Shady Love: The Creepiest Celebrity Couples Of All-Time

- By Bossip Staff
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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.

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    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.

    Jerry Seinfeld and Shoshanna Lonstein

    Yea, this really happened. Creeepy.

    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?

    Mary-Kate Olsen & Olivier Sarkozy

    The photo pretty much sums up their creepy relationship.

    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.

    Aaron Taylor-Johnson and Sam Taylor-Wood

    The popular actor (24) and his director wife (47) have ignored the haters, found true happiness and started a family which never seems to take the focus off their eyebrow-raising age difference.


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