Lindsay Lohan has sure come a long way from the freckle-faced redheaded twins in 1998’s The Parent Trap to, er, whatever it is she’s doing these days. And can you believe it’s been 13 years since Mean Girls was released? That means an entire generation of future mean girls has been born, raised, and unleashed on junior high since we first met Cady and The Plastics. Just in case you needed to feel old.
Speaking of old, it’s hard to believe LiLo is actually 30 years old now, mostly because she’s looked like a 45-year-old for at least a good quarter of her life in the spotlight. It is unclear when exactly things started unraveling, but boy has it been fun to watch. You know how people compare it to a car crash? Nah, a car crash is way too dramatic. This is like those time lapse videos on YouTube showing a tomato rotting over time. A tomato takes a few months to go from deliciously red to a pool of rotten sludge, somehow Lindsay Lohan managed to drag the process out of a period of years. Say what you will about her, she was certainly dedicated.
Nowadays, she’s speaking in a funny accent, helping Syrian refugees, and carrying around a Quran because why not. Would it be wrong of us to say we kind of miss drunken, panty-flashing, fire crotch LiLo? She was a blast.
She was also pretty scary sometimes. Thank goodness the paparazzi were there to capture every embarrassing moment of her live-action trash telethon.
16. Good Thing She Had A Designated Driver Trash
It’s 2am, do you know where your Lindsay Lohan is? Surely she didn’t.
Before you rush to laugh at this photo, just know that this is exactly what you yourself look like in your Uber home from the club waiting in the Taco Bell drive-thru trying not to throw up.
The scariest thing is that she looks like she could go from telling you just how much she loves you duuuude 15 times over and smack you over the head with her purse the next. Maybe it’s that fiery red hair trying to burst forth from her roots.
15. Literally Spilling Over Trash
People falling will never not be funny, admit it. Lindsay Lohan falling is never not funny either, no matter how many times we’ve seen it (spoiler alert: A LOT), but something about this spill was funnier than the rest. Maybe because she fell face first into a cactus. Of course it all went down in front of paparazzi who couldn’t wait to catch her face down in the landscaping. You have to appreciate the look of surprise on her face, as if this isn’t the 13,575th time she’s done it.
She very quickly got a hand from the crowd of dudes whose only job it is to escort her around and make sure she doesn’t fall over, but not before making an absolute fool of herself and possibly assaulting a cactus in the process.
14. It’s Johnny Trash
Looking back on how much further LiLo would transform from precocious preteen to tabloid trash, this moment seems pretty mild. Her eyes don’t yet have that half-focused glaze, and both eyebrows are actually planted pretty evenly rather than perked up as if plotting to murder some kittens later in the evening. This was the period in which Lindsay was rolling through L.A. like a human tumbleweed.
Yet, here she was just beginning her journey to trash. You can see it brewing, like a tornado tearing through a landfill somewhere in the farm country of Iowa. It’s coming, and you better get into the cellar if you know what’s good for you, Brandon Davis.
It brings to mind the classic Robert Frost quote: “Two roads diverged in a yellow wood. And sorry I could not travel both.” Nor could Lindsay, as she chose the gravel road that leads straight to the county dump.
13. Driving Miss Trash
Why are you behind the wheel and how is it possible that you haven’t been arrested for DUI so many more times. Thousands of people are killed in the United States by drunk drivers each year and here you are clearly impaired. You can just hear her liver pickling in this photo. Listen harder, can you hear it asking for help?
We don’t know what she looked like earlier in the evening, but it’s probably a safe assumption that this look was nearly as bad when she left the house as it was when she stumbled out of whichever dumpster she was partying in that night. At least she had the forethought to reapply her lipstick before she headed out. You’ve got to look good when you’re on your way to create a four car crash on the streets of Los Angeles, ya know.
12. Definitely Plotting To Kill You Trash
If we had to pick a single moment along Lindsay Lohan’s timeline of trash in which she took the first giant leap toward her trashy transformation, it would be this moment right here. We don’t even know what the hell is happening but that’s OK, she doesn’t either. It’s a fairly safe bet that she wouldn’t know what the hell is happening for at least the next four to ten years to follow.
