Best And Worst: 15 Side-By-Sides Of Hollywood's Biggest Names

The 15 celebrities on this list have had tens of thousands of photos taken of them over the years. Their careers have had some incredible moments. Several of the women below have had their good looks celebrated by some of the biggest magazines in the entire world. But just because you know they're gorgeous, doesn't mean they don't have moments where they're caught looking terrible.

The reasons as to why they may look so disheveled will vary throughout the list. For Angelina Jolie, it was an addiction to drugs that got caught on camera. For Kate Upton, it was the pesky paparazzi who caught her on a bad skin day. Others like Kim Kardashian, Britney Spears, and Jodie Sweetin show the ramifications of having their photo taken while they were getting their drink on.

These celebrities may never have looked worse than in the moments we've captured below. But just to give them some credit, we've also tracked down some of their best and most memorable photos that help explain their superstardom. We hope you enjoy, these comparison photos of Hollywood's biggest name.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

15 Jennifer Lawrence

Some of the celebrities on our list were caught by the paparazzi at unsuspecting moments which results in some hilarious photos. With the above photo, however, Lawrence is clearly doing her best to try and make a hilarious face at the camera. The end result however while successful, does not paint her in even kind of the most flattering light!

We're sure Lawrence isn't too worried about people thinking she isn't sexy though. That being said, she is planning to dial up the sex appeal as a seductive Russian spy in her upcoming film Red Sparrow. The film is also starring Mary-Louise Parker (whom you may know from Weeds) as well as Joel Edgerton.

14 Jonah Hill

Now we need to preface immediately, the photo on the right of Jonah Hill was for a movie! He ballooned up in size for his role in War Dogs, but perhaps he's getting lessons from Christian Bale because he managed to lose that weight like it was seemingly nothing. At the very least, nobody can question that Hill is incredibly dedicated to acting.

The photo on the left is perhaps from Hill's most exciting (and upcoming) project titled Maniac that is coming to Netflix and also stars Emma Stone. The TV series is set to come out in 2018, y'know, provided that neither Hill nor Stone shoots their career in the foot by then!

13 Jessica Simpson

Jessica Simpson has had plenty of people criticize her over the years for her weight gain. Though when you consider she gained the weight because she was pregnant, it's definitely a low blow. But Simpson definitely isn't pregnant in the above photo on the right! Instead, she is definitely under the influence of copious amounts of alcohol that makes for a hilarious (albeit embarrassing) photo. Perhaps the photo, along with the logical hangover, will help her reign in her drinking the next time she is out for a night on the town.

The photo on the left also serves as a reminder as to why Simpson was largely considered to be one of the most attractive women in Hollywood during the height of her career.

12 Daniel Radcliffe

Daniel Radcliffe is always going to be recognized for his role as Harry Potter. But he's very fortunate his career survived the potential scandals that could have come with his addiction to drinking.

Radcliffe opened up about how extreme his drinking got and the potential impact it had, “I can honestly say I never drank at work on Harry Potter. I went into work still drunk, but I never drank at work. I can point to many scenes where I’m just gone. Dead behind the eyes.”

Radcliffe has since stopped drinking, but that doesn't make a photo like the one on the right disappear off the internet!

11 Angelina Jolie

Angelina Jolie is one of the most well-respected actresses in Hollywood, not only for her talents on the screen but because of all the amazing efforts she does to help improve the world. But there was a time in Jolie's life where her priorities weren't focused on helping those in need, but making sure she had access to a supply of drugs.

“I’ve done just about every drug possible. The worst effect, for me, was pot. I felt silly and giggly, and I hate feeling like that," said Jolie.

The above photo may be decades old now, but if Jolie saw it we're sure it'd be a painful reminder of when she was perhaps at her rock bottom.

10 Britney Spears

Britney Spears has had some solid moments in her career where she was considered to be one of the biggest sex symbols in the music industry. But as you can tell with our photo of Spears at her worst, she's also had some moments where she definitely let her drinking get away from her. But we suppose that's just the price you have to pay when you go partying with Paris Hilton!

The fact that it looks like someone is asking for an autograph is also proof that even if celebrities are sloshed out of their minds, that it just might mean they are going to draw even more attention towards themselves, and not for the right reasons. Nothing like battling a hangover the next day while also hoping drunk you didn't decide it was a great idea to flash the paparazzi!

9 Kate Upton

Kate Upton is one of the most recognized models in the industry. It definitely helps her case that she seems to be a mainstay in the Sports Illustrated Swimsuit Issue, which means there is always at least something to look forward to in summer! Upton has also recently made headlines after she officially tied the knot with her partner, Justin Verlander, who recently won the World Series with the Houston Astros.

