The world of celebrities has given us some pretty strange pairings over the last few decades but the top of that list is none other than Chelsea Peretti and Jordan Peele.
Have a look for yourselves…
But first, let’s check out some of the other current and former couples that had us scratching our heads starting off with Macaulay Culkin and Brenda Song.
Every couple of years, I forget this pairing exists until they make headline news and then I’m confused all over again.
The most recent was when they announced that they became parents for the first time.
Song gave birth to their daughter, Dakota, on April 5th and they were said to be “overjoyed” at the prospect of parenthood.
The unlikely duo met on the set of Changeland alongside their co-star Seth Green who told Esquire that he “didn’t see that coming” when talking about their relationship.
Neither did we, Seth, neither did we.
(BTW this isn’t Macauley’s last appearance on this list!)
Tom Cruise and Cher.
Who would have thought, eh?
Tom and Cher dated back in the ’80s and are still good friends to this day.
In an interview, she even went on to name him as one of her top 5 lovers. Damn!
Jennifer Lawrence and Chris Martin.
I bet you forgot this relationship even happened… So did I.
Coldplay’s frontman dated the Silver Linings Playbook actress after he split from Gweneth Paltrow.
But the relationship didn’t last long. I guess it’s safe to say the two were just not right for each other.
Chelsea Handler and 50 Cent.
Now, two different words really collided with this unique pairing.
On the surface, it may seem like these two have little to nothing in common…
But it turns out they had enough to stay together for a few months.
Even after their breakup, they still speak very highly of each other so we can only assume they ended the fling on a good note.
Prince Harry and Meghan Markle.
Probably one of the world’s most controversial couples ever. No one saw the British prince falling for an American actress.
Initially, the pair met in July 2016 after a friend set them up on a blind date but the pair took their relationship to new levels when they officially tied the knot in May 2018.
Now they’re expecting their second child together very soon!
Soon-Yi Previn and Woody Allen.
From one controversial couple to another, but for an entirely different reason, Soon-Yi Previn and the disgraced director, Woody Allen made headlines all over the world.
Soon-Yi Previn was Allen’s adopted daughter before the pair decided to swap out the father-daughter relationship for a husband-wife one.
Woody repeatedly declined any wrongdoing, as he never saw himself as a “father figure” to Previn but… I feel incredibly uncomfortable even thinking about the fact that they went on to have 2 children together.
Ew. Just ew.
Brody Jenner and Avril Lavigne.
Jenner was not technically a skater boy but clearly, that didn’t matter too much to Lavigne as the pair dated for 2 years until she decided to say “see you l8r boi.”
Throughout their time together, they looked pretty loved up and even got matching tattoos together.
We’re kind of sad this one didn’t work out.
Kourtney Kardashian and Travis Barker.
And staying with the Kardashian/Jenner family, up next we have Kourtney Kardashian and Travis Barker.
If you say you saw this coming, I know you’re lying.
The pair might have only started dating 5 months ago, but they move pretty fast. Already, Kourtney’s plastered a few new tattoos on her Blink 182 boyfriend with many more to come, if he’s got any room left on his body.
Angelina Jolie and Billy Bob Thornton.
Before Brad, we had Billy.
While embarking on her rebellious phase, Jolie dated actor Billy Bob Thornton. The 2 were so committed to each other, they wore vials of each other’s blood around their necks.
Thank God that’s over.
Nick Jonas and Priyanka Chopra.
Again, did not see this coming but was pleasantly surprised.
As Nick Jonas took more steps into the world of acting, he stumbled across Bollywood-turned-Hollywood superstar Priyanka Chopra and the 2 immediately hit it off.
Fast forward a few years and a few weddings and the pair are living very happily together.
Megan Fox and Machine Gun Kelly.
When the rumors surrounding this iconic couple first came to light, we assumed it was just fans getting a little too excited as the pair were publicly working together on Machine Gun Kelly’s “Bloody Valentine” music video.
But then we saw them together outside of work and suddenly, it was all possible.
The pair later confirmed their relationship and have been serving us too much PDA ever since.
Halsey and Alev Aydin.
After dating the likes of G-Eazy and Yungblood, both known for their wild antics, we didn’t see Halsey settling with the more sensible option that is Turkish screenwriter, Alev Aydin.
Even though they have a 10+ year age gap, the two have found happiness with each other.
Halsey is even expecting a child with Aydin very soon!
Kid Rock and Pamela Anderson.
Back to another classic.
At the time, this couple seemed obsessed with each other, but clearly, it was a different story behind the scenes.
After they split Kid said: “I knew it was a bad career move to get involved with her because your life becomes a circus — because that’s what she wants is media attention.”
Taylor Swift and Tom Hiddleston.
Taylor Swift really loves British men and Tom Hiddleston was probably one of her best, but most unlikely, picks.
However, because the couple got together less than 2 weeks after her split with her then-boyfriend, DJ Calvin Harris, things went from awkward to bad.
This was because it was reported that Swift met the Marvel actor before that and it could have been what led to the Harris break up. But of course, it’s all just speculation as neither confirmed it.
But Harris did tweet: “Oh boy it’s about to go down,” with skull emojis and then deleted it later on.
Macaulay Culkin and Mila Kunis.
Do you remember this? Because I sure as hell don’t!
It was reported that these two actors dated for around 8 years… 8 whole a** years and I didn’t hear about it once?
Obviously we know it didn’t work out because Macaulay’s now with Brenda Song and Mila with Ashton Kutcher.
Justin Timberlake and Rihanna.
Again, very strange, but actually very iconic.
Even though the fling was brief, I bet they’re both glad it happened.
Plus we got the song “Rehab” out of it so we all win.
Cameron Diaz and Benji Madden.
The unlikeliest of couples, but probably one of the strongest.
Even though this couple prefers to keep their relationship under wraps, we have seen some adorable moments between them, including Madden’s touching tribute to his wife on her birthday.
“So many things that make me so proud of you and how special you are. Thank you for being the best friend and partner to me and taking this journey of Marriage.”
He continued: “The way you live your life everyday, and your compassion for the world shines thru in your eyes and you inspire me to want to be the best man I can be in this lifetime. You’re the realest. I’m so grateful to be yours Always&Forever, and to call you my One&Only. True Love.”
Cute… But still strange nonetheless.
Mary-Kate Olsen and Olivier Sarkozy.
This pairing really caught us off guard back in 2014.
It was mainly because of the massive age gap between the two, a total of seventeen years!
Mary-Kate started dating Olivier in 2012 and the 2 were engaged by 2014 but just 5 years later, the two have now finalized their divorce so I guess it wasn’t meant to be after all.
Sarah Paulson and Holland Taylor.
Another couple with one of the biggest age gaps in Hollywood, a whopping thirty-two years.
Unlike Mary-Kate and Olivier, age seems to be but a number for the lovebirds.
This is actually one couple we can stan.
And now finally, Chelsea Peretti and Jordan Peele.
Separately, these two are pretty iconic, but together it seems as though they’re even better!
It’s just yet another pairing we didn’t see coming but we’re loving.
The couple first met in 2013 and sloped just 3 years later. They even have a child together, Beaumont who is 3-years-old.
So there we have it, some of Hollywood’s strangest couples.