17 Weirdest Celebrity Couples of All Time

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When Kim Kardashian and Kanye West got together, we gave them our best side-eye, but it didn't seem that far-fetched that people so in love with themselves and attention would gravitate toward each other.

Not so with some of the other big couples in Hollywood, particularly those of the May-December varieties where the age gap is so great one could be the other's parent.

Then there are those pairings that inspire the public collectively asking "what could they POSSIBLY have in common?" Besides fame, that is. (And likely an affinity for kink.)

Some of Hollywood's best and brightest change significant others like normal people change underwear, so it's no surprise that some couplings are pretty bizarre.

Nevertheless, here are 17 weird celebrity couples we can't even believe:

Macaulay Culkin and Mila Kunis
Before becoming Ashton Kutcher's Baby Mama, Mila Kunis dated Macaulay Culkin...for EIGHT YEARS. Speaking of Ashton...

And speaking of those (sometimes) fleeting May-December romances, check out our gallery of some celebrity couples with big age differences between them.

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Miley Cyrus Biography

Miley Cyrus Hair Miley Cyrus has evolved tremendously over the years. Initially known for portraying Hannah Montana, the singer/actress made an effort to... More »
Born
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Franklin, Tennessee
Full Name
Destiny Hope Cyrus

Miley Cyrus Quotes

Thank you guys for all your support. Without you, none of this would be possible. I love every one of you and I could not be more appreciative. God bless you.

Miley Cyrus [at a concert, soon after photo scandal broke]

I have let myself down. I will learn from my mistakes and trust my support team. My family and my faith will guide me through my life's journey.

Miley Cyrus [on lewd photos]
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