Lindsay Lohan's Musical Career: What Went Wrong?

by Aleksander Chan and Kelsey McKinney

Lindsay Lohan’s debut album, “Speak,” will be ten years old this year. What a world! But with the debut of her OWN docu-series, “Lindsay,” what better time is there to consider Lohan’s long-abandoned music career?


Kelsey McKinney: This track, from Freaky Friday, is Lindsay’s first big blockbuster hit, but all I remember about it is that Jamie Lee Curtis takes her door off and then my father threatened to do that to me for YEARS.

Aleksander Chan: I remember this movie teaching me that the House of Blues is a thing and that if you get really pissed at your mother and you both wish on a fortune cookie or something then you will swap bodies.

Kelsey: Is that what happened? I’m pretty sure this movie was actually about Lindsay Lohan pretending to be Jamie Lee Curtis pretending to not like kissing some boy with floppy hair.


Kelsey: Chad Michael Murray! Everyone’s preteen love.

Aleksander: Anyway, “Ultimate” is the song Lindsay sings (“sings?”) as part of the plot at the end.

Kelsey: Yeah. And I’m pretty sure she’s actually singing. It might have been the first song she sang for mass audiences. Especially since Freaky Friday is one of the only Lindsay movies that made big $$$.

Aleksander: It’s a pretty safe introductory song. You can hear her voice layered through at least two others. It’s poppy. Right on trend for the time (2003), where eff-you girls like Avril were tellin’ it on the radio.

Kelsey: Yeah, but it’s much more positive than that. I mean “Crazy in Love” came out that year. This is kind of the 14-year-old version of that. In terms of subject and voice, Lindsay Lohan is NO Beyoncé. There’s also a very Avril-esque guitar background. Her voice sounds scruffy, kind of like it does now after all those cigs.

Aleksander: Oh yes, you can definitely feel the Disney sheen. Those calculated guitars. Its just-left-of-empowering theme (“you’re the ultimate you!” teehee).

Kelsey: “No lie!”

Kelsey: But this did kind of break her out of her one-trick-pony acting shell.

Aleksander: Yes, as in, “Lindsay can competently act but also sing vaguely on key.”

Kelsey: Exactly. But that’s huge for a child star.

“Drama Queen (That Girl)”

Kelsey: Before Freaky Friday, Lindsay’s only claim to fame had been her role as those twins in Parent Trap and being a Disney Channel Child. The ability to sing gave her the option to become the singing/dancing/acting triple threat. I mean, “Teenage Drama Queen (That Girl),” from Confessions of a Teenage Drama Queen, is an empowering ballad about a girl who “always believed that she was gonna liver her dreams…” Which for Lindsay, must have included singing because she does an awful lot of it in this movie.

Aleksander: It’s basically a whole movie about Lindsay thinking, yearning, and talking about singing. And then she does. Over. And over. And over. THAT GIRL WAS A ONE TIME TEENAGE DRAMA QUEEEEEENNN.

Kelsey: She also dances, kind of? I mean. If you count that weird skipping thing as dancing.

Aleksander: I mean she “dances” about as well as wannabe hip white girls do, ya know?

Kelsey: Definitely. That’s fair. But it really does seem like in this movie, Lindsay is trying to set herself up for a music career, no?

Aleksander: Definitely. Maybe that’s why, as a movie, it’s kind of garbage: It’s a thinly-veiled video cover letter for all the things Lindsay Lohan can do for YOU, casting agents and movie studios that are not Disney.

Kelsey: It could have been a manipulative move for her too. 2004 was a YEAR OF LOHAN. In one year, she had this weird singing thing, Mean Girls, and RUMORS.

Aleksander: Oh, true. And, like, sonically, the song is a catchy little number. Definitely has a hook. You can tell her voice has developed since “Ultimate”/Freaky Friday.

Kelsey: Yes. It’s not as incessantly repetitive as “Ultimate,” and also features something that’s pretty common in most of LiLo’s musical canon: FUTURE PREDICTIONS OF HER LIFE.

Aleksander: YES. DID SHE KNOW? Because we know now.

Kelsey: Right. When she says things like “A hot, tough everyday wannabe.. .but she’ll have changed her destiny… now she’s a somebody.” Did she know she was about to be a somebody? That she was the “wild child dreamer”?

Aleksander: And the chorus is like her telescoping out her own future: “that girl was a ONE-TIME teenage drama queen.” It’s as if her star was already beginning to fade.

Kelsey: Yes. Like with real stars. You can’t know they’ve died (exploded?) until years later.


