An Annotated History of Lindsay Lohan Nudity

Lindsay Lohan's Playboy issue hits newsstands this week, amid widespread disappointment. Over the last six years, every part of Lindsay has been photographed repeatedly. (Her latest nip slip occurred this morning.) Now presenting Lindsay Lohan: A Portrait of the Starlet as the Sum of Her Private Parts. NSFW after the jump.

Click censored images for NSFW.

June 2004: Debuts Sexiness

An Annotated History of Lindsay Lohan Nudity

Fresh off the success of Mean Girls, LiLo poses in a bikini and high heels, on a rumpled bed with a shirtless man, for Vanity Fair. She is one month shy of her 18th birthday. Before the year ends, she will release her debut single, host the MTV Movie Awards, become Wilmer Valderrama's girlfriend, have her first exhaustion-related hospitalization, have her "first disastrous movie shoot" (Herbie Fully Loaded), and move into the Chateau Marmmont.

Where Her Mind Is: "I think everybody is a drama queen here and there," she tells Diane Sawyer on Good Morning America.

Image via Vanity Fair

March 2006: First Nip Slip

An Annotated History of Lindsay Lohan NudityAt the height of her Nicole Richie/Rachel Zoe-influenced skinny phase, Lohan arrives at a GM fashion show (the catwalk features both models and vehicles) in a skimpy backless dress, displaying sideboob and nipple.

Where Her Mind Is: On body image, to Access Hollywood: "There's a lot of pressure. Especially when you lose a lot of weight and people are telling you, 'You look great!' You are like, 'So, did I look fat before?'"

Click for NSFW via Getty

April 2006: Nickelodeon Ass Slip

An Annotated History of Lindsay Lohan Nudity

Scampering across the stage to receive the award for "Favorite Actress" at Nickelodeon's Kids Choice Awards, Lindsay's tiered mini-dress flips up, revealing a panties-free rump.*

Where Her Mind Is: One month later, Lindsay is nominated for her first Razzie. Oil heir Brandon Davis and a giggling Paris Hilton will invite America to imagine LiLo's "firecrotch."

Click for NSFW via Getty

June 2006: First Nude Photo Shoot

An Annotated History of Lindsay Lohan Nudity

Near the end of her skinny phase—and after a series of career setbacks and rumored drug use—Lindsay appears again in Vanity Fair, in an attempt to clear her name. She goes nude, with strategically placed hands and legs. "It was kind of my idea," she told Entertainment Tonight.

Where Her Mind Is: In the accompanying interview, Lindsay discusses "making myself sick" and using drugs: "I've gotten that out of my system." Later, she will claim that longstanding Vanity Fair writer Evgenia Peretz "misused and misconstrued" her words.

Click for NSFW via Vanity Fair

August 2006: Creepy Bedroom Candids

An Annotated History of Lindsay Lohan Nudity

Perez Hilton publishes creepy pictures of Lindsay undressing in her messy bedroom. (Perez posted back-up here.) The pictures appear to have been taken by a friend.

Where Her Mind Is: A later hack of Lindsay's MySpace will reveal that she suspects Perez is colluding with nemesis Paris Hilton to humiliate her. She confronts Paris in a MySpace message:

FUCK YOU cunt! now that really does make me wonder.... i know u chill with perez, thats a given, ... u guys use eachother like tampons. why didn't he post not 1 article or anything regarding your "stolen storage" stunt? i hate that fat fuck

Image via Perez Hilton

Summer 2006: Boob Bonanza

An Annotated History of Lindsay Lohan Nudity

Paparazzi goes wild. Dozens of nip slips, side boobs, and underboobs. Lindsay learns to use her cleavage for PR announcements: At the height of her boozy trainwreck rumors, she acquires a "Ninety Days" sober chip from Alcoholics Anonymous and affixes it to her right breast before parading by the paparazzi. Later, her publicist admits Lindsay is not sober; the chip is "a tribute to a friend."

