Lindsay Lohan was easily one of the most capable up-and-coming actors of her generation. As we watched her grow-up on-screen, our level of appreciation of her skills grew... until it didn't. And that was a sad time for all of her fans. But before her highly publicized fall from grace, Lohan showed a tremendous amount of seemingly natural abilities. As a child actor, she was highly capable of being both charmingly funny and a notable dramatic thespian. As she grew older, we saw a more versatile performer in her. She was naturally attractive which helped sell her skills as a Mean Girl, and yet she could be the girl-next-door who was simply trying to navigate life. But, of course, all of this changed and her life as a film star came to an end. But we can't entirely blame her. She seemed to have had a challenging upbringing.
Still, it's enjoyable to look back on the days when things appeared to be slightly less dramatic for Lindsay Lohan. That's why we've compiled a list of some of the greatest photos of her upbringing in the Lohan family, her early social life, as well as the first few times she captured our attention on the big screen. Without further ado, here are 25 Photos of Lindsay Growing Up.
25 A Holly Jolly Christmas
It's hard not to appreciate this beautiful Christmas photo. After all, it seems like little Lindsay Lohan is as happy as a clam. The photo also depicts her sibling, and mother Dina Lohan. At this point, it appears that Lindsay and her mother had a very positive relationship before stardom came between them. Of course, we can only assume what actually has gone down between them.
This Christmas photo seems like any of the Christmas photos that we have in our own family collection. Therefore, it allows us to relate to this kid before she became one of the biggest celebrities of all time.
24 Mother and Child
Whether it’s by seeing some of Dina Lohan’s public actions, or how the press has covered them, it's quite easy to think that this is a mother that most children wouldn’t want to have. However, we have absolutely no idea what the true relationship between Dina Lohan and her famous daughter, Lindsay, truly is. But we can appreciate the bond between mother and daughter in the photographs from Lindsay’s past. Although this photo may not be one of them. Hilariously, both mother and daughter don't particularly look like they want to be there.
23 A Star Is Born
The Parent Trap was Lindsay Lohan’s big break. She had done a couple of T.V. series but it was her very first film. Not only that, but she played two characters incredibly efficiently. Both of whom showed heart and great senses of humor. The Parent Trap made Lohan an actor. But she truly became a star when she stepped out on to the red carpet at the LA Premiere, featured here.
We can see glimpses of the megastar that she would become in this very photo. Although she seems somewhat timid, behind her eyes dwells a far more driven young woman.
22 Two Bright And Shining Stars
It's difficult not to feel a little sadness when looking at this photo of Lindsay Lohan and Amanda Bynes. It was taken at the Nickelodeon Kids’ Choice Awards long before both of their public falls from grace. It's sad because both young women had immense talent. They both started their film and television legacies quite young. Both managed to star in several shows and films that showed off their comedic and dramatic abilities. It's somewhat ironic that the two young women look so happy and wholesome in this photo when just a few years after it was taken things would change quite significantly.
21 Growing Up In Front Of The Camera
Of all the photos on this list, this one shows off just how comfortable Lindsay Lohan looks in front of the camera. This is impressive given the fact that The Parent Trap was her very first film. Although she's in the middle of a take, and thus in character, she seems truly at ease. But this is probably because she spent almost her entire young life growing up in front of the camera whether she was modeling or shooting television shows and movies.
20 On-Screen Mom
For better or for worse Lindsay Lohan received a great deal of surrogate parenting through the mother characters in her films. Of course, this didn't replace Dina Lohan's job as Lindsay’s actual mom, but it must have given Lindsay an interesting opportunity for contrast and comparison.
This image is taken from the set of one of Lindsay Lohan’s most famous and beloved films, Mean Girls. It features Lindsay and Ana Gasteyer who played her mother in the film. The pair seems to be getting along well between takes.
19 The Casual Celebrity
It's truly amazing to see the style of the early 2000s when this photo was taken. Lindsay appears to be on a red carpet at some sort of movie premiere. It could be for one of her films or it could be for someone else's. After all, she was a big enough star, at the time, to be invited to several different premieres. Regardless, she seems incredibly casual in this photo. But that's the style that she was going for. The camouflage pants and the colored lenses of her glasses are totally what was fashionable at the time that this photo was taken.