Aleksander: Speaking of prescience. “Rumors,” the first single from Lindsay’s first studio album, which was released in December of 2004, is UNCANNY.

Kelsey: This song could really be the anthem to the last 10 years of Lohan’s life.

Aleksander: God, if she thought she was dogged by paparazzi and gossip THEN, imagine how she feels now.

Kelsey: I mean, to her credit she did “do it her way” as she sings.

Aleksander: YEAH SHE DID.

Kelsey: Sometimes “our way” just isn’t the best way though.

Aleksander: Her first album, “Speak,” reminds me a lot of later-years Britney, in that voice-as-additional-effect sense, like her voice is just another noise to add into a mix here.

Kelsey: Yes, like post-”Circus” era Britney, when her voice was gone and all it really did was provide the melody for the electronic symphony behind her. It’s also maybe a symptom of Lindsay’s limited vocal range.

Aleksander: Yes, you’re the one with perfect pitch. So… she can’t really sing, right?

Kelsey: Lohan, like many child film stars turned musicians, can sing in the sense that her voice on the CD is (mostly) on key. She cannot sing at all in terms of talent. She has maybe two octaves and they were probably both trained by a professional. Anyone with a voice coach could get where she was unless they were totally tone deaf.

Aleksander: So like Ashlee Simpson.

Kelsey: Yeah. Exactly like Ashlee Simpson.

Aleksander: Which is a good analogy, because both of their debut albums were about, broadly: boys, disillusionment about fame, how being disillusioned about fame makes boys not like you.

Kelsey: And both of their first CDs set them up to have a decent music career.. Ashlee Simpson’s demise was that she got caught lip-synching before anyone else. Lindsey’s was a little more complicated.


Aleksander: I actually like this song. She kinda-sorta sings on it. And is also prescient!

Kelsey: It’s both prescient and ~relevant~! Lohan writes about a relationship ending and while this is probably meant to be about her and some boy person, this is the year before her father is sentenced to prison and her parents separate again. Really, this could totally be a song about her father.

Aleksander: YES. I see it. But what I also hear when I listen to this song is a grim acceptance of the looming downward spiral of her career. Let’s go to the lyrics:

I watch the walls around me crumble / but it’s not like I won’t build them up again
Here’s your last chance for redemption / so take it while it last cause it will end

Honestly, tell me that it’s over
Because if he world is spinning, and I’m still living

And I’ll be the first to go / don’t want to be the last to know

Kelsey: YES. This is a kind of early eulogy to a career that hadn’t even begun to crumble at this point. In 2004, she was at what was probably the HEIGHT of her fame. Everyone knew her. She had two hit movies (one of which became a cult classic) and this semi-catchy CD in one year.

“Jingle Bell Rock”

Kelsey: Speaking of cult classics. Does she even sing in Mean Girls? I can’t remember.

Aleksander: Oooo, maybe not, but it doesn’t matter? Because this, from the movie, is arguably the most prominent “musical” moment of Lindsay’s career, which is sad given how she released two albums. Like, more people know that 90 seconds than her entire “music career.”

Kelsey: This is definitely the shiny moment of what was a lot of effort for her. We’re talking “Jingle Bell Rock” here, right?

Aleksander: Right. Wow though, maybe that’s just residual shine from Mean Girls, which ALSO TURNS 10 this year.

Kelsey: I mean, she does save the day with her voice right? This is just more evidence that she WANTED this music career. In fact, she had a five CD contract with a producer. She had plans to make ~moves~

Aleksander: God. This is disappointing to learn given how much I like her second album.

“A Little More Personal (Raw)”

Kelsey: This title is, IDK, apt. She moves on from the general “I’m famous and like boys” into some real shit in this second CD, released at the end of 2005. I’m not sure I would call it raw, but it is certainly “a little more personal.”

Aleksander: Yes, it’s definitely more revealing than anything else she’s ever recorded. Acted in even.

Kelsey: If you look at the canon of her movies, she had very little control over her role or the plot of the movie. All of that was decided ahead of time for her and while she could make some minimal changes, she didn’t have a lot of artistic control. The same goes for her first album. But on A Little More Personal (Raw) we see Lindsay bring out her own artistic control a little bit.

Aleksander: For sure. And even in the album credits, the number of writers and producers have been seriously pared down here. It’s mostly go-to scorched earth songstress Kara DioGuardi, who, natch, wrote some songs for Ashlee, Kelly, P!nk, and the like.

