Hollywood star Lindsay Lohan first had her taste of fame when she starred in Disney's 1998 family comedy The Parent Trap, which undoubtedly became a classic by now. Later on, movies such as the 2003 Freaky Friday and the 2004 Mean Girls turned Lindsay into one of the most famous teen stars on the planet, and everyone was sure LiLo would become a Hollywood staple. Unfortunately, with fame came plenty of Hollywood parties, and Lindsay may have taken that part way too seriously. Today we're going to look at some photos the actress surely wishes were never taken, but unfortunately for her — the internet never forgets. From her nights out, over some awkward court moments, to rather strange fashion choices, Lindsay is truly the queen of cringe-worthy photo moments.
Here they are — 20 photos of LiLo that will make you laugh, cry, but most of all feel pretty bad for her.
20 Let's Start Off With The All Times Her Eyes Just Wouldn't Cooperate
Lindsay Lohan clearly seems to have a new signature look, and well, we're not too sure it's a good one... Jokes aside, it was probably just a strange eye moment that got captured in these two pics of Lindsay, but we had to include them as they are too funny not to!
19 Obviously, We Had To Include Her Mugshots — There Are Plenty To Choose From
Lindsay is pretty much the ultimate queen of mugshots in Hollywood — she has a total of six so far. Most of them are due to driving under the influence, and we have to say, the actress does not look as bad on them as we'd anticipated. Some could even pass as a cute insta pic.
18 Then There Are All The Times She Was Photographed With A Drink
It's no secret that Lindsay likes to have a drink or two. But by now we all know that most of those drinks have lead the actress to some very bad decisions and she probably wishes she could erase all these pics. On the bright side, it seems as if she's doing better — or at least not drinking in public anymore, as photos like these are very rare nowadays.
17 Which Often Led To Her Tripping And Falling
There's just something about seeing another person trip and fall that will always make people laugh. And well, when it's a celebrity it almost seems even funnier. We know, we know, we really shouldn't laugh at another person's suffering, but just look at these pics of LiLo tripping and falling!
16 And Also Passing Out In A Car
Most of us have been there — you have a couple of drinks too much and next thing you know is that you know nothing at all and you are sleeping in the most uncomfortable position. And that is pretty much what would happen to Lindsay after every night out back in the days, and here's a pic to prove it.
15 Like Mother Like Daughter, Huh?
Now we have always wondered how come Lindsay is such a hardcore party girl, but then we've seen pics of her mom on nights out and everything was crystal clear — it's in Lindsay's blood. And while we can't help but judge them when they party together, we're also kind of envious, like who parties this hard with their mom?
14 Lindsay And Self-Tanner Are Clearly Not A Good Combo
Anyone who ever used self-tanner by themselves has been there — it's really hard to get it done right and streaks are so common. Having that said, when you're a celeb we kind of assume you can pay someone to do it for you so that photos like these never get taken.
13 As They Often Result In Hands Like These
Okay, to be fair enough, we're not really sure why LiLo's hands look the way they do here, but it does seem as if she may have forgotten to use the self-tanning applicator mitten, which is why her hands look like that. Let's hope Lindsay learned to always make sure her hands are clean before a red carpet event.
12 Hair Extensions Are Also Not Lilo's Best Friend
Okay, everyone has a bad hair day every now and then, but when you're a celeb you have to count that a bad hair day can easily end up all over the internet. Which is exactly what happened when LiLo left her home and forgot to check the back of her head. Oopsie!
11 Lindsay Is No Stranger To Crying In Public — Life Is Too Hard Without A Drink In Hand
We have absolutely no clue what is going on in these pics, but one thing is sure — Lindsay is pretty upset. Seems as whatever the two above were talking about completely riled up LiLo to the point that she couldn't stop herself from crying on the way to the car.
10 During Her Court Appearances Lindsay Tried To Wow The Judge With Her Charcoal Bronzer
This is certainly one of the most hilarious attempts at bronzer we've ever seen, and we have no clue how nobody told Lindsay her bronzer is way too dark and gray. If she thought this look was somehow going to make the judge like her more, she was absolutely wrong!
9 Which Obviously Didn't Work
We are not sure what Lindsay was expecting, but judging from her reaction it seems as if she thought being a celebrity meant she would certainly be forgiven, and any charges would just go away. Luckily, that's not how things work, which seemed to have caught the actress by surprise.
8 But Hey, Life Must Go On, And A Monitoring Device Might As Well Be An Accessory
Of course, once she recovered from the shock, life had to go on. So here she is, making bikini appearances with a rather unusual accessory. Oh well, we can judge and laugh all we want, but ultimately the joke is on us because Lindsay is still making money and no monitoring device will ever stop her from that!
7 Lindsay Behind The Wheel Is Never A Good Idea — Someone Take This Girl's Drivers License
We already mentioned that LiLo has been caught several times while driving under the influence, which is why images like these always slightly stress us out. Lately, the party queen hasn't been caught behind the wheel too often, so hopefully we won't get to see too many of these pics in the future.
6 Her Fashion Choices Are Also Often Questionable
Back in the days when Lindsay was a teen icon, her fashion style was copied by girls all over the world. Fast forward to today, and you'll catch most of us cringing at some of her outfit choices. There's nothing wrong with experimenting with fashion, but Lindsay, please try to stay away from mesh pants.
5 Yeah, We Don't Know What's Going On Here Either
Honestly, who knows — all we do know is that a seemingly drunk Lindsay was photographed by someone with a pretty good camera aka something like an impromptu photo shoot happened. And yeah, let's not comment on Lindsay's go-to poses — well just blame those on having a couple of drinks too much.
4 Look At Lilo Showing The Paparazzi What's Good
This pic from Lindsay's younger days always cracks us up because we can just hear Lindsay threaten the paparazzi that she's going to take a photo of them — and then actually doing it. Who knows, maybe she just wanted to remember the moment forever and has the photo stashed away in some type of burn book.
3 Oh, And There's That One Period She Wore A Hijab To Make Headlines
Back in 2017, there were plenty of rumors about Lindsay converting to Islam, especially after the actress was seen wearing a hijab on several occasions. Well now it's 2019, and Lindsay still hasn't converted which makes us think all of this was probably just a publicity stunt — and it worked!
2 This Is What Lindsay's Bad Pics Used To Look Like Back In The Days — An Innocent Marilyn Monroe Red Carpet Moment
Teen star Lindsay was the epitome of innocence, and her worst moments could be summed up in this photo of her on having a little fashion faux pas on the red carpet. Back then we had absolutely no idea how bad things would eventually get and that seeing pics of Lindsay on the pavement in front of a club would be just your average Tuesday.
1 And Nowadays We're Not Even Shocked To See Her Fall Out Of A Club
Yup, this actually happened. At least it seems like LiLo had a fun night, so having the whole world judge her may have been worth it. Either way, there you have it — if anything we can't deny that the former teen star turned ultimate party girl has a pretty eventful life!