Where Her Mind Is: That summer, a letter to Lindsay from a Georgia Rule producer ends up on The Smoking Gun:

We are well aware that your ongoing all night heavy partying is the real reason for your so-called 'exhaustion.'... You have acted like a spoiled child and in so doing have alienated many of your co-workers and endangered the quality of this picture.

Images via Splash

September 6, 2006: Definitive Vagina Photo

An Annotated History of Lindsay Lohan Nudity

Exiting a gondola at the Venice Film Festival, Lindsay's skirt flies up, displaying her entire vulva. It is hairless and pink.

Where Her Mind Is: Lindsay confirms the image's veracity to Elle:

I was rushing through the room, threw the Prada dress on. And that's what happened. And I didn't even see the picture. I don't look at that shit—that's gross. If I wear a dress I have underwear on.

She would disprove that last sentence in a matter of days.

Click for NSFW via Bauer-Griffin

September 12, 2006: Car Crotch

An Annotated History of Lindsay Lohan Nudity

One week after showing her labia majora in Venice, Lindsay shows the majora and minora while getting out of a car in London.

Where Her Mind Is: Later that fall, she will show her vagina once again, this time while getting out of a car in a fur coat in Hollywood.

Click for NSFW

January 2007: 'Exclusive Chanel Event'

An Annotated History of Lindsay Lohan Nudity

After months of focus on her vagina, Lindsay moves the attention back up to her breasts by going braless in a completely see-through dress at a party for "Les Exclusifs de Chanel." Sienna Miller hosts the event, and is forced to pose for pictures next to Lindsay's nipples.

Where Her Mind Is: Months later, Sienna will replace Lindsay opposite Keira Knightley in The Edge of Love. Producers admit to dropping LiLo for "insurance reasons."

Click for NSFW via Getty

March 2007: Zoo Boobs

An Annotated History of Lindsay Lohan Nudity

Bryan Adams photographs Lindsay for German lad mag Zoo. Side boob, under boob, and see-through-top boob are displayed.

Where Her Mind Is: In coming months, Lindsay will check into rehab twice, be arrested for driving under the influence twice, and plead guilty to DUI and misdemeanor cocaine possession once. Her parents will finalize their divorce.

May 2007: I Know Who Killed Me Striptease

Lindsay plays a stripper in famously bad movie I Know Who Killed Me. She performs multiple pole dances and has a long, vigorous sex scene that culminates in a series of orgasmic squeaks.

Where Her Mind Is: For this performance, Lindsay wins her first "Worst Actress" Razzie.

June 2007: Nipple Knife Play

An Annotated History of Lindsay Lohan Nudity

Steamy party photos of Lindsay touching breasts and playing with knives with future Nick Lachey wife Vanessa Minnillo hit the web. Rumor has it the images were stolen off a digital camera in Lindsay's car while she was at lunch at the Ivy.

Where Her Mind Is: "I hate it, like, when these people say, 'Well, why do you go to the Ivy.' Seriously, I like their food! I can't go to a restaurant?"

February 2008: First Naked Marilyn Monroe

An Annotated History of Lindsay Lohan Nudity

Amid "death wish" rumors, Lindsay goes completely naked to recreate Marilyn Monroe's famous "last sitting" portraits for New York magazine. Wearing nothing but a platinum blonde wig, Lindsay poses with sheer handkerchiefs, diamonds, and roses. Her breasts are larger than Marilyn's were.

Where Her Mind Is: "If you saw my house… I have a lot of Marilyn stuff," she tells New York. "It's eerie, because it's this picture of her, and it's kind of cartoony, and there's a big bottle of pills next to her, and they've fallen over." She then segues to a discussion of Heath Ledger.

Click for NSFW via New York

March 2008: Sex Tape Rumor

An Annotated History of Lindsay Lohan Nudity

Still images from a rumored video of Lindsay giving ex-boyfriend Calum Best a blowjob circulate. Despite rumors of a Lohan-Best feud, the world ultimately concludes these are either images of a porn star who resembles LiLo, or some ambiguous video we're never going to see, anyway, so who cares.

Where Her Mind Is: Soon thereafter, Lindsay volunteers to campaign for Barack Obama. The campaign reportedly rejects her.

