Lindsay Lohan Never Got Enough Respect as a Musician

Lohan’s career in music is all but forgotten — but in the early aughts, she was the problematic punk princess of pop. Is the ‘Mean Girls’ star primed for a comeback?

On Friday, Lindsay Lohan released her first single in 12 years. It’s called “Back to Me,” and it’s a generic EDM-pop number that could’ve been pieced together from Kygo’s cutting room floor. Lohan sings about her alcoholism and troubled family. “I know I drink too much, but it’s okay,” she proclaims. Girl, are you sure about that?

If you didn’t know, Lohan is a successful musician — yes, musician — with several charting singles. She released two full-length albums as pop’s most problematic punk princess in the early aughts before her legal troubles derailed her career.

The ’90s child actress turned ’00s tabloid celebrity has spent over a decade attempting unsuccessful re-admittance into Hollywood’s good graces. She tried an insufferable indie film with a male porn star in The Canyons; she performed in a lukewarm production of Speed-the-Plow on London’s West End; there was a dramaless reality TV show called Lindsay Lohan’s Beach Club. Even Oprah gave up on Lindsay.

But music is the one area of Lohan’s surprisingly multifaceted career where she’s found reliable success. As the aughts revival inches closer, is Lindsay primed for an inevitable comeback?

Stage 1: Disney’s Family-Friendly Avril Lavigne

In 2003, Lohan was another child star working the Disney Channel circuit, having starred in The Parent Trap, Life-Size and Get a Clue. Alongside Hilary Duff and her then-roommate Raven-Symoné, Lohan helped relaunch Disney’s struggling label Hollywood Records.

Her debut single, “Ultimate,” a guitar-heavy pop-punk number, appeared on the soundtrack for Freaky Friday. For the 2003 body-swap film alongside Jamie Lee Curtis, Lohan learned how to play guitar and sing as a moody teenager who plays in a garage band called Pink Slip. While “Ultimate” never found commercial success, Disney Radio played the record endlessly and established Lohan as a family-friendly Avril Lavigne.

In 2004, Lohan followed up with a series of standard covers on the Confessions of a Teenage Drama Queen soundtrack, including Stevie Wonder’s “Living for the City” and David Bowie’s “Changes.” But the real standout track was the ’80s synth-pop rock single “Drama Queen (That Girl).” Finally, 2000s girls and effeminate boys like me — likely influenced by our older siblings’ Third Eye Blind and blink-182 obsessions — had glittery pop-rock anthems to sing into our hairbrushes at night.

Lohan’s traditional trajectory from Disney princess to Hollywood star was fastlined later that year when Mean Girls became a critical hit and cult classic. She signed with producer Tommy Mottola, who’d launched the careers of ex-wife Mariah Carey and Jennifer Lopez. Lohan re-signed with Mottola’s Casablanca Records for “Back to Me.”

At this time, her It Girl image solidified. She got in a bitter feud with Hilary Duff over Aaron Carter and developed a tabloid reputation as a party girl. According to a (deeply 2000s) Rolling Stone profile, Lohan’s 18th-birthday invite list included Tara Reid and Nicky Hilton.

At the end of 2004, Lohan released her debut album, Speak, borrowing sounds from Janet Jackson, Britney Spears, Avril Lavigne and Destiny’s Child to create a discombobulated string of empowerment platitudes. The best thing you could say about the album is that it reflected… teenage frenzy?

Still, Speak produced her best song to date. “Rumors” is an infectious dance-pop track, all about squashing tabloid rumors and embracing her growing party-girl persona. “I’m tired of rumors starting / I’m sick of being followed / I’m sick of people lying / Saying what they want about me / Why can’t they back up off me? / Why can’t they let me live? / I want to do it my way / Take this for what it is,” Lohan sings in the chorus. The song was certified Gold with the Recording Industry Association of America.

Fifteen years later, “Rumors” no longer sounds like female independence. It’s a painful warning sign of the messy downward spiral to come. The texture of Lohan’s wavering vocals read as a cry for help packaged as a moneymaking defiance-anthem single. But the song is undeniably infectious: It’s got a dance-worthy beat and juicy behind-the-music gossip. It’s pure ’00s nostalgia bait.

The rest of the Speak album is a solid string of serviceable tracks optimizing the era of Von Dutch hats, Marc Ecko sneakers, puka shell necklaces and side bangs. “First” is rumored to be about Wilmer Valderrama breaking up with her to date Ashlee Simpson; Simpson responded with her own single, “Boyfriend,” off I Am Me, recreating Lohan’s “First” music video. Alongside “Over” and “Speak,” Lohan developed a knack for turning her melodramatic personal life into pop bangers.

 

Stage 2: Daddy Issues

Almost exactly a year later, when the partying had eclipsed her acting career, Lohan released her sophomore and most recent album A Little More Personal (Raw). The two albums are polar opposites.

For the Speak cover, a naturally auburn-haired Lohan is seen in a senior-year portrait surrounded by notebook doodles and yearbook scribblings. Speak presents a moody teenager set to make her own way in the world. The A Little More Personal (Raw) cover is the profile of a blonde woman, revealing her arched, tattooed lower back. Badass.

But just like on her debut album, Lohan dove into her increasingly tumultuous personal life. Her deeply troubled parents, Michael and Dina, gave her ample material; so did the rotation of boyfriends and starlet frenemies.

“Confessions of a Broken Heart (Daughter to Father)” is a piano ballad, a letter to her father who first went to jail when Lohan was 11 years old and had just been charged with a DUI. It’s a shame the tragic, gossipy tales throughout the album outshine Lohan’s surprisingly powerful raspy vocal register.

Stage 3: EDM Boss

The following years saw Lohan fully tip the scale from Hollywood potential to problem. There were car wrecks, a rumored sex list, endless legal troubles and stints in rehab. She grew skinnier and blonder. Her music career was sidelined and eventually forgotten.

For over a decade since her pop-star heyday, Lohan has tried repeated attempts at a musical comeback, including just six months ago with “Xanax” (released only on Instagram).

The best attempt came in 2008 with “Bossy,” the campy second installment of an immaculate series of starlet dance-pop anthems to narcissism. The bookends are Paris Hilton’s deeply underrated single “Stars Are Blind” and Schitt’s Creek star Annie Murphy’s perfect spoof, “A Little Bit Alexis.”

“Bossy” was another promising start for what could be a good foray into an EDM career. But no album materialized. That’s Lohan’s career in a nutshell: flash-in-the-pan success unable to be nurtured by an erratic star.

Stage 4: A ’20s Comeback?

Given Mean Girls’ endlessly quotable lines and constant rotation on cable TV, we’re still constantly reminded of how captivating Lohan was at her best. However naive as it may seem, I’m still convinced she can make a comeback.

She was the most talented of her lot, all of whom have sobered up and made a comeback. Paris Hilton became a respected DJ; Nicole Richie is a fashion mogul and actress with a new Quibi comedy series; Britney Spears is a socialist pop star once more. Lohan is still the only girl at the club. But “Back to Me” doesn’t make it seem like she’s ready to leave.