15 Pics Of Freshly Dumped Celebs Looking Like Shleps

No one likes going through a break up, period. You invested years (or days) in a relationship with another person, only to have it blow up into little shards in the long run. And it's especially rougher than usual if you're the person being dumped. When mere mortals go through a falling out with their significant other, we're able to mourn in private. We can perch ourselves in front of a Netflix show and just bawl our eyes out into a pint of Ben and Jerry's like normal people. But newly dumped celebrities have it way worse considering the fact that there are paparazzi lurking around every bush. They can't just walk outside after crying their eyes out because if they do, they'll just end up on the cover of Star followed by some heinous caption about how bad they look. Consider us normal individuals lucky. Here are 15 celebrities that were caught looking less-than stellar after a break up.

15 Macaulay Culkin

Actor Macaulay Culkin has had his share of heartache. First, he was shoved into acting by his overbearing father who just ended up trying to swindle all of his hard earned money. Then there was that whole Michael Jackson debacle, eesh. Needless to say, the man has had it rough. As you may or may not remember, Culkin once dated Mrs. Ashton Kutcher herself - that's right, he was once paired up in a long term relationship with Mila Kunis. When That 70's Show was still going strong, Kunis and Culkin began dating and notoriously keep their relationship private for eight freaking years. Mila was just 16 at the time they started a relationship and wasn't used to dating someone as famous as Culkin. After the duo finally parted ways, Macaulay looked like the grease-fairy set up camp full time in his hair.

14 Britney Spears

Poor, Britney Spears. Everything was all fine and dandy back in the day when she was dating the only N'Sync-er with any promise. Remember those matching denim outfits they wore to the MTV movie awards? Ah, good times. The pop singer's entire life has been one death-defying roller coaster after another - the girl couldn't catch a break from the press until recently. That could be because she had some very public and disastrous relationships attached to her name. I mean, she married a dude in Las Vegas for about all of three seconds and then had a harsh melt-down. As you can see, Spears went through some pretty heavy crap after some break ups. But who can really blame her? You'd lose your senses too if you were married to Kevin Federline. She's back to being on top of her game now, however. Whew!

13 Amanda Bynes

This actress has had her share of problems and she's dangerously walking that “Britney Spears Crazy” line. Actually, come to think of it, she flew past that line at warp speed. While she was once a Disney-darling, Amanda Bynes these days can't seem to track down her own sanity. And this probably has to do with constantly being on the receiving end of dirt-poor relationships (and yes, I'm including being dumped by her drug dealer and her management team too). It seems like every time she's dumped by one thing or one person, she takes to the streets and ups the crazy a notch or 12. Sure, we've seen her in weird butt wigs and such, but it's when she's looking like she's packed on some weight and looks just plain… well… depressed… that's when we start to genuinely worry.

12 Demi Moore

Actress Demi Moore can't seem to really catch a break with the press OR with life in general. Years ago, her marriage to Ashton Kutcher fell apart just before she turned 49 years old (the That 70's Show star was only 33 at the time) thanks in part to rumors about his infidelity. She "said" to have taken the divorce “okay” in a sense, but her stepping out and walking the runway looking like a damp corgi speaks otherwise. She looked like she went through a chaotic downward spiral after they parted, and it couldn't have been a cake walk to hear that Ashton is now living happily in bliss with his new little family thanks to Mila Kunis. Moore even allegedly suffered from seizures after the duo separated and had to be hospitalized. While it's been years since the split, Moore appears to still be living in the shadow of her past relationship and heartache.

11 Katy Perry

Katy Perry has been through her share of hard break ups. First, she married a man who was WAY beneath her (seriously? How strong were those beer-goggles she had on for so many years. I mean, Russell Brand? SERIOUSLY?) only to be broken up with in the form of a text message. Yes, you read that right. Brand seriously text messaged her asking for a divorce. That's a massive hit to the self-esteem right there. So naturally, as if it is a celebrity right of passage, Perry had to take the walk of shame after the separation went public, poor thing. But, since Katy is Katy Perry, she bounced back hardcore and started dating others (like dumb dumb John Mayer) and we all thought she found new happiness with Orlando Bloom (can you say “naked paddle boarding”??), but that relationship fizzled out after only a short year. Though they're still close friends, so that's always good.

10 Kylie Jenner

Okay, yes, this is Kylie Jenner looking like a shlep - with low key make up on her very plastic face. This is her posing with then-somewhat-bro-in-law Scott Disick, looking all laid back and casual in her clothing style, makeup, and demeanor shortly after her split with Tyga after reports were surfacing about his many infidelities. From the looks of it, the press believed that Jenner actually rebounded WITH Disick after these photos were snapped. I mean, Disick looks more like a shlep than Kylie does. Do you really expect a Kardashian to be caught dead looking like a hot mess after a break up? I think not. You've seen her sisters go through it multiple times in the past to know better. Unless your name is Rob, you won't catch a Kardashian off her game. Slightly, maybe, but not completely off.

9 Justin Bieber

Here's yet another celebrity that goes through relationships like it's absolutely nothing. First, he and Selena Gomez parted ways and he decided to write a whole sappy album based off of it, and now he's reeling in the wake of his dead relationship with Sofia Richie. I mean, should you even call it a “relationship” if you only dated for around a month? Well, that's what all the magazines are calling it. TMZ reported that Justin Bieber broke it off with Richie and that they're already “seeing other people”. This particular picture was taken BEFORE his relationship with Sofia while he was still mourning his failed relationship with Selena and nailing other women in order to get over her. The shaved head look isn't the most desirable and just makes him look like a lost hobo.

