For those of us who spent countless hours browsing blogs or picking up tabloids in the 00s, there was always that one It Girl we adored. Don’t get me wrong—I loved all of them, from Nicole Richie’s infamous skinny Memorial Day email to LC’s drama at Le Deux. Or maybe you were drawn to someone a bit more niche, like Alexis Neiers and Tess Taylor from the notorious Bling Ring.
But for me, it was always Lindsay Lohan. That was my girl. I thought she was the coolest, hottest, messiest bitch on the planet. I’m not quite sure if it was the undeniable lesbian behavior, the constant gaslighting of the paparazzi (“I never said that, Paris is my friend”), or maybe it was that I found some relatability in the chaos of Dina and Michael. And while I love a poor little rich girl that tends to be a bit of a history revisionist like Paris Hilton, I think there’s something really admirable about Lindsay being far more self-made.
Whatever the case, Lindsay was that girl, and in my humble opinion, her music career is one of the most overlooked and underappreciated of the era. I’d also argue that this album was the harbinger for the absolute celebrity chaos that we were about to experience. So let’s get nostalgic and revisit one of Lilo’s many talents: her discography.
The Rise of Lindsay, the Pop Star
Similar to her rival Hilary Duff, we first got a glimpse of Lindsay’s music career through Disney—first with her 2003 song “Ultimate” for the Freaky Friday soundtrack, and then in 2004 with “Drama Queen (That Girl)” off the Confessions of a Teenage Drama Queen soundtrack. But before these soundtrack singles, she had already signed a five-album contract in 2002 with Emilio Estefan Jr. (yes, Gloria Estefan’s husband). However, the deal was later scrapped for unknown reasons.
Two years later, in 2004, Lohan signed with Casablanca Records under the management of Satan himself, Tommy Mottola. Yes, the same Tommy Mottola who abused and controlled Mariah Carey.
During production, the album and the film Herbie: Fully Loaded were halted on October 21, 2004, when Lohan was rushed to Cedars-Sinai Medical Center, reportedly for exhaustion (long before the days of the celebrity Lyme disease coverup) and a high fever of 103 degrees. Lohan ended up having a kidney infection and was also in the middle of a family crisis when her father, Michael, was arrested earlier that year. After staying in the hospital for six days, Lohan was released and returned to set to finish filming the movie and recording her album. At this time, she was also scheduled to appear in a cameo role for That ’70s Show, allegedly playing then-boyfriend and known weirdo Wilmer Valderrama’s love interest. I’d argue it’s best that never happened.
Under Casablanca, LiLo went on to release two albums: Speak in 2004 and A Little More Personal (Raw) in 2005. Speak, released just seven months after Mean Girls hit theaters, received mixed reviews—as did anything a woman dared to do in 2004. But despite the criticism, it debuted at an impressive No. 4 on the Billboard 200, selling 261,762 copies in its first week. It eventually went Platinum in the U.S., signifying over one million copies sold.
Paparazzi, Partying, and Platinum Records
At the time of Speak’s release in 2004, Lohan was at the top of her career, but things were starting to show some cracks. Earlier in the year, Duff had starred in Confessions of a Teenage Drama Queen; in May, Lohan appeared on SNL in the now-notorious Debbie Downer at Disney World skit, and—my personal favorite—Hermione Returns to Hogwarts After A Growth Spurt.
At just 18, Lohan was coming into her career. However, by the end of 2004, early signs of tabloid scrutiny began to emerge, particularly with rumors of feuds (especially with Hilary Duff over Aaron Carter) and discussions about her rapid weight loss.
Speak’s lead single, “Rumors,” was a direct reflection of Lindsay’s life at the time—an anthem about her experiences with the paparazzi and relentless tabloid culture. I’d argue that Rumors is her most commercially recognized song, though by no means a Billboard hit. Its cultural impact, however, was undeniable. This was peak 2000s, when the obsession with celebrity culture, paparazzi harassment, and blog-fueled discourse ruled everything. At the time, there weren’t many accessible critiques of the media machine, so Rumors felt like one of the only mainstream pieces of pop commentary on fame’s dark side.
