Creepiest Celebrity Couples Ever
For years, famous creeps have gallivanted around Hollyweird (aka Creepville, USA) with young eye candy and no major backlash. At times, there were loud whispers but never any major pressure to change a creepy culture that’s only grown worse (and more glamorous) over time.
Hit the flip for the creepiest celebrity couples of all-time.
R. Kelly and Aaliyah
Legendary sicko R. Kelly allegedly married budding R&B star Aaliyah when she was only 15 during the infamous “Age Ain’t Nothing but a Number” era. The self-proclaimed “Pied Piper” (No, that isn’t creepy) was 28 at the time and later denied the marriage but, seriously, would you really believe R. Kelly?
Tyga and Kylie Jenner
A 25-year-old rapper with a 3-year-old child frolicking around with a 17-year-old home school dropout? So many things wrong in one sentence.
Michael Jackson and Lisa Marie-Presley
Mike and Lisa were the ideal celebrity couple until “the cringe-worthy kiss” during the VMAs that left a bizarre taste in everyone’s mouth.
Big Sean and Ariana Grande
This “relationship” between star rapper and Pop starlet just feels wrong on multiple levels. Mostly because Ariana looks 12-years-old.
Billy Bob Thornton and Angelina Jolie
The “creepy step-father in love with his step-daughter”-dynamic never really won the public over.
Morgan Freeman and E’Dena Hines
So, there was that pesky rumor that the iconic actor married his step-granddaughter E’Dena Hines which they both vehemently denied despite endless media reports.
Anna Nicole Smith and J. Howard Marshall
In most cases, there’s only one reason why an eye-popping 26-year-old would marry an old, decrepit, shriveled up billionaire and it isn’t love. Luckily for Anna, the relationship only lasted 14-months before his death/her expected pay day.
Mike Will Made It and Miley Cyrus
The super-producer and Pop star never officially confirmed their relationship but, with pics like this scattered across the ‘net, they didn’t need to.
Woody Allen and Soon-Ye
Notorious creep Woody Allen dated his ex’s 19-year-old daughter when he was 56 before they eventually married in one of the creepest Hollyweird love stories ever.
Macaulay Culkin and Mila Kunis
At no point did this relationship seem normal (or healthy) and yet it went on (for years) despite the very peculiar vibe between the two.
Steven Bauer and Lyda Loudon
The 57-year-old “Ray Donovan” star and his 18-year-old girlfriend don’t seem to mind their relationship backlash because “the heart wants what it wants,” right?
Prince William & Kate Middleton
Something’s always been off about this royal marriage that’s very older brother-younger sister-ish.
Hayden Panettiere and Wladimir Klitschko
The 38-year-old heavyweight champ and his 25-year-old actress boo have this “high school gym teacher and student” thing going on. And yea, it’s kinda creepy.
Doug Hutchison and Courtney Stodden
The creepy actor famous for creepy roles married a 16-year-old at the tender age of 50 thus completing the trifecta of creepiness.