18 Family Life In The Spotlight
If someone who knew nothing about the Lohan family looked at this photo, they’d probably think that these three were incredibly happy. Unfortunately, due to their press, we’ve learned that their history has been a tad more complicated. But that's to be expected since all three of the people depicted in this photograph spent a lot of time in the spotlight.
Lindsay, of course, was in the spotlight because her parents encouraged her to become a star. Michael and Dina Lohan, on the other hand, seemed to have taken their daughter’s spotlight in less than productive ways. We hope that there’s more happiness behind this photo than those in the know may believe.
17 The Trio Of Trouble
In 2006, the paparazzi photographed Lindsay Lohan alongside Britney Spears and Paris Hilton after the three of them spent the night partying. At the time, each of them was heavily in the spotlight and essentially three of the biggest celebrities on the planet. It wasn’t long after this photograph that both Britney and Lindsey had their very public meltdowns. This photograph captures a friendship that may not have added much positivity or maturity to any of these women's lives. Still, it’s incredible to see the three of them together like this.
16 Smiling Face On The Red Carpet
This photograph was taken at the 2002 premiere of Austin Powers in Goldmember. It was still a time when Lindsay Lohan was a well-liked and a reliable movie star. As we can see from this photo, she seems very comfortable and happy with her position. It's too bad that in the following years she would lose the positive stature that she earned for herself. We can also see that she had not been taking part in activities that wore away at her natural beauty. At this point in time, she still looked fresh face and healthy.
15 Back In 2006
In this photo, Lindsay and her mother Dina Lohan are at a public event. At the time that this shot was taken, both had already been going through some public conflicts. Additionally, we can already see the difference in Lindsay’s appearance in comparison to some of the earlier and younger photos of her. Nonetheless, she’s still included at public functions and not yet experiencing her most unfortunate days. It's also nice to see the two women getting along and finding something to connect over.
14 Young And Fresh-Faced
This photo was taken on the set of The Parent Trap. In comparison to the previous photo on this list, as well as the one of her and Britney Spears and Paris Hilton, the level of purity shown here is astounding. Honestly, she looks just like any other young woman of her age group. Granted, she is on the set of a major Hollywood movie. Once again, we can see how comfortable she appears in front of the camera this is it right that will do her well in the years following the taking of this photograph.
13 Get A Clue
After The Parent Trap, Lindsay’s next big project with a TV movie entitled “Get A Clue”. In the movie, she starred alongside Suite Life of Zack and Cody star Brenda Song. The film told the story of a wealthy student who investigates after one of your teachers goes missing. This photo is taken on the set of this movie. As we can see, Lindsay has grown up a little bit since the movie that made her desirable actor. However, there’s little difference in confidence Lindsay clearly had a level of comparability while being on screen.
12 Growing Up Fast
Lindsay Lohan signed with Ford Models long before she made her film and television debuts. Her parents signed her up for this regardless of whether she wanted it. However, she thrived at the job. This photograph shows us just how natural of a model she truly is. It was taken not long after The Parent Trap which means that Lindsay was young. Lastly, we can see from the makeup and hair that she appears to be a lot older than she was. Essentially, this is a young woman who never really saw her childhood.
11 Baby Lindsay
This could be a photo of any of us. After all, chances are, we have pictures of ourselves as babies with food on her faces and smiling widely. But really this is that this is one of the biggest stars on the planet. Only this was a star before she became one. Yes, this is the earliest photo we have on this list of Lindsay Lohan. In fact, it may be one of the earliest photos of Lindsey on the entire Internet. Needless to say, Lindsay appears like any other young happy and healthy infant. It's amazing to think that this baby would go on such a rollercoaster of my life.
10 Appearing In Teen People
This photo was taken of Lindsay during her teenage years. It was before she truly started getting into trouble. But that’s easy to tell since she seems so young, healthy, and naturally beautiful. At this time, she was doing several different Disney movies and was often featured in magazines such as this one from Teen People. That one person who received so much attention and adulation would be pushed to grow up fast. Then again, few of us wouldn’t enjoy being featured in a great photograph such as this one.