Kelsey: And when you break the album down into the songs she actually worked on (read: *cowrote*) it’s really interesting how many of those songs delve into Lohan’s personal life. She is really self-reflective in some of these.

“Confessions of a Broken Heart (Father to Daughter)”

Aleksander: Speaking of, THIS song. THIS FUCKING SONG. And the video. They are a TEXT. So much is happening. So much is revealed. So much is felt.

Kelsey: YES! Can we talk about this song? And also the VIDEO.

Aleksander: It’s like, WHERE DO YOU EVEN START???? From the top:

I wait for the postman to bring me a letter
I wait for the good Lord to make me feel better
And I carry the weight of the world on my shoulders
A family in crisis that only grows older

Her father has just been sent to prison for the SECOND time, for assault and a DUI (previously: insider trading). Lindsay, blighted but not quite troubled (yet) teen actress/singer is left to be her family’s sole breadwinner. What a fucked position to be placed in at 19-years-old.

Kelsey: YES. Additionally there’s this weird juxtaposition of all of her family drama and her professional career. Here’s a song full of angst and hardship. Her parents who have had a rough relationship for almost her entire life are officially separating. Her father is in prison. Her mother is a failed dancer, and in one fell swoop Lindsay, at 19, becomes the only positive member of her family. She has three younger siblings, one of whom plays a pretty large role in the music video for this song, that she’s supporting. AND in another weird twist of timing, Herbie: Fully Loaded comes out this year in which she plays second fiddle to a very happy animated car. Talk about emotional variance.

Aleksander: For real. And to me, this song might be the first (maybe only) genuine moment we’ve seen from Lindsay. Even in her better acting roles, I’ve only ever found her to be perfectly competent. There’s a reason why Rachel McAdams and Lizzy Caplan and Amanda Seyfried and Tina Fey and basically every other actor in Mean Girls out-acted her — on-screen she’s never seemed completely willing to let herself be someone else. To look silly or seem truly serious. She’s always Lindsay Lohan Acting. But music, right, is different, at least as a type of performance, and especially at the age she was. The reason why “Glee” worked so well (at first) was that it understood that, for young people, sometimes music is best and only way to express themselves, because there’s an inherent sense of drama to music that’s easier to channel feelings you can’t quite understand. Sometimes, the only way to get it out (to get ANYTHING out) is to sing it, and I feel like that’s what Lindsay did here, and like so many of us did in those late teen years, stumbled upon profundity.

Kelsey: But even in the music video here she’s “acting” right? And it seems more genuine than any other role she’s ever performed. In a prom dress sitting on the floor of a blue cast bathroom she actually looks miserable. She looks like this is a role she’s played before in real life, not on the screen. Which she certainly has. Her father’s behavior in her family is certainly worth writing this song over. This song, when you really look at the lyrics is incredibly depressing. It’s rough, emotionally. I mean, she straight out says “Tell me the truth, did you ever love me?” What could be more depressing? Which I think really tells us a couple of things: Either Lohan is an incredible actress, but only when the role requires real severity and seriousness, or she’s drawing off her own past experience and music is the only real way for her to get there.

She co-wrote this song. Now that could just mean that she sat in the meeting where they made up the lyrics, but I think this is the only time we see real emotion from Lindsay. And she’s at the perfect point in her career to do it. At this point, the worst thing that has happened to her is a couple of car accidents because of paparazzi (a la “Rumors”), and a few negative reviews. In 2005 when this song came out, Hollywood was hers to take.

Aleksander: Mmmmmm, yes, good. That line, “Did you ever love me?” wrecks me every time. What a devastating idea for a child to ever have to consider about their parent. That’s probably the most revealing “confession” she makes. And it doesn’t feel like teenage melodrama (though certainly plenty of other tracks on A Little Personal [RAW] are) trumped up with high emotional wattage — she’s worried that her father might never have actually loved her. Which, oof. But the VIDEO.

Kelsey: YES. the video is even WORSE.

Aleksander: She directed the video herself, which adds a certain layer of vérité sophistication to it. And she’s very forthcoming here, outright painting her father as abusive to her mother (in more ways than one). The staging — her life, her family’s coming undone — is literal theater to the masses. Yes, it is overwrought and little too on the nose, but teens are good at not stultifying their emotions, so it works for me. It feels oddly pure. Though, lol, Linds, dressing yourself like that to cry in the bathroom. Just because you’re having a breakdown doesn’t mean you have to give up your vanity I guess!