8 Amy Winehouse

Nothing, and I mean NOTHING, was more tragic than 27-year old Amy Winehouse's death back in 2011. Expect perhaps the way she was living at the time. Winehouse was at the height of her career winning Grammy after Grammy, composing groundbreaking albums, and selling out her concerts. However, booze, drugs, and abusive relationships kept muddying up the water. Sure, it made for amazing music, but it was literally killing her slowly. This particular photo was taken after a row with her then on-again-off-again boyfriend (not to mention a row with crack as well, I'm sure). Winehouse never really cared about what other people thought of her in these situations and was perfectly okay with telling the press to screw off whenever she went out in public looking like she was just dragged by a Mack Truck for a few blocks.

7 Rob Kardashian

Oh god, THIS guy. You have to hand it to Rob Kardashian, he makes looking like a lowly drunk overweight dude seem fabulous. As we all have heard by now, Rob went on an Instagram and Twitter rampage against his former boo Blanc Chyna and posted some NSFW videos of her on his social media pages. According to California law, Rob could face some criminal charges by posting what's known as “revenge p*rn” against his baby momma, so the outlook doesn't appear to too sunny for this particular Kardashian. You have to give credit to the dude though considering he's the bravest of all his relatives. I mean, you need to have a certain amount of bravery to assume that the “bowling alley white trash dad” look is in. I can almost smell the beer breath just by looking at this photo.

6 Kris Humphries

Given, this guy looked like a giant dork even before he married into reality TV royalty. Years ago, Kim Kardashian made one of the biggest mistakes of her life by rushing into yet ANOTHER marriage with someone lower on the social ladder than she. Maybe she just took pity on him? Maybe she assumed that all the Kardashians had to marry NBA stars? Either way, her marriage to Kris Humphries expired before the milk in her fridge did. During that time, Humphries was being tossed around by NBA teams (because, well, he wasn't a good player after the Kardashian family got their slimy paws on him - something known as the Kardashian curse in the NBA world) and went out looking like a crushed up bag of grey Doritos. OMG WAS HE GOING TO THE BOSTON CELTICS, WAIT, WHO THE HELL CARES?

5 Miley Cyrus

Miley Cyrus seems to go through this crap every other week. Especially when it comes to fiancee Liam Hemsworth. They apparently have broken up 3450383048 times since becoming a thing after filming their movie The Last Song together. And with every break up, Miley just continues to look worse and worse every time she sets foot outside. But yet, Liam always looks smoking hot - what gives? Apparently, these two happen to be the tabloid's latest punching bag and they're now reporting that the duo has called off their engagement YET AGAIN. I wouldn't be too shocked if this is true since they're constantly going back and forth with each other. Just make up your mind before Miley shaves off all her hair and cuts her ears off (seems like something she would do just because).

4 Robert Pattinson

What's worse? Being in the Twilight franchise or being dumped by someone who starred with you in the Twilight franchise? I want to go for the first one, but that's just me. Everyone remembers when actor Robert Pattinson dated the moody Kristin Stewart before she cheated on him with a married director. Fans of Twilight and Pattinson were quick to crucify Stewart after the photos were released of her affair, but they still have yet to crucify Pattinson for his crappy acting abilities. And, like celebrity clockwork, the paparazzi was on Robert's tail, hoping to snap a soul crushing photo of the actor crying over the loss of a soon-to-be lesbian (and, by the way, I adore her so much more now that she's out of the closet). And look! They got one!

3 Selena Gomez

Much like her Kardashian counterparts, it's pretty hard to find a horrible picture of Selena Gomez looking, well, horrible. But it appears as if we happened to stumble upon one! This average looking photo of Selena was shot shortly after her parting with then-boyfriend Justin Bieber, who she was serious about for a while. I mean, why would you look so sad after breaking up with JUSTIN BIEBER? I don't understand why she's not running through the streets, screaming for joy. I mean, she finally got out of that trap for good! Rejoice, woman! But, alas, I guess she loved him or something because she looks pretty damn sad here. He also happened to go through his own mourning period as well, only he was bed-hopping with models rather than slinking about (though he looked pretty sad in those pictures of him with the models, so there's that).

2 Charlie Sheen

I think I'm more shocked these days when I see a picture of a normal looking Charlie Sheen rather than one where he looks like he was deep friend in crazy. Sheen just recently announced that he is HIV positive, which took a lot of balls to tell the public. But he had been in a downward spiral since the 1980's. So, pretty much his entire life up until this point. Though, Sheen tends to look even worse AFTER he goes through some very public break ups or shattered marriages. Remember when he looked like an entire high rise building b*tch slapped him in the face after his separation from Denise Richards? Or in this picture where he looks like he just crawled out of a college frat house after his divorce from Brooke Mueller? Get it together man, you already have one foot, arm, and part of your torso in the grave.

1 Drake

There is nothing worse than looking like a kicked puppy after the supposed love of your life starts dating a billionaire after breaking it off a final time with you. This happens to be the case when it comes to poor Drake and his tragic, Shakespearean-like unrequited love for fellow singer Rihanna. They had been dating on and off since 2009 and while he saw himself as a white knight sent in to save the damsel in distress, Rihanna appeared to think of Drake of more as a rebound. He wrote a great deal of songs about the beauty and his love for her, while she just struggled and shoved him in the friend zone for life. So no one can really blame him if he looks so desperately sad after another break up.