down Michael's advances because she claimed her mother would kill her for kissing a black boy, sending him home in tears. Michael eventually did meet Jackie, though.

Doubleday

But it came about not through some sort of wacky scheme, but because she edited his memoir. She also refuted her daughter's claims that she was a racist, meaning that she probably made that up to avoid making out with the weirdo who was fixated on her naked mom.

Since Carrey peppered in references to how old he is, the whole thing was probably a joke -- you know, like the kind of hilarious jokes older men make to waitresses after three or four gin and tonics. The whole thing also seemed to be in the service of promoting Carrey's streaming video website, which presumably consisted of more cringeworthy mid-life crisis confessions and clips from Mr. Popper's Penguins. When asked if it was a joke on Twitter, Carrey actually made things more convoluted:

Twitter

Adding to fuel to the already raging fire of creepiness, Stone herself didn't know what the hell all this was about, posting "Should I be flattered or seek an order of protection?" on her YouTube account. Maybe Carrey was right in the '90s when demanding that somebody stop him.

But there was a time when Dylan was nothing but some scruffy young kid on the road to greatness. So how did he launch his career? By stalking his idol, folk legend Woody Guthrie. According to the Dylan biography Down The Highway, when Dylan first came to New York, he headed straight to Guthrie's home. Unfortunately, Guthrie was already living in a health facility, and his wife wasn't home, but Dylan did manage to terrify two small children and piss off a 16-year-old babysitter.

Bettmann/Getty Images

After knocking on the door and being turned away several times, Dylan finally dropped the bomb that he had "no place to stay" -- so he was looking to meet his musical hero and find a place to crash for the night. Dylan's memoir tells a slightly different version, insisting that he'd already befriended Guthrie in the hospital and was disturbing his family in the hopes of finding some of his unused song lyrics.

Even after he became the Dylan we all know and love, he's had a weird relationship with celebrity fandom. He once randomly popped by Neil Young's childhood home for a tour, to the complete surprise of the Winnipeg family who lives there now. (Dylan's got a thing for wandering around total strangers' property.) And in recent albums, he's randomly dropped references to Leonardo DiCaprio in Titanic and mentioned crying at the thought of Alicia Keys' childhood, despite the fact that he's never met her -- probably because Dylan's musical inspirations these days are limited to what happens to be on cable that day.

According to Stamp, he agreed to do The Phantom Menace because of pressure from his agent, but mainly because he "had a terrible crush on Natalie Portman" -- "terrible" being a pretty good descriptor, because at the time of filming, Stamp was around 60, and Portman hadn't turned 18 yet. He was also a big fan of Leon: The Professional, which is itself a not-quite-kosher story of an old man befriending a minor (and which was almost way worse).

Gaumont

After traveling "halfway around the world" to meet her, Stamp showed up for his scenes with Portman and found her missing. According to Stamp: "I said, 'Where's Natalie?' And George says, 'That's Natalie,' and points to a bit of paper on the wall." And perhaps after a moment of thinking that George Lucas had Beauty And The Beast-ed his cast into sentient everyday objects, Stamp realized that he was going to blue screen the whole goddamn movie.

So yeah, The Phantom Menace's candy-colored sirocco of CG crap might've ruined your childhood, but at least it spared Portman several hours of hanging out with the unabashedly creeping "President of the Universe" (which, by the by, is how Stamp summed up that random-ass dude he played).

It's Spring Break! You know what that means! Hot coeds getting loose on the beaches of Cancun and becoming imperiled in all classic beach slasher ways: Man-eating shark, school of piranhas, James Franco with dreadlocks. There are so many films about vacations gone wrong, it's a chore to wonder if there's even such a thing as a movie vacation gone right. Amity Island and Camp Crystal Lake are out. So what does that leave? The ship from Wall-E? Hawaii with the Brady Bunch? A road trip with famous curmudgeon Chevy Chase? On this month's live podcast Jack O'Brien and the Cracked staff are joined by some special guest comedians to figure out what would be the best vacation to take in a fictional universe.

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