20 Uncomfortable Photos Of Celebrities With Michael Jackson

We've all heard the questionable rumours, we've listened to stories of controversy, and we've heard countless people badmouth Michael Jackson long after his time abruptly came to an end on June 25th, 2009. However, let's sweep that under the rug for a moment. No matter how you feel about MJ, and regardless of whether or not you believe the allegations that have been thrust onto the table, not a single person on this planet - music industry figure or not - can deny the fact that MJ was the artist of a generation - they didn't call him the King of Pop for nothing.

As a high-status celebrity, perhaps higher than all others, Jackson had ongoing interactions with countless famous faces. While many of these consisted of heartfelt, friendly moments, there were a handful of snapshots that depict awkwardness, embarrassment, peculiarities, or just give us a touch of the creeps.

20 Little Baby Ariana Grande

via YouTube

Don't worry, we also had to do a double-take on this one. Yep, that's actually a mini-me version of the pop sensation, Ariana Grande. While she's still a rather small human in adult form, it all seems a little perplexing to see her as a young girl hanging out alongside the King of Pop.

19 Halle Berry's Blank Eyes

via Twitter

Oh hey there, Halle Berry, why such the long face? While her smile might say I'm happy to be here, Halle's dead eyes tell an entirely different story - get me out of here! This throwback pic of Michael Jackson and Halle Berry is originally from the Bambi Awards ceremony back in 2002.

18 The Little-Known Akon Friendship

via Twianon

On the left, we've got our moonwalkin' MJ and on the right, we've got the 46-year-old American rapper-producer and father of six, Akon. While it might come across as a bit of a surprise, these two were actually friends back in the day. Akon posted this pic back on the 29th of August, 2018, with the caption "Happy Birthday MJ miss you! #KingOfPop."

17 Mad For Madonna

via AP Photo/Kevork Djansezian

Speaking of The King of Pop hitting up the dating world, does anyone recall when he strolled down the red carpet at the 1991 Academy Awards? Alongside him was an infamous music sensation in her own right - Madonna. We can't tell if this fling is cute or just a little too weird.

16 The 'Obsession' With Britney Spears

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It's not exactly a wild secret that MJ and Oops I Did It Again star Britney Spears performed together over the years. What is, however, a little lesser-known is the fact that the pair faced allegations that that MJ "had an obsession" with Britney. If this image says anything about it, perhaps there was some truth behind the claims.

15 The King Of Pop And The Princess Of, Well, Wales

via Biography.com

While The People’s Princess and the King of Pop both earned their own royal-themed moniker, their connection went far deeper than that. It brewed from the fact that Diana was actually a huge fan of MJ's music. It this photo, however, we're a little concerned with the fact that Michael is so elated to be holding his own memorabilia.

14 Beyonce's Cheek Snuggle

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Few musicians of the last 50 have boasted as shimmering a spotlight as Michael Jackson. One name that could arguably be thrown into the same hat is none other than Queen B, Beyonce. Here they are, pictured on stage together, in what can only be described as an awkward cheek nuzzle.

13 So Much Talent In One Awkward Photo (MJ & Freddie Mercury)

via Wikimedia Commons

Wow, there you have it. We never thought that Michael Jackson and Freddie Mercury would end up side by side in a photo, but the proof is in the pudding. This snap dates back to 1983, when Freddie recorded a few tracks with MJ that have remained locked deep away in Queen‘s vault. What a sound that must be...

12 'I'll Smile, You Just Look At Me' (With Stephanie Mills)

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Alright, next up on our list of somewhat awkward yet certainly double-take-worthy pics of MJ and different celebrities, we're welcoming American singer, songwriter and actress, Stephanie Mills. At first glance, she appears to be overflowing with glee in this photo - Michael, on the other hand, a little less so.