Maybe this is when her PR team whispered in her ear that a critic said the car in Herbie: Fully Loaded delivered a better performance in the movie than she did. Because she may or may not have been too intoxicated to process that burn, they also wrote it out on the white board behind her using stick figures. Crazy Lohan: Activate!
11. What Happened To Her Grill Trash
We all know drugs can wreck your skin, your teeth, and your life, but what exactly was Lindsay smoking during this tumultuous time? Her teeth went from perfect little white Chiclets to ground-down yellow nubs. It’s like she went to the dentist for veneers but left between the ‘grinding your teeth down’ part and ‘putting the veneers on’ part.
Perhaps she’s really an artist and this was her Yellow Period. From her hair to her teeth to her fingers to her liver, it seemed everything about her during this time was rocking the same jaundiced hue. It’s a shame her teeth ruined this whole look, her hair doesn’t even look that bad. Then again, we don’t have a shot of her leaving this event, presumably because she was picked up in the morning by the garbage truck.
10. Bohemian Trash
Check it out, even the flowers in this picture have given up on life. Lindsay looks like she probably smells a little bit like rat poison and Virginia Slims here, maybe the flowers just couldn’t take it. The longer I stare at them, the more I feel bad for them.
With the right filter and viewed from across the room, this could almost be cute. It was probably the cutest she looked that entire year, anyway. That grimy fringe thing she’s wearing looks like something she stole from Charlize Theron’s wardrobe on the set of Monster but there’s so much to judge here, why focus on the fashion.
9. Ready For My Closeup Now, Mr. Garbage Man Trash
It’s a wonder her eyebrow could even stand upright at this point, but boy did it try. Other eyebrow, maybe you need to lay off the sauce.
You’d think those enviable apple cheeks would distract from the rest of it but nah, we’re focused right on the messiest parts of this. Ironically, she’s wearing a tasteful gold bangle which almost pulls everything together when really she could have slapped on a raver’s entire candy bracelet collection and no one would think wow, that looks terrible. Not any more terrible than she already looks, anyway.
This is the look your friend’s divorced mom would give you when you slept over at their house while she slurped down her glass of wine and it was just as creepy then as it is here. Hey, y’all want some pizza rolls?
8. I Do My Own Makeup Trash
No stranger to the courtroom, Lindsay Lohan has gifted us with all variety of courtroom couture over the years. But nothing quite as dramatic and spectacular as the time she looked like she used actual dirt for blush.
What was the thought process here? Hmm, I’ve been up for two days straight getting my party on and looking a little pale, maybe if I use an ashtray as a compact I can brighten up my look a little. It brings trash to a new level when you’re dressing up your face with literal trash. Just slick back that hair with a little urinal cake gel and you’re ready to go!
This should actually be a thing. Any YouTube makeup artists out there feel like giving us a tutorial on stealing this look? First, fall into some mulch. Then blend. For highlight, you’re going to want a piece of dog crap that’s just turned white. Finish off with old crusty mascara and you’re done!
7. Not Guilty, Your Honor Trash
For all of Lindsay Lohan’s trashy moments — and trust us, we could basically stretch this list out tenfold and still have plenty of trash to choose from — her courtroom trash reigns as some of her finest. Out of all the times she appeared in court, which were many, maybe only twice she looked like she spent more than 15 minutes putting together an outfit. Unless you count the 15 minutes she spent the night before court getting dressed, which no doubt saved time but made it pretty obvious that she took the walk of shame to the courthouse the following day. Oh who are we kidding, every step she took back in those days was one big walk of shame.
Speaking of walking though, if she’d passed you on the street on her way to court that day, you might even think she’s kind of hot with her greasy bedhead and sultry, sleepless stare. Except she was in a courtroom, with a judge and stuff. And she was arguing that she isn’t a danger to society. Look at her. She’s already plotting her next DUI.