February 2009: Peekaboo Nipple

An Annotated History of Lindsay Lohan Nudity

Lindsay poses topless for photographer Hedi Slimane with her hair covering her breasts. Her nip slips.

Where Her Mind Is: Around this time, Lindsay is accused of stealing an $11,000 mink coat at a party. "That's bullshit," Lohan says. "That's all bullshit. It was just a misunderstanding." She will eventually be accused of stealing multiple necklaces, a Rolex, Louis Vuitton samples, friends' clothing, and assorted accessories from photo shoots.

Click for NSFW via Hedi Slimane Fashion Diary

April 2009: Topless Tweet

An Annotated History of Lindsay Lohan Nudity

Lindsay discovers the power of microblogging and tweets a hair bra self-portrait.

Where Her Mind Is: Lindsay and Samantha spends the month of April in a messy break-up. SamRo changes her locks and reportedly contemplates a restraining order. They change their Facebook status to "It's Complicated."

Image via @LindsayLohan

October 2009: Topless in the Times

An Annotated History of Lindsay Lohan Nudity

Lindsay is a topless Lolita cuddling a teddy bear in The New York Times' quarterly style magazine.

Where Her Mind Is: Lindsay is preparing for her debut as "artistic advertiser" for Italian fashion house Emanuel Ungaro. Her "disastrous" premiere collection features heart-shaped pasties and sequins. The fashion press is "aghast."

Image via New York Times

January 2010: Hotel Orgy for Muse

An Annotated History of Lindsay Lohan Nudity

A vacant-eyed Lindsay wears a fishnet body stocking and cavorts with an orgy of naked models for a coked-out Muse magazine photo shoot entitled "Lindsay's Private Party." She shows her butt and a boob.

Where Her Mind Is: To keep the momentum going, Muse spends weeks releasing outtakes and behind-the-scenes video of Lindsay making out with models and smoking cigarettes naked in a trashed hotel room.

Click for NSFW via Muse

March 2010: Pee Poses for Purple

An Annotated History of Lindsay Lohan Nudity

Famed pervert photographer Terry Richardson provides Purple with more coke-y looking pictures, many of which show Lindsay pulling down her panties and squatting, as if to pee. In other photos, she rubs her against door frames and wears a crowd of thorns while showing her boobs.

Where Her Mind Is: Harper's Bazaar tries to pin down Lindsay's sexuality: "Would she classify herself as bisexual? 'Maybe. Yeah.' Lesbian? 'No.' She goes on, 'I don't want to classify myself.'"

Image via Purple

April 2010: Suicidal Birthday Suit

An Annotated History of Lindsay Lohan Nudity

Lindsay poses topless with a gun in her mouth and in lingerie in a blood-smeared murder scene for annoying fameball photographer Tyler Shields. This is first of many photo shoots in which Tyler trolls the public by depicting Lindsay and other starlets as the sexy victims of violent crimes. No actual private parts are revealed.

May 2010: Deep Throat Dreams

An Annotated History of Lindsay Lohan Nudity

Lindsay signs on to play Linda Lovelace in the forthcoming Lovelace biopic Inferno. She vows to appear nude for emotionally draining scenes involving "rough sex, sad sex, and sex with a dog." To drum up interest in the film, Lindsay does another Tyler Shields photo shoot.

Where Her Mind Is: After the shoot, Lindsay blows off a probation hearing to party in Cannes, prompting a judge to send her back to jail and further restrict her probation. Inferno's producers fire her while she is bouncing between jail and house arrest. Malin Akerman replaces her in the lead role.

July 2010: Alcohol-Monitoring Ankle Bracelet Nudity

An Annotated History of Lindsay Lohan Nudity

Before reporting to jail for her longest stint behind bars, Lindsay poses topless for German GQ while wearing her SCRAM alcohol-monitoring ankle bracelet. Ambitious German photoshoppers remove LiLo's SCRAM, as well as her belly button. LiLo also poses for SCRAM-obscuring boudoir photo shoots for Maxim and Vanity Fair and a bikini-and-SCRAM photo shoot for the paparazzi. She promises to do nude-with-SCRAM photo shoot to promote her new handbag line, but these photos never materialize.

