Long before Lindsay Lohan became the Greece-traversing, memeable dance-loving, beach club businesswoman, she was the ultimate teen queen — not only ruling the box office with films like Freaky Friday and Mean Girls, but also taking on the pop world.
After establishing herself as a movie star, Lohan became one of the frontrunners of the era’s pop/rock boom thanks to 2004’s Speak. The debut album boasted singles like “Rumors” and “Over,” which led to its No. 4 peak on the Billboard 200 chart. Lohan quickly followed up with sophomore LP A Little More Personal (Raw) in 2005. Peaking at No. 20, it was led by the vulnerable “Confessions of a Broken Heart (Daughter to Father).”
Now, the 33-year-old has finally returned to music with “Back To Me” — her first official single in 12 years. The dancefloor anthem finds her reflecting on her troubled past and learning how to move on, which is all set to a catchy house beat. In celebration of Lohan’s comeback, Billboard has gathered 10 of the star’s most essential songs to date.
10. “Back To Me” (2020 single)
Lohan has had her fair share of ups and downs, but she’s ready to free herself from that darkness on this party-ready jam. “My life is full of ripped up pages / I’ve been weak, contagious / But I’m coming back, I’m coming back to me,” she muses atop a floating, synth-based melody. The combination of self-aware lyricism and thumping dance production is worthy of an addition to the “Crying In The Club Anthems” Hall of Fame. — BIANCA GRACIE
9. “Magnet” (Speak, 2004)
Leave it to Lohan to make science sound so cool. “Magnet,” a fan favorite deep cut on Speak, is the singer at her most lovestruck as she tries to pull herself away from her crush. But of course, just like a magnet, she simply can’t get away! “Is it gravity, chemistry, physically pullin’ me? / What could it be, boy?” she ponders as the song’s guitar riffs come crashing down. — B.G.
8. “Edge of Seventeen” A Little More Personal (Raw), 2005]
It’s almost sacrilegious to think of touching a Steve Nicks classic, but the fearless Lohan took on the challenge of covering 1982’s “Edge of Seventeen.” Found on A Little More Personal (Raw), Lohan’s rendition is revved up for a more modern generation, complementing that iconic bass line with thrashing hard rock riffs and breathy coos. The singer later performed her cover at the 2005 AMAs, channeling her inner late-‘70s rock goddess. — B.G.
7. “First” (Herbie: Fully Loaded OST, 2005)
How do you get a guy to make you his priority? Write a kickass pop-rock song, at least according to Lohan. “First” is an in-your-face declaration of what a girl wants, with forward lyrics (“I used to be a girl who could let a guy breathe/ But you’re mine/ And tonight you revolve around me,” Lohan sings in the second pre-chorus) and a gravelly, undulating guitar riff. Whether or not the feisty proclamation successfully lands a guy, the amped-up energy of “First” at least gives you the confidence that it will. — TAYLOR WEATHERBY
6. “Confessions of a Broken Heart (Daughter to Father)” A Little More Personal (Raw), 2005]
As the title of her sophomore album stated, Lohan aimed to get a little more personal and reveal the darkest corners of her life. “Confessions of a Broken Heart (Daughter to Father),” the album’s sole single, served as an open letter to her estranged father Michael Lohan. Co-written by Lohan and Kara DioGuardi, the emotions throughout “Confessions” are near-tangible as the singer tries to cope with her father’s incarceration and their failed relationship. Those lamentations carried the song to No. 57 on the Hot 100. — B.G.
5. “Ultimate” (Freaky Friday OST, 2003)
Any teenage girl in the early 2000s who had dreams of being in a rock group lived out those aspirations Lohan’s character in 2003’s Freaky Friday. The film closes with her band rocking out on a song called “Ultimate,” a spirited (and adorably innocent) anthem to a guy who went from a reliable friend to the “ultimate” boyfriend. The tune’s raw guitars give the lovestruck sentiment a little edge, making anyone want to find a badass who can shred like Lohan. — T.W.
4. “Over” (Speak, 2004)
Breakup songs can hit you where it hurts, and Lohan’s “Over” is no exception. But instead of making you curl up in a ball and sob, “Over” provides catharsis in the form of a belt-along. Sure, the lyrics are extremely pained (“‘Cause if the world is spinning and I’m still living/ It won’t be right if we’re not in it together,” Lohan wails in the chorus), but the dynamic chorus of “Over” feels so good to scream that you almost forget you’re singing because you’re sad. Now that’s how you get over heartbreak. — T.W.
3. “Bossy” (2008)
Lohan teamed up with hitmakers Ne-Yo and Stargate for this supremely catchy bop that would still get the dance floor jumping 12 years after its 2008 release. The singer’s signature throaty vocals were perfectly suitable for the tune’s amped-up sass factor, as she insisted on taking charge. “Trust me / You want me happy / Punishment can be severe,” she warned on the bridge.
“Bossy” was meant to anchor Lohan’s third album Spirit in the Dark, but unfortunately it was left unreleased. Nevertheless, the track managed to score modest fan love as it topped Billboard’s Dance Club Songs chart. — B.G.
2. “Drama Queen (That Girl)” (Confessions of a Teenage Drama Queen OST, 2004)
Confessions of a Teenage Drama Queen may not have been Lohan’s most iconic film, but it spawned arguably the most classic pop song in Lohan’s catalog: “Drama Queen (That Girl).” Between the punchy beat, racing melody and empowering lyrics, “Drama Queen” is pop perfection — and even features a little rap on the bridge to take Lohan’s prowess to a new level. If there are doubters and non-believers, one of these days they will re-listen and know that they were wrong. — T.W.
1. “Rumors” (from 2004’s Speak)
The song that started it all. “Rumors” was not only Lohan’s debut single, but it also served as her official entrance into the pop world as she aimed to compete with the likes of Ashlee Simpson, Britney Spears and her then-rival Hilary Duff. She teamed with the Grammy-winning Cory Rooney (Mary J. Blige, Mariah Carey, Jennifer Lopez), as well as Tito Jackson’s sons Taryll Jackson and T.J., for what essentially was a middle finger to those who contributed to her career’s backlash.
At the time, Lohan was caught in a media frenzy as the paparazzi tracked down her every move. She channeled that frustration into “Rumors,” which fuses sharp synths and R&B-inspired melodies for a feisty party tune. Who knew the defiant lyric, “I’m gonna do it my way / Take this for just what it is,” would ultimately turn into Lohan’s mantra for years to come? — B.G.