6. Gravity-Challenged Trash
The scariest thing about this pic isn’t that it’s Lindsay falling because, hello, it’s Lindsay. It’s so scary because we thought she was over all this tripping over her own feet thing. But nah, she ate it at the Ischia Film Festival in Italy in 2014. Old habits die hard, I guess. Gravity is a cruel mistress.
She eventually got a hand from one of the many men in her vicinity over the years who have made it their duty to peel her up off the floor, and scurried away in embarrassment. You’d think after all these years of falling on her ass she’d have learned how to gracefully get picked up by some random bystander and get on with her day but no, she is somehow still embarrassed by her trademark move.
5. Junkie Chic Trash
Not everyone can rock the platinum blonde look, definitely not someone who looks like they smoke tailpipes rather than Marlboros. Remember that creepy Tan Mom lady who made the rounds on the talk show circuit a few years back? This looks like her tanner, much older sister.
Note to the gingers out there: use SPF 70, don’t live in Los Angeles, and never smoke more than 30 cigarettes a day. If you ignore that advice, you’ll end up looking like Tan Mom’s scary stunt double. Anyone else think it’s funny how her freckles started looking like dirt? It was as if the trash was desperately trying to get out of her pores.
4. West Des Moines Quality Inn Trash
This Olivier Zahm photoshoot for French men’s fashion mag L’Official Hommes should have been unbelievably sexy. What isn’t hot about a redhead rolling around half naked in bed?
Er, well, something about her dead-eyed Come Hither stare was more like Come Hither and give me $10 so I can go re-up from Cletus in the RV outside. If you know what I’m saying. Drugs, I’m saying she was on drugs. Methamphetamine, specifically. The kind brewed in a scummy bathtub by a couple cousins that are also related to each other by marriage, none of that professional-grade stuff.
We wouldn’t be at all surprised if this shoot was done in Breaking Bad‘s Crystal Palace, best known for serving as the office building from which professional skank Wendy performed her hourly duties with married dudes in beat-up rides.
3. Red Carpet Trash
When VH1 gets around to doing the Lindsay Lohan Behind the Music episode, you can guarantee that depressing narrator guy will be speaking over this exact picture saying “at 25, Lindsay began to experiment with drugs and bad hair. This is when things took a turn.” Then her drummer gets in a horrible car crash, someone dies, and in a few years maybe she’s living in Guatemala with half a dozen chickens and a pool boy named Raul.
Next time you’re feeling old, just look at this photo. This is a 25-year-old. Don’t you feel better already? If you squint a little, she actually looks like Owen Wilson playing Anna Nicole Smith in the biopic Night of the Walking Trash. What, you didn’t see that movie?
2. Sisterly Trash
It’s almost not fair to make fun of Lindsay for her various states of drunkenness, but how can we resist when she heads out dressed like the long lost fourth trashy roommate in the Three’s Company house.
The scariest part here is the fear we feel for her sister Ali that she will be thrown up on at any moment. You actually have to wonder if the younger sis who has lived her entire life in her trashy but more successful sister’s shadow is only holding her up at this point in the hopes LiLo will barf all over the paparazzi perched at their feet. It’s almost as if she’s egging her on. Come on, Linds, give ’em the smooch face. Yeah, make it extra ugly, you scene-stealing b-tch. WHY do you get all the attention? Why doesn’t dad love me?
1. Speed The Plow Trash
Right here is where Lindsay was most definitely rising out of the trash heap to be the talented, respectable young lady we all knew she could be back when she was still respectable and young. Sadly, that window closed a long time ago, right around the time she stepped out of a club with her gaudy lipstick smeared across her face and fell right into the gutter. You know, as trash tends to do. She must have been at home there among the empty In-n-Out cups, pieces of paper, and cigarette butts.
Starring in David Mamet’s Speed-the-Plow for the London stage in 2014, Lindsay channeled a recovering alcoholic (oh wait, no, that was actually her) for her role as Karen, a temp secretary with a fondness for ill-fitting suits. And she did OK, according to critics, who were probably waiting anxiously for her to fall over several times and pee on herself at least once.
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