The second single, “Over,” was my personal favorite. The song chronicles an on-again, off-again relationship, and the music video leaned heavily into dramatic and complicated imagery. Lindsay’s character falls for a boy whose abusive father forbids their relationship—a dynamic that, in retrospect, feels very telling. Over was one of her more successful releases, peaking at No. 1 on Billboard’s Hot 100 chart for three weeks.
Then there’s “First,” Speak’s other single—if we can even call it that, considering it was mostly known as the title track for Herbie: Fully Loaded (2005). This song alone is incredibly chaotic, and I’d argue it was a crucial domino in the public tabloid downfall of LiLo. If you don’t recall, Lindsay allegedly stormed out of the Herbie: Fully Loaded premiere because First wasn’t played during the main race sequence and was instead relegated to the end credits. And as a Lindsay apologist, I get it. If I had to do goofy-ass Disney movies, I’d also want my song played in a prime cinematic moment.
It’s also important to note that this incident happened during her blonde era, so naturally, dark-sided energy was afoot.
Anyway, First is great.
Speak and Its Place in 2000s Pop Culture
Speak is an interesting chapter in millennial pop. It predated other celebrity albums like Paris Hilton’s Paris (2006) and Heidi Montag’s Superficial (2010) but, in my opinion, was just as edgy as the pop-punk girlies of the time—think Ashlee Simpson’s Autobiography (2004) and Avril Lavigne’s Let Go (2002).
It was also released during a fascinating time for women in rock. Le Tigre had just dropped This Island, The Gossip was making waves in indie spaces, and all of this was happening roughly a decade after the riot grrrl movement. While Lindsay went the pop route, there was an edge to her—something more complicated. Speak focused on the perils of fame and identity, making it deeply relatable, even though it came from someone who had anything but a regular childhood.
I won’t bother drawing comparisons to Hilary Duff’s 2003 Metamorphosis (though the discourse is there), but Speak resonated with young millennials navigating complicated home lives and identity struggles. It wasn’t just pop fluff—it had angst, glamorously aspirational drama, and it had the voice of a girl who had already seen too much.
Things Get Raw
Less than a year after Speak, in November 2005, Lindsay Lohan released A Little More Personal (Raw), which housed my personal favorite Lindsay song—one for the girls with daddy issues—“Confessions of a Broken Heart (Daughter to Father).” While only a year apart, the two albums—and the state of Lindsay’s public perception—could not have been more different.
After wrapping up her ill-fated film Just My Luck, Lindsay began writing and recording her second album. “I've been writing a lot, almost every night,” she said at the time. “There's been a lot going on in my life lately, and I think people can find that escape in hobbies that they do. I don't do yoga or anything, but some people use that. Everyone has their own thing, and I use writing.”
So what was happening in her life at the time? Well, at the end of 2004, during the press cycle for her first album, she split with boyfriend Wilmer Valderrama (allegedly due to his involvement with Ashlee Simpson, which Ashlee denied in her 2005 song “Boyfriend”). Rumors of her eating disorder were also picking up steam. But what I think was perhaps most difficult were the actions of her parents, who had quickly become tabloid fixtures in their own right.
In January 2005, Michael and Dina Lohan separated again after years of contentious fighting. Michael Lohan was soon charged with attempted assault after a family dispute. While awaiting sentencing, he was involved in a car accident that led to additional charges of DUI and aggravated unlicensed operation of a motor vehicle. So yeah, safe to say Lindsay was going through it—all while working non-stop.
Public perception of Lindsay was complicated and, honestly, unkind. A lot of people were beginning to see the writing on the wall, but rather than acknowledging the obvious turbulence in her life, much of the media dismissed her behavior as bratty. Reports of her family issues and alleged unprofessionalism started to overshadow her actual work. She was frequently photographed partying at LA hotspots like Teddy’s at the Roosevelt Hotel, and whispers of trouble with Disney executives grew louder. I’d argue that 2005 was the last year where Lindsay’s work could be discussed in a standalone way—without being overshadowed by her personal life.
