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Lindsay Lohan Is A Boss Bitch Now. Remember When She Was A Musician?

“Lindsay Lohan has been 18 for just under a week when she tells me her breasts are real. I did not ask (gentlemen never do), though my reporting (discreet visual fact checking, a goodbye hug) seems to confirm her statement.”

So goes the lede of Rolling Stone’s 2004 cover story on Lindsay Lohan.

As a young Rolling Stone subscriber and Mean Girls devotee I remembered this profile, but I didn’t remember how much of it focused on Lohan’s, um, appendages. Reading it as an adult, it feels like a miracle that any of my teen girl idols survived their moment. The early ’00s don’t feel all that long ago, but from this viewpoint those years seem practically primordial. Male journalists could still write like this without being eviscerated on Twitter and Lindsay Lohan’s career as an actor and nascent musician hadn’t yet been eclipsed by … so many things. The previous year, she starred in the remake of Freaky Friday alongside Jamie Lee Curtis, which produced her first single. The next, she played the lead in the iconic coming of age film Mean Girls, which led her to host SNL and made her Hollywood’s preeminent It girl. She did it all without implants! And her star would burn out faster than it rose.

The in-between period is when Lohan’s music career really began. She learned to sing and play guitar in order to appear in Freaky Friday as an apathetic teen named Anna who plays in a band called Pink Slip. They perform two original songs during the film, “Take Me Away” and the Lohan-fronted “Ultimate,” which comes in with a burst of feedback as the credits roll. “Ultimate” is a catchy alt-rock song about finding “the one” (who, in the movie, is played by early ’00s heartthrob Chad Michael Murray) and though it didn’t see widespread success, it was in regular rotation on Radio Disney. The success of “Ultimate” led Lohan to record original songs for her 2004 film Confessions Of A Teenage Drama Queen, which was a total flop but landed Lohan’s voice on the airwaves once again.

Even without “Ultimate,” it was destined. Lohan becoming a singer was the natural trajectory for a Disney kid. Britney Spears, Christina Aguilera, Justin Timberlake, and Raven-Symoné had all transitioned from the Disney Channel to an unprecedented level of teen stardom. Lohan, who came up in Disney movies rather than on TV, was still branded by the corporation. The actor/singer Lohan could most closely be compared to at the time was Lizzie McGuire lead Hilary Duff, who put out her debut non-Christmas album, Metamorphosis, in 2003 and played a burgeoning pop star in The Lizzie McGuire Movie, also released that year.

Duff and Lohan fell on opposite ends of the spectrum. Duff projected a super clean, parent-approved image, while Lohan was quickly corrupted by her newfound fame. She moved to Los Angeles and started going out, a lot. Before she turned 18, Ryan Seacrest asked Lohan whether she’d been going out to clubs as Us Weekly reported. “It’s scary when you’re acting your age and going out with your friends and they’re saying, ‘Oh she’s going out and ordering bottles of vodka at a table,’ and it’s like, I don’t need to do that. Like, I’m cool with Red Bull,” Lohan responded somewhat unconvincingly.

Naturally, Lohan and Duff were enemies. The two publicly fought over Aaron Carter (who else?), who broke off a two-year relationship with Duff in order to date Lohan. “I was dating [Hilary] for like a year and a half, and then I just got a little bored so I went and I started getting to know Lindsay,” Carter, er, deftly explained to CNBC. The feud unfolded from there, and it involved the aforementioned Murray, Joel Madden, and an SNL skit. It ended in 2007 when Duff said of Lindsay: “She’s a nice girl.”

Lohan always came across as exceedingly likeable in interviews, but she wasn’t as good at keeping in line with the Disney image as her peers. She never wore a purity ring and her music defied the saccharine aesthetic Disney stars were expected to maintain. Much like “Ultimate,” Lohan’s debut Speak is a collection of hard-rocking pop songs in the vein of contemporaries like Lohan’s sort-of rival Ashlee Simpson, Kelly Clarkson, or Avril Lavigne. Lead single “Rumors” directly referenced the paparrazi that brutally hounded Lohan when she started living in LA: “I can tell that you’re watching me/ And you’re probably gonna write what you didn’t see/ Well I just need a little space to breathe/ Can you please respect my privacy.”

