--- title: "19 Photos of Lindsay Lohan's Rollercoaster Life ..." description: "January 2006; March 2006; August 2006; December 2006; January 2007; More ..." url: "https://allwomenstalk.com/19-photos-of-lindsay-lohans-rollercoaster-life/" category: "celebs" last_updated: "2026-06-07" --- # 19 Photos of Lindsay Lohan's Rollercoaster Life ... Remember The Parent Trap and little Lindsay Lohan who looked so full of potential? Remember when we thought she would grow up into an actress who would contribute so much to the world of films? Well, okay, you may not have thought that but I certainly did. There was something about the freckled bubbly actress that just seemed fun to watch. Up until Freaky Friday. After that, well...these photos will explain: ## 1. January 2006 _ So this would be a first of too many Marilyn Monroe-inspired photo shoots_. ## 2. March 2006 ![March 2006](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/22_350x263.jpg) This was taken right around the release of her movie with Meryl Streep, The Praire Home Companion. Around this time, her life still seemed like it would follow the right path. Sure she was already a paparazzi favorite for her partying and underage drinking but they only looked like[parts of a normal teenager's life](https://goo.gl/XLxqxT). ## 3. August 2006 ![August 2006](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/31_350x275.jpg) Only a few days after claiming that she's cleaning up her act, she [partied](https://www.popsugar.com/celebrity/LL-Cant-Hyde-22219). ## 4. December 2006 ![December 2006](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/41_350x270.jpg) Poor girl. Someone [should have helped her](https://goo.gl/nnlmvX) then, huh? At around this time, she had admitted that she has been going to Alcoholics Anonymous for about a year. ## 5. January 2007 ![January 2007](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/51_350x270.jpg) With mom Dina's help, Lindsay enters rehab. But she did look like [she was enjoying it too much](https://web.archive.org/web/https://www.popsugar.com/114182) and her being famous did not sit well on the other patients. ## 6. May 2007 ![May 2007](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/61_300x300.jpg) She sounded and [looked normal](https://goo.gl/VncvcC)here. But by this time, she already entered rehab and had photos of her snorting cocaine and doing everything your mom would never imagine. This seemingly perfect girl was just another act for our dear Lindsay, perhaps? ## 7. July 2007 ![July 2007](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/71_300x322.jpg) [Busted for DUI for the second time](https://web.archive.org/web/http://www.popbytes.com/archive/2007/07/oh_my_word_lindsay_lohan_busted_again_for_dui.shtml). Headed to rehab once again. ## 8. October 2007 ![October 2007](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/81_300x300.jpg) [Out of rehab and back in her dad's life](https://goo.gl/TIw7tR). If only this lasted. ## 9. February 2008 ![February 2008](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/91_293x402.jpg) "What was I thinking?" she said when asked [about the crazy year she had](https://goo.gl/5ZnO72). Then did [another Marilyn Monroe-inspired shoot](https://goo.gl/NYCizp). Tsk tsk tsk. ## 10. March 2008 ![March 2008](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/101_300x300.jpg) Finally, something that seemed like a break for this actress -- [a line of leggings.](https://goo.gl/rXTYKD) ## 11. June 2008 ![June 2008](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/112_350x606.jpg) Happy with a new love (Samantha Ronson) and making films again, [Lindsay looked healthy](https://pinkisthenewblog.com/the-new-kid-on-the-block-everything-you-need-to-know-about-cbd/). ## 12. January 2009 ![January 2009](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/121_350x350.jpg) [One year with Samantha](https://pinkisthenewblog.com/4-super-simple-steps-to-make-2020-your-year/). A year of crazy dad-daughter public fights, getting too skinny, partying again. ## 13. May 2009 ![May 2009](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/131_275x313.jpg) [Again with the Marilyn Monroe](https://goo.gl/I2H3pD)? At this point, things have gone south with her relationship with Samantha. ## 14. June 2009 ![June 2009](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/141_350x264.jpg) Celebrated 23rd year and back with Samantha. [Life is good again](https://www.popsugar.com/celebrity/Photos-Lindsay-Lohan-Celebrating-Her-Birthday-Bikinis-Las-Vegas-3393702), yes? Of course, this did not last long. ## 15. August 2009 ![August 2009](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/151_350x233.jpg) [Reunited](https://www.popsugar.com/celebrity/Photos-Britney-Spears-Lindsay-Lohan-Out-LA-Together-3749889) with an old friend and fellow party girl. Lindsay looking too thin again. ## 16. October 2009 ![October 2009](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/161_350x312.jpg) Let's dub this the [Paris Fashion Week 2009 Disaster](https://www.popsugar.com/celebrity/Photos-Lindsay-Lohan-Paris-Ungaro-Runway-Show-5435146). Poor Lindsay. She was given an office at the Ungaro fashion house but all that she could come up with was heart-shaped nipple pasties? ## 17. October 2009 ![October 2009](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/171_350x266.jpg) For violating the terms of her probation, Lindsay was[sentenced another year](https://www.popsugar.com/celebrity/Photos-Lindsay-Lohan-Arriving-LA-Courthouse-5677083). But seriously, why does her forehead look like that? Why does she look 50? ## 18. October 2009 ![October 2009](https://resize.allw.mn/1028x0/filters:format(webp)/filters:quality(70)/content/www/2009/11/181_300x300.jpg) Okay, I just posted this photo so that you can compare her to her June 2008 self. [Scary transformation](https://goo.gl/MLXFgv), right? ## 19. November 2009 _ Doing what she does best - partying_. ## Related Posts - [Hollywood March Madness: Lohan V. Moss, Rosie V. 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