Kelsey: Ditto to the wardrobe. And I think this literal theater is even more amplified by the fact that the little girl dressed in the ballet outfit who is presumed to play her in the video is actually Ali Lohan — her little sister. She obviously would have experienced the same kind of abuse and her presence in this video is a real amplification by Lindsay of just how deep this heartbreak runs. Ali went on to her own weird kind of fame when she starred in the short-run Lohan family reality show, but in this video she, too, has no problem channeling this overwhelming (if overwrought) emotion, which leads me to believe that neither of them are really acting at all.

Aleksander: To me, this video reads as a cry for help — for Lindsay, Ali, the entire Lohan family. Her life is falling apart in front of us and we look upon all of it as pure spectacle, as outside and beyond ourselves. I’m not trying to absolve Lindsay of any and all responsibility, but I wonder what kind of Lindsay Lohan we would have now if someone like Oprah had stepped in at this point and just said, “Hey, you need some help?”

Kelsey: EXACTLY. And retrospectively, its really easy to recognize her role in the production of this entire album as just that: an open cry for help. The Lohan we know who is in and out of rehab with a smoking problem and no ability to hold down a good acting job, did not exist when this song/video was released. The public couldn’t jump on this as fact just as we can’t jump on any country song about cheating. Sure, in retrospect we know that she felt a ton of pressure and was living out of a hotel most of the time while sending money back across the country to her family in Long Island. But at the time all the public knew was that her father was going to prison, and she had just released this CD. Compared to “Speak,” “A Little More Personal (RAW)” was a total flop. Speak went platinum pretty quickly and peaked at number four, but the highest her second album reached was 20. This album wasn’t really that popular. It didn’t have a number one single, and songs like this one weren’t catchy enough to become number one singles. We missed this album the way we missed the obvious struggle she was experiencing.


Aleksander: AKA, that weird one-off dance-y 2008 single from an unfinished album that kind of went nowhere.

Kelsey: Yes. I completely missed this song in my Lohan education. It wasn’t until someone mashed up this song with Ne-Yo (who wrote the song) earlier this week that I heard the only released song from what I think we can refer to as “the lost album.”

Aleksander: OMG that Ne-Yo remix is GREAT. A+ job on that, internet. But given the chronology of this song, it’s a wholly disappointing experience, no? Especially to go from the improvement of her second album to this Britney B-side. Though it does broach the whole “women be bossy” topic!

Kelsey: YES! I mean, this too seems kind of prescient with the recent Sheryl Sandberg/Beyoncé/others “ban bossy” campaign but it’s really just kind of a coincidence like the fact that Lohan has a song called “can’t stop/won’t stop” or that she sings “you only live once.” Ultimately, “Bossy” — regardless of the remix — is kind of the nail in her musical coffin. With “Confessions of a Broken Heart,” Lohan was at least giving us some heart. She was trying something. But here, with “Bossy” it feels like a Ciara club-remix gone wrong. There’s nothing to this song, and honestly, I can’t imagine Lohan being “just a little bossy.” She seems a LOT BOSSY. But whatever. This is the end of her career, for now. After this she goes to rehab. She goes to jail. She gets plastic surgery. She falls into all of the traps her father fell into before her. It’s actually really sad.

Aleksander: 🙁 It’s her last song before living down to the expectations she probably had for her father. 🙁 🙁


Aleksander: So the thing is, I do not care to ever see Lindsay act in a movie again, unless it is funny and she does seem wooden in it, which based on her new docu-series just seems impossible at this point. BUT. But. I would actually root for a musical comeback! Because I wasn’t lying when I said I actually liked her second album. “If It’s Alright” is more than all right in my book. I put it on my phone. It’s good elliptical music.

Kelsey: I completely agree, but have the opposite feeling about the movies. If Lohan could score a role with a director who could keep her in line and funnel some of that “Confessions of a Broken Heart” rage into a character, you know what, I would pay the $14 and buy the popcorn and watch it. I would probably even not hate it. But if Lohan announced a new CD, I would stream the shit out of it. No amount of crazy can keep a good CD from being made. I mean, look at Britney’s Circus or whatever Lady Gaga is doing. Rehab is a CAKE WALK for musicians, and I’d love to hear more Lindsay music. It grew on me. As long as she promises to never ever ever do a cover again. Ever.


Kelsey: For the love of your female god, Lindsay.

Aleksander: But yes, L I N D S AY, sing again. We’re listening.

Aleksander Chan is a writer and editor. He’s moving to New York like right now. Kelsey McKinney is a writing fellow at Vox. She’s moving to D.C. in May.