Lohan sang “Rumors” during her first live televised musical performance on Good Morning America and looked like a natural. She exuded the confidence that comes with being on the rise, in spite of telling Diane Sawyer that she is self-critical because music felt like a direct reflection of her real personality, whereas acting felt like facade. “Sometimes I don’t like the way I look, sometimes I do,” she said. “It’s weird to see myself singing though, it’s a dream come true. It’s my second passion.”

There is no question that music was Lohan’s second passion. While Speak is a perfectly competent pop album, there is nothing about it that might be considered memorable. The writing for it began as early as 2001 when Emilio Estefan Jr. and Gloria Estefan signed Lohan to Casablanca Records. She worked with Diane Warren and Randy Jackson on some music that ultimately didn’t make the cut, though the Warren-penned “I Decide” landed on the soundtrack to The Princess Diaries 2: Royal Engagement. The list of composers and producers involved in Speak is quite long and included some impressive names for the time. Cheiron Studios’ Andreas Carlsson worked on some songs as did Grammy-nominated songwriter Kara DioGuardi. Other writers included David Eriksen (Sheryl Crow, Jessica Simpson), Carl Falk (Ariana Grande, Demi Lovato, One Direction), Sevan Kotecha (Usher, Britney Spears, Hilary Duff), and more.

Lohan’s voice was always one of her defining features. It is instantly recognizable, and it was well-suited for a rock-oriented pop album, but the songs on Speak are often overstuffed tongue-twisters. Take the title track, which suffers from a very unique case of having way too many words in it. “Everybody’s got a point of view/ And the right to their own opinion/ So don’t be scared of what I’m gonna do/ When you let me know your intuition,” is sung in all of about two breaths.

The cover of Speak kind of looks like something Lohan’s Freaky Friday character Anna would scribble in the margins of her notebook, or a page in Mean Girls’ infamous Burn Book. Her sophomore album, A Little More Personal (Raw), was released only a year later and it shed that mallpunk image. She posed topless with her back to the audience for the cover, trying on the role of a vixen rather than the misfit in the back of English class. The songs are quite different, too, as one might anticipate from the title. A Little More Personal (Raw) still has a bit of an edge but it’s eclipsed by a bleak darkness that feels absent from Speak, which makes sense, given how chaotic Lohan’s personal life was at the time.

Her family, though never perfect, was on the brink of total meltdown. The year A Little More Personal (Raw) debuted, Lohan’s mother Dina (who was also her manager) filed for divorce from her father. Michael Lohan has been a notorious fixture throughout Lohan’s career. He went to prison for tax fraud when Lohan was a teenager, struggled with alcohol and drug addiction, and allegedly abused his wife in front of Lohan and her younger siblings. Though Lohan had dismissed her father’s issues in 2004 — saying he was a “big boy” who could handle his troubles — by 2005 the situation overtook tabloids. And, one would assume, Lohan’s entire life.

A Little More Personal (Raw)‘s opening track is called “Confessions Of A Broken Heart (Daughter To Father).” It is the only song Lohan has ever released that made it to the Billboard Hot 100, peaking at #57. It’s also revealing for a celebrity, even one whose life was on near-constant display in the media. “Daughter to father, daughter to father/ Tell me the truth, did you ever love me?” Lohan screams on the chorus, and it might be the best example of how capacious her voice actually was. In a sense, A Little More Personal (Raw) was Lohan’s attempt to work through a festering childhood trauma, which is explored further in the video.

“Confessions Of A Broken Heart (Daughter To Father)” is the strongest song on an album that integrates an erratic number of influences, culminating in something that isn’t wholly unlistenable but absolutely belongs in 2005. There’s a cover of Stevie Nicks’ “Edge Of Seventeen” that, while not bad, brings nothing new to the standalone classic. There’s also a cover of Cheap Trick’s “I Want You To Want Me,” which kind of just sounds like Cheap Trick sung by Lindsay Lohan. (Letters To Cleo covered the song for Ten Things I Hate About You, so maybe that yielded Lohan’s version.) The album also features another pretty OK song called “My Innocence,” which is kind of about virginity but mostly about feeling used up and exploited by industry snakes.

