10 Celebrities You Won't Believe Dated!

You'd think celebrities would have the pick of the litter when it came to dating

and that their options would be as endless as the fish in the sea. But still, our favorite actors, actresses, and artists often end up dating..

other celebrities. Let's take a look at the top 10 celebrities you won't believe actually dated

Welcome to Rankworthy, the show where we rank just about everything. Obviously, you know Culkin as one of the most successful child actors of all time

who segued into adult stardom thanks to films like Party Monster and Saved

Over the eight years they dated, Mila Kunis ascended from the 70s show to roles in major films like Jupiter Ascending, Bad Moms, and Black Swan

The fact that Mila Kunis and Macaulay Culkin dated for almost a decade may seem weird now, especially since Mila is happily married to the hunky Ashton Kutcher

But back in the early 2000s, they were one of Hollywood's it couples. Remember Adam Durant's? No? He's from the band Counting Crows. They did that song in Shrek

Well, he was a mainstay of the music scene in the mid-1990s

His cultural revelance has since waned, but at one point he was a highly recognizable individual

Duritz probably knew that his star wasn't going to last forever, so he took a swing while he was at bat

Who did he go after? Jennifer Aniston. Yeah, don't worry, you're not crazy. She was out of his league

But that didn't stop him from going for it. What's most shocking, though, is that Adam first dated Jen's co-star and friend, Courtney Cox

Bold move. Marilyn Manson has had some ups and downs over the course of his life He been addicted to heroin lost vast sums of money and had two long relationships end due to irreconcilable differences

He's a performer known for turning heads, yet he probably has never turned as many heads

as when he first started dating Evan Rachel Wood. Why, you ask

Because the musician was 17 years older than her. In 2006, Wood was 18

That's when she began her on-again, off-again relationship with Marilyn Manson. This was coming right on the heels of Manson's divorce from acclaimed burlesque dancer Dita

Vontese. Ultimately, they ended up dating for four years, and he even popped the big question

in 2010 on stage in Paris. However, they quickly split in 2011, and the actress moved on to marry

Jamie Bell. We're not sure what's more confusing. The fact that Seth MacFarlane has somehow remade

himself into a leading man, starring in films like A Million Ways to Die in the West and The

Orville, or the fact that he dated Amanda Bynes. Yup, we're as shocked as you, but it's true

The two briefly dated back in 2009. The pair were 12 years apart in age

Like VH1 said at the time, there is nothing more random than Seth McFarlane dating Amanda Bynes

You know 50 Cent as the rapper turned actor turned video game licensor turned energy drink tycoon

You know Chelsea Handler for being Chelsea Handler. well the two steamed things up after the rapper appeared on the late night host show back in 2010

no one would have pictured these two together but even after breaking up they remained good friends even flirting on social media here and there Just goes to show you opposites more often than not really do attract Billy Corgan legacy will always be his angst rock band the Smashing Pumpkins

Their music took the world by storm in the 90s. From songs like 1979 to anthems such as Tonight Tonight

Corgan established himself as one of the alt-rock Illuminati. And then he got old, became conservative, and kicked all the other band members out of Smashing Pumpkins

That was just the beginning, though. Here's where he really drove off a cliff

In 2009, Corgan began publicly dating social media personality and publicly professed Nazi

Tila Tequila. Despite everyone questioning the decision, he showed up arm-in-arm with the controversial

reality star to Bravo's A-List Award that year. Continuing to chronicle Corgan's love life, our next entry is about when the former rock

titan decided to spend some time with singer Jessica Simpson. Billy Corgan clearly has diverse tastes in women

They met when Jessica Simpson asked him to help her with the theme song for her docuseries, The Price of Beauty

That's when they started a brief romance. According to Billie, they were nothing. But Jessica, on the other hand, owned her feelings for the musician, even telling Allure, I definitely will marry an artistic man

Conan O'Brien is one of the most famous late-night talk show hosts in the history of the genre

He's also written for Conan O'Brien as one of the most famesons and the Harvard Lampoon

But did you know he dated a very famous sitcom star for years? That star Friends actress Lisa Kudrow Conan met Kudrow in an improv class The two dated for some time and then broke up Though we wouldn have pictured them together initially after thinking about it they do have a lot in common Too bad the relationship didn last Kudrow said in an interview

we found that we were both better as just friends. Jesse James and Sandra Bullock met when she

arranged a tour of his motorcycle garage. The two hit it off and began dating. If you're unfamiliar

James is most widely known for being the host of TV shows like Monster Garage and Jesse James

as a dead man. Bullock, obviously, is a world-renowned actress and performer, known for her roles

in Gravity, Miss Congeniality, Speed, and Bird Box. There is really no breakup story that will

get your blood boiling quite as much as the one that went down between these two. She was America's

sweetheart, and he was a bad boy motorcycle builder who cheated on her after being married

for five years. Safe to say the world will never forget that scumbag. Avril Lavigne is one of the

most successful Canadian singers of all time, coming in third behind Shania Twain and Celine Dion

She sold over 40 million albums and over 50 million singles. She's often credited with opening the door for more female pop-punk musicians to cement themselves in the mainstream

She also has criminally bad taste in men. Levine was married to both Sum 41's Derek Wibley and Nickelback's Chad Kroger

Do we really need to say more? However, sandwiched in between those two sparkling examples of bad music is Brody Jenner

Yeah, exactly. The former star of The Hills, Jenner and Levine dated for roughly two years before deciding

to call it quits. Apparently, they split up because Jenner wanted to focus on his career

Hope that's going well for you, buddy