We're sure the two have plenty of reasons to be celebrating, but Upton probably wasn't feeling too pleased when the paparazzi snapped this quick photo of her as she tried to go and tackle some errands. Everyone has tough skin day as Upton appears to be having, but not everyone gets those photos blasted everywhere.

8 Sofia Vergara

Sofia Vergara knows how to leave you in stitches with her hilarious antics on Modern Family. But she is also well recognized as being one of the most captivating women in Hollywood, both due to her winning personality and her incredible beauty.

With the above photo that we've tracked down on the right, however, you may not be left thinking how amazing she looks! Similar to Modern Family, it may make you laugh though.

It really is just a case of bad timing on Vergara's part as her makeup is clearly all done-up for the event. We're sure she's thankful that we've also included the photo on the left of her being prepared for the snap!

7 Kim Kardashian

There might not be a bigger name in Hollywood than "Kardashian". It doesn't matter if we're talking about Khloe, Kourtney, Kim or the Jenner clan of Kylie and Kendall - it's clear these 5 women take up a lot of the tabloid journalists time.

But while Kim has thousands, literally, of photos that we're sure she is more than happy to blast all over social media, she must absolutely hate this photo of her getting her drink on at the club. She's just fortunate photos don't exist of her trying to walk after she got to the end of the bottle!

As for when Kim looked her best, maybe you're partial to when she made you nostalgic for your childhood with her rendition of Jasmine.

6 Katy Perry

Katy Perry and Russell Brand surely had plenty of fights that led up to their divorce. You imagine at least one of them had to be centered around the fact that Brand uploaded a photo of Perry only moments after she was awoken, and as you can tell, also not wearing makeup.

Perry is no stranger to going makeup free, including appearing as such at times in her documentary about her music career, but this above photo (which was quickly deleted) is one moment she wishes she could have back. One thing that may help you forget it though is getting to stare at how stunning she looks in the photo we've selected of her on your left!

5 Nicolas Cage

It must be exhausting sometimes to be a celebrity and to constantly be hounded by fans for photos. I mean sure, it's tremendous that they respect and appreciate your work, but you're still only human! One of the biggest downfalls can also come with the fact that if a fan catches you on a day where you aren't feeling particularly attractive, are you really going to say "Nah sorry, feeling too ugly for a photo today"?

But considering the well-known nature of this Cage fan photo, which was originally posted to Reddit by user EffThisImOut, we're sure he wishes he had just said no!

Cage's career has had ups and downs, but if you're looking for a well-reviewed Cage flick make sure you see him in Leaving Las Vegas that won him various awards.

4 Selena Gomez

Selena Gomez is recently making headlines due to her separation from The Weeknd. Not helping take her name out of the headlines is the fact that she is also spending an increasing amount of time with her ex-boyfriend Justin Bieber. And while Bieber has plenty of unflattering moments in his life, we're sure you don't mind getting to stare at a stunning photo of Gomez on the left and a hilarious one on the right.

With the amount of paparazzi attention that Gomez has gotten throughout her life, we're sure this is going to be far from the last time she gets caught with her face at an unflattering angle. Let's hope she was able to laugh it off when she saw the photo the next day, especially when we're sure there were plenty of photos from that night where she looked amazing.

3 Jodie Sweetin

When talking about her past drug use, Jodie Sweetin said, "I wanted to prove that I could get more trashed than anyone. There were times I did so much coke, I’d be there laying there, getting sick and thinking ‘I’m going to die.’ But I didn’t care.”

That's definitely not the best mentality to be having when going out for a night on the town! Sweetin's ability to kick her addictions should be commended. Her good looks were perhaps never put on more display than when she was on Dancing With The Stars where she ended up finishing in 6th place. We're sure Sweetin's story has helped inspire many fellow celebrities who have battled addictions, as well as many fans who grew up loving her.

2 Emma Watson

There aren't many photos out there that exist that paint Emma Watson in a bad light. She really is one of the most beautiful women in Hollywood, but one of the downfalls of being so popular is that there are thousands of photos being taken of you at every event.

Which means that along with Watson suffering some wardrobe malfunctions in the past, she has also been on the unfortunate end of her face being caught looking like the photo on the right. We don't even know how she managed to get her face in that kind of pose, but something tells us if we asked her, she wouldn't know either. Perhaps somebody had tried to cast a spell of ugliness on her!

1 Charlie Sheen

Charlie Sheen was once one of the most recognized actors in Hollywood due to his role on Two and a Half Men. Not to mention several classic films such as Platoon and Wall Street. But you never want to have a moment in your life, much less if you're a celebrity, where you are literally shoving cigarettes in seemingly every available orifice. Because having a sense of smell is totally overrated right Sheen?

If it's any consolation for Sheen, there's probably a pretty good chance that he has a hazy memory of doing this. Sheen attempted to find success with another sitcom, Anger Management, after leaving Two and a Half Men but it was canceled after 100 episodes.

More in Entertainment