Where Her Mind Is: The press has resorted to fantasizing about Lindsay getting raped in prison.

Image via German GQ

August 2010: Naked in Machete

Lindsay is in jail, but for the first time in years she is also in a feature film. In Robert Rodriguez Mexploitation movie Machete, Lindsay has a small role as a nun, and is "nude the whole time" she is on screen. She uses stunt nipples, though, and possibly stunt everything-else-s. The mere idea of Lindsay Lohan naked is so strong that it doesn't even matter if it's her body, anymore. At left, the "nudest" scene that uses Lindsay's real body.

Video via Fleshbot

August 2010: Mindfuck Marc Ecko Nudity

An Annotated History of Lindsay Lohan Nudity

A campaign for Marc Ecko's new customizable clothing line also depicts Lindsay nude, but also with a body double. This is meant to be "conceptual" or something.

Where Her Mind Is: At a probation hearing, Lindsay announces she can't afford her court-ordered therapy sessions. She wears $1200 shoes while pleading poverty.

Image via TMZ

May 2011: Braless with the Homeless

An Annotated History of Lindsay Lohan NudityOut of jail and trying (but mostly failing) to meet the conditions of her probation, Lindsay reports to a mandatory community service at a homeless shelter in a see-through top and no bra.

Where Her Mind Is: Fox News panics: "Is Actress Jeopardizing Comeback with Bra-Free Lifestyle?" Lindsay is "no stranger to self destruction," celebrity boob-sag analyst Jo Piazza writes.

Images via Splash

June 2011: Braless Black Swan Wish

An Annotated History of Lindsay Lohan Nudity

Lindsay poses for Plum Miami after the magazine agrees to foot the bill for a luxurious, all-expenses-paid vacation for Lindsay and her entourage. The shoot itself does not feature nudes, but paparazzi shots of the shoot feature nipples and ass. (Bottom left, NSFW here.)

Where Her Mind Is: When LiLo burns Plum Miami by reneging on various promises, the magazine goes nuclear and depicts the starlet screaming "I'm Lindsay Lohan!" at parking lot attendants. She is "indignant" that she was not considered for crazy nude ballerina movie Black Swan.

Images via Plum Miami

June 2011: Visible Boob at Court

An Annotated History of Lindsay Lohan Nudity

During her endless string of court appearances, Lindsay's most conservative outfit—featuring a button-up blouse and black slacks—featured visible boob.

Where Her Mind Is: On her day off, she goes to the beach and another boob pops out.

Image via Getty

July 2011: Clinging to Cleavage

An Annotated History of Lindsay Lohan Nudity

It has been years since Lindsay had a serious job. She has been reduced to a paparazzi avatar, the human sum of private parts made public. Annoying fameball photographer Tyler Shields attempts to say something meaningful about this, but really just wants an excuse to take a picture of someone grabbing LiLo's tit, I think. He releases a series of Lindsay boob grab photos on his website. One photo depicts the photographer giving his subject an eskimo kiss in bed.

Where Her Mind Is: By the end of summer, LiLo is a nightlife fixture, again. She goes on hotel bar crawls and ends up "barely able to walk."

December 2011: Second Naked Marilyn Monroe

An Annotated History of Lindsay Lohan Nudity

Finally, after months of tempestuous court hearings, rumors of bankruptcy, and hours of physical labor at the L.A. County Morgue, Lindsay earns a rumored $1 million to appear in Playboy. She recreates another Marilyn Monroe photo shoot. After years of seeing all of Lindsay's parts contorted in every way imaginable, in high-definition and gritty detail, the resulting pin-up images feel almost prude.

Where Her Mind Is: Lindsay spends her Playboy debut in hiding in Hawaii. She goes to the beach with her sister. Her boob pops out. Again.

An Annotated History of Lindsay Lohan Nudity

* Do you think the Nickelodeon producer who told this ass-centric contortionist to entertain the crowd after LiLo's ass-flashing appearance probably regretted it, in retrospect?

Composite image by Jim Cooke