9 Life As A Child Model
As mentioned earlier, Lindsay was a model before she ever became an actor. This is fairly typical for up and coming young stars. Usually, they need to be noticed by people in high places before they are asked to audition for a big budget project such as The Parent Trap. Young models like Lindsay were used to sell clothing to kids around her age as we can see from this photograph. If you look into her eyes, there’s a real sense of maturity that shouldn't be present at this age. That's probably because she was encouraged to start a career before the age of ten.
8 Working Alongside Legends
One of the benefits of being Lindsay Lohan is the fact that she got to meet and work with some of the great film and television legends of all time. Of course, she got to work with the likes of Tina Fey, Amy Poehler, and Dennis Quaid. But she also starred alongside Halloween's Jamie Lee Curtis in Freaky Friday.
This photograph was taken at the premiere of the well-liked Hollywood remake. Although the pair had been working together for months before this, they appear somewhat comfortable with one another. Clearly, it went okay.
7 Boyfriend In The Spotlight
Nowadays, we are mostly concerned with the dating lives of celebrities like the Jenners, Kardashians, Drake, and Ariana Grande. But back in 2003, it was all about the love triangle that existed between Lindsay Lohan, Hillary Duff, and Aaron Carter. The three of them were a young person's Brad, Angie, and Jennifer.
This photograph shows how public Lindsay's fling with Aaron was. Of course, the press seemed to side with Hillary, but Lindsay got the sharp-end of the stick not long after this image was taken. Still, the pair appears somewhat comfortable with one another.
6 Showing Off For The Camera
Unlike an earlier photo of Lindsay as a child model, this one actually looks like she's acting her age. Of course, not all modeling is meant to be taken 100% seriously, but Lindsay is definitely hamming it up for the camera here. She seems to be enjoying herself, even though she's at work. This is the type of energy that probably helped her get her first big-screen role in The Parent Trap. After all, it feels like she's a total natural.
5 Lindsay And Tyra
Just after The Parent Trap, Lindsay starred in a T.V. movie alongside Tyra Banks herself. This image is taken from the set of this film. It was called Life-Size and was part of The Wonderful World of Disney films. The movie was about a widower's daughter who tries to bring her mother back to life but ends up making her doll come alive instead.
We can see that Lindsay was clearly a force to be reckoned with at this time. Even top-models like Tyra Banks wanted to work with her after Lindsay's debut in The Parent Trap.
4 The Young Starlet
This image features an 11-year-old Lindsay who truly appears as confident and mature as a thirty-year-old. It was taken on the set of The Parent Trap where Lindsay experienced true stardom for the very first time. Heck, she even got her very own director's chair.
The photo shows us a young woman with her entire life ahead of her. A few better decisions and things could have gone in a completely different direction. Perhaps a direction more in-line with this fabulous photo of her.
3 On The Set With Allison Pill
After Freaky Friday, Lindsay's next big movie was about a teenager who is convinced her entire life revolves around her until she is pushed to move to a small suburban community that has her competing for attention. As we can see from this photo from the film, Lindsay is older and preparing herself for more adult projects.
The film also starred Allison Pill (The Newsroom and Vice), who is pictured here on set with Lindsay. Both these young women started their jobs quite early on in life and that's probably why they seem so comfortable in front of the camera.
2 Seeing Double
Most young actors only hope for a role in a Hollywood movie, but Lindsay won two for her first feature, The Parent Trap. As we can see here, Lindsay played both long-lost twin-sisters in the film. In order to do this, the filmmakers had to use a body double. The face of the double was edited out and Lindsay's face was placed over it thanks to the magic of CGI. In this photo, it all looks seamless. It almost appears as if there are actually two Lindsay Lohans.
1 Turning Point Stuck In The Road
As we can see in this photo, Lindsay traded in her iconic red hair for a more platinum look. Of course, this was followed by other hairstyles including turning it brunette. But some believe that the change from red to blonde signified a larger change. No longer did she want to be seen as the cute ginger from those Disney films. Unfortunately, these changes were made worse by the presence of her parents. However, we can never truly know what went on between them. At least here they appear to be quite happy.