Critical reception of A Little More Personal (Raw) was lukewarm and Lohan never toured the album, though she did perform a medley of “Confessions Of A Broken Heart (Daughter To Father)” and “Edge Of Seventeen” at the 2005 American Music Awards. Two years later, her struggles with substance abuse sent her to various rehabilitation facilities and eventually jail. She was sentenced to three years probation, which she violated in 2009. In the interim, Lohan signed to Universal Motown and was working on a third album that was eventually scrapped, though several tracks would leak in 2010. She did release one single in 2009 called “Bossy,” and it abandons the rocker image she curated on her first two albums. The song is clubby and generic, and it hit #1 on Billboard’s dance chart. “I’m just a little bossy/ I like it how I like it when I like it and that’s how it is,” the chorus goes. It’s a  projection of control, a state Lohan clearly wasn’t in at the time of its recording.

A decade, a move abroad, a public reckoning facilitated by Oprah, and many, many, many controversies later, Lohan is back in the spotlight. Her new reality show, Lindsay Lohan’s Beach Club, premiered on MTV earlier this week, and it follows Lohan as she runs a beachside club in Mykonos, Greece. (Being a businesswoman is Lohan’s third passion.) She chose this particular beach because it is the same one where her then-fiancé Egor Tarabasov was filmed assaulting her. “And that’s why I’m here today, because it was on that beach where I got hit. I said, ‘You know what? If there’s anything I can do, I’m going to get that beach. It’s going to be my beach,'” Lohan told The New York Times.

Lindsay Lohan’s Beach Club is being billed as a reclamation of both Lohan’s personal life and professional image. Contradicting that narrative is the simple fact that it is a reality show. Lohan’s tagline throughout is “Boss Bitch” and the opening credits roll to “Bossy.” No one has thought of that song in a decade, but in the days since the show premiered, Lohan has hinted that she may collaborate on new music with her sister Aliana. Ratings have been good, but those who tuned in to witness some truly certifiable Lohan drama are disappointed because Lohan (unlike her closest reality TV counterpart, Lisa Vanderpump of Vanderpump Rules) is exceedingly awkward in the role of the mother hen. Further troubling the narrative is the fact that Lohan recently livestreamed herself attempting to help/kidnap a homeless woman’s children in Moscow, which led some to question her hard-fought sobriety and worry about her overall mental health.

In the years since Mean Girls and Speak, Lohan’s public image has undergone a series of transformations spurred on by rehabilitation. There isn’t a moment in her career beyond 2004 that wasn’t somehow colored by something reported in the tabloids, the increasingly media-thirsty and cruel behavior of her father, and the overwhelming sense that Lohan was being suffocated by her own mythology. Though none of her songs have transcended the 2000s, Speak and A Little More Personal (Raw) still sound like the enthusiastic, though perhaps slightly misguided, work of a teenager excited to do something new, to push her talents in another direction. And, in a sense, the latter was an early attempt for Lohan to take back her narrative. Her songs couldn’t compete in the booming teen pop landscape, but I’d like to think that she got at least a tiny bit of joy out of making an album that, to her, felt “a little more personal” than the media narrative that chased her.

In 2010 — six years after a Rolling Stone writer fixated on a brighter-eyed, 18-year-old Lohan’s body, five years after her last album, and nine years before her latest attempt at a comeback — Vanity Fair published a cover story on Lohan simply titled “Adrift …” In 2004, the biggest scandal about Lohan was questioning the authenticity of her breasts; the Vanity Fair profile was reported in the weeks before and after Lohan went to jail for violating the terms of her probation. In the piece, Lohan is photographed on the deck of the Sovereign, a boat built for Judy Garland in 1961. It couldn’t have been coincidence, and it’s stomach-churning to think of the art department’s logic behind it: “Here’s a young starlet on the brink of total self-destruction. Let’s put her in Judy Garland’s shadow.”