With all of that in mind, I’d say Lindsay’s best performance of all time took place during this record cycle—at the 2005 American Music Awards. The performance featured a medley of “Confessions of a Broken Heart” and “Edge of Seventeen”. It was met with less-than-kind reception, but babe, it wasn’t for the critics. It was for us, the pop culture girls. Critics slammed her for shaky vocals and accused her of being overly dramatic, but let’s be real—this was high camp. Fucking haters.
A Little More Personal, A Lot More Criticism
Similar to her AMA performance, A Little More Personal (Raw) received mixed reviews—though the criticism felt harsher than it had for Speak. Some called the album a calculated attempt at emotional vulnerability for the sake of commercial appeal. Brian Hiatt of Rolling Stone wrote that Lindsay “makes a fatal mistake on her second album: She tries to, like, express herself.” Interesting reaction. Almost as if critics weren’t evaluating the music itself but rather using the album as an excuse to take shots at an 18-year-old girl with family trauma. Because let’s be honest—thats what sold magazines.
Commercially, A Little More Personal (Raw) debuted at No. 20 on the US Billboard 200, selling 82,000 copies in its first week. The album’s first single, “Confessions of a Broken Heart”, was previewed before the album’s release and was heavily focused on her relationship with her father. But what stood out even more was the music video, which Lindsay directed herself.
Not to make it about me, but this song and video were incredibly influential for me. It was the first time I saw a piece of media clearly reflect my own experiences—laid out in a way that felt accessible and digestible for a young audience. Confessions of a Broken Heart resonated deeply with teenagers who had strained relationships with their parents but maybe didn’t have the artistic or critical lens to find this kind of representation elsewhere. And that should count for something.
The album’s other notable track, “Edge of Seventeen”—a bold choice of a cover—drew sharp criticism. I suspect this, too, played a role in the album’s harsher reviews. Some probably saw it as egotistical, while others might have made the fatal mistake of comparing her to Stevie Nicks herself. But I don’t think Lindsay was trying to outshine the original—I think she was paying homage. She was trying to signal where she wanted to go next, artistically. But again, I’m a Lindsay apologist.
The Forgotten Single: Bossy
In 2008, Lindsay Lohan released her single “Bossy.” Written and produced by Ne-Yo, the song leaked online in early May before Universal Motown officially released it to media outlets. Despite being a catchy, club-ready track that marked a departure from her previous work, Bossy failed to gain traction commercially or critically. The song leaned into a more mature, sexier persona, following her role in I Know Who Killed Me (2007), where she played a stripper.
I truly believe Bossy never took off because of Lindsay’s standing in the media at the time. By 2008, her career was completely overshadowed by tabloid chaos. The previous year had been a public disaster: she was arrested for DUI and cocaine possession, spent a mere 84 minutes in jail due to overcrowding, and became Hollywood’s most unreliable actress. She had allegedly been dropped from The Edge of Love and was facing constant speculation about her career free-fall.
On top of that, rumors about Lindsay’s sexuality were swirling, and in 2008, she made her relationship with Samantha Ronson public. The media’s reaction was less about celebrating her queerness and more about framing it as another sign of her rebellious downfall.
Had Bossy been released under different circumstances—without the weight of scandal and relentless tabloid coverage—it might have been a different story. But by 2008, Lindsay Lohan wasn’t seen as a pop star, an actress, or even a celebrity to root for—she was just a walking headline.
The Pop Star Best Known as Lindsay Lohan
While Lindsay is most known for her acting career, I’d argue that her music was just as impactful—if not more so—for a certain generation.
The issue was never a lack of talent or vision but rather a rushed creative cycle, an overworked teenager turned young adult, and a general disdain for women in the 2000s. Lindsay’s music career was a reflection of who she wanted to be, but she was never truly given the time or space to explore that fully. I can see the slow roots of her carving out her artistic identity, but between relentless tabloid scrutiny, industry pressures, and personal struggles, she was always being pushed forward before she had the chance to figure it out for herself.
Had she been allowed to develop at her own pace, I truly believe she could have solidified herself as a legitimate artist. The vision was there—she just needed more time to bring it to life. For now, she remains a millennial touchstone, a symbol of both the era’s cultural highs and its most unforgiving pitfalls.
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