11 Diana Ross Was A Cougar

via insideedition.com

While Diana Ross might be donning a huge ear-to-ear grin, MJ apparently didn't get the 'say cheese' memo, blankly staring off into the distance in a true awkward fashion. Believe it or not, the pair actually dated for a little while, although the fact that Diana was close to 25 years older made things interesting.

10 The Cliche Pose With Tatiana Thumbtzen

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In case you haven't seen the music video for The Way You Make Me Feel, then firstly, have you been living under a rock? And secondly, it stars this lovely lady - Tatiana Thumbtzen. She actually came out and declared that her relationship with The King of Pop went far beyond just that music video.

9 This Is Just Too Much Hair (With Cher)

via thesun.co.uk

We're going all the way back to the early days of the Jackson 5 for this one! When MJ was just part of a group act, Cher worked closely with him. Despite showing plenty of admiration for his talent, she didn't hold back in a TV Guide interview in 2003 when she declared that "the guy was nuts". Well, we think that hair is nuts.

8 That's Not How You Ballroom, Tatum O'Neal

via thesun.co.uk

Michael Jackson's first publicly documented relationship was with Oscar winner Tatum O'Neal. They became friends when she was 12 and he was 17 and soon after, a relationship blossomed. In a 1982 edition of Jet Magazine, he said that their love had "cooled off" and they ultimately decided to be just friends.

If you're scratching your head trying to figure out who Tatum O'Neal is, she boasts the title of the youngest person to ever win an Academy Award (in 1974), at the tender age of just 10. That's not her only 'first' feat - she was also MJ's first publicly-documented relationship, when he was 17 and she was 12. That age difference just doesn't feel right.

7 Steven Tyler, What Are You Doing?

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For those unaware, Steven Tyler was the frontman of the infamous rock band, Aerosmith. Here's the singer was spotted alongside Michael at the opening of Studio 54 in New York City, back in 1977. Stephen Tyler's bizarre hairstyle is one thing to note, as is Michael's slightly creepy appearance.

6 Prince's Peculiar Prop

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Okay, let's talk about the obvious first up - what the heck is Prince holding in his left? It's either an obscure microphone, a potato shooter, some poorly-designed brass knuckles, or an actual golden-plated weapon. Maybe it has something to do with the bitter rivalry these to music superstars had.

5 ET And MJ

via Pinterest

Okay, we hear you, folks. We know that E.T isn't technically a human celebrity, however, he's arguably more famous than the rest of the names on the list put together. Whether you love or hate the movie, and regardless of how you feel about MJ and his controversy, you can't deny that this photo is kind of cute, albeit in a weird way.

4 That Side-Eye Though

via Consequence of Sound

There's just so much going on in this photo that it's hard for our eyes to pick a place to focus on and stay there. How about MJ's piercing stare and smirk? Or perhaps it's that seriously creepy get-up on the man in the background. What about Macaulay Culkin's hat - where'd he get that from?

3 A Little Lovin' For Whitney Houston

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That's right, ladies and gentlemen - a young, glowing Whitney Houston alongside Michael Jackson at his Neverland Ranch! We heard from his former bodyguard, Matt Fiddes, that the pair actually had a quick fling for a couple of weeks (as told during his interview on the Today show in 2012). Who would have thought it?

2 Proof Eddie Murphy Should Stick To Films

via IMDb

We'll ignore the fact that Eddie Murphy is looking a hell of a lot like Freddie Mercury in the photo and lean of focus more toward the pure awkwardness of the whole situation. Granted, this snap is from the 1993 track Whatzupwitu (Eddie Murphy Feat. Michael Jackson), however, that doesn't excuse the embarrassing green screen background.

1 Oh Hey There, Lisa Marie Presley, Wanna Get Married?

via biography.com

We have to wind the clock back all the way to when the King of Pop was merely a teenage prince - at the tender age of 16. This is when he first came face to face with the daughter of music god Elvis Presley. It might be hard to believe that the pair ended up dates - in fact, they got married as well!

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