17. “California Sober” – Dancing With the Devil… The Art of Starting Over (2021)
It might be controversial to include such a song on this list, given that its title refers to a style of sobriety that Demi Lovato was testing out at the time that allowed her to drink and smoke marijuana in moderation—she has since rescinded these ways, and admitted that being completely sober is the only way to be. But the track represents so much more than just a faulty form of sobriety: it’s the pinnacle of her return to music following her highly publicized overdose, a method of forgiving herself and embracing the nuance in life.
“Tired of being known for my sickness,” she sings in its first verse. “It didn’t work, I’m trying something different.” Of course, it is difficult to look past lines like “cashing in my chips for forgiveness” in retrospect, but I think trying to find a way of being for herself during a turbulent time was something she needed to find forgiveness for herself. So she might be referring to finding freedom by letting herself casually drink alcohol and get high, but she’s also learning that nothing in life, including sobriety and recovery, is black and white. It’s all of the colors. And that lesson remains intact.
16. “I Hate You, Don’t Leave Me” – Demi (2013)
A bonus track from the deluxe edition of Demi that I’m pretty sure she has never performed live, “I Hate You, Don’t Leave Me”, is some of Demi Lovato’s most vulnerable music. It could be about a lover; it could be about her father; it could be about herself. It could be about you if you listen to the lyrics long and hard enough, which can be attributed to many of her ballads. “I’m addicted to the madness / I’m a daughter of the sadness,” she cries. It touches greatly on her abandonment issues and her need to feel loved, even at the expense of her well-being.
While Unbroken was considered her vulnerable, post-rehab album, she admitted in 2017 that she was not yet sober the first time after that first stint. She still drank heavily and abused cocaine during the recording and promotion of Unbroken, which can sometimes taint its overall message of easy breezy recovery. It’s moments like these on its follow-up Demi that convey the vulnerability that Lovato can channel into her songwriting. This talent can sometimes get lost when she’s busy trying to play a game of pop music charades.
15. “I Love Me” – Dancing With the Devil… The Art of Starting of Over (2020)
Released in March 2020 as the planned lead single from Demi Lovato’s “comeback” album, the record was ultimately delayed due to COVID-19. Lovato later changed course and only included the song as a bonus track, but after the heaviness and heartbreak of songs like “Sober” or “Anyone”, “I Love Me” was the perfect pop comeback single. “After all the times I went and fucked it up / I wonder when I love me is enough,” she posits over happy-go-lucky production.
It’s not hard to imagine why she bumped the song off the album’s standard track listing since it sounds like it could’ve been from a follow-up album to Confident, where she attempts to embrace her wholehearted self while still trying to meet feminine pop star ideals. I like to believe the isolation of the pandemic forced her to throw that goal in the garbage. Even so, “I Love Me” is still peppy, upbeat, and better than “Confident” at tuning out negative self-talk.
14. “Substance” – Holy Fvck (2022)
If “I Love Me” was Demi Lovato’s attempt at being herself while not stepping too far out of bounds, “Substance” flips the bird to every boundary ever imposed on her. A pop-punk and alternative rock single from the Holy Fvck record, “Substance”, reveals what the singer has been searching for all along. “Am I the only one looking for substance?” she asks. “Got high, it only left me lonely and loveless.”
While the song sometimes leans a little too far into the alternative rock avenue of “I’m not like all those mainstream sellouts,” it feels authentically Lovato and what she’s been wanting to shout at the top of her lungs for years. The music video shows the singer in a meeting with record executives as she promptly destroys the boardroom and jumps out the window, signifying that she’s more than ready to march to the beat of her drum. And we’re along for the ride.
13. “Anyone” – Dancing With the Devil… The Art of Starting of Over (2020)
Recorded just days before her 2018 overdose and planned to be part of a new album she was working on, Demi Lovato publicly debuted “Anyone” as a comeback performance at the 62nd Grammy Awards in 2020, one that generated a standing ovation. While incredibly depressing to listen to even on a good day, “Anyone” gets to the root of Lovato’s abandonment issues: having lost her management over her “choice” to break her sobriety, she felt that no one in her life was genuinely listening to her or what she needed. “I tried and tried and tried some more / Told secrets ’til my voice was sore,” she laments.
While it’s sad to think of a global pop star in such a lonely place where no one is hearing her, “Anyone” marks the end of one chapter of her career and the beginning of the next. The first stage was marked by telling secrets until her voice was sore and not ever getting to a place of inner peace. The next chapter encompasses being her honest self and learning to be okay with the fact that it might piss some people off. If it means something to you, let it cost you something.
12. “World of Chances” – Here We Go Again (2009)
Another thing the Here We Go Again album had going for it is that Demi Lovato worked with seasoned songwriters like Jon McLaughlin and John Mayer, the latter of which penned this overlooked track. Reminiscent of a mid-aughts Avril Lavigne ballad, “World of Chances”, is some of Lovato’s best work only because it’s another prime example of the versatility she’s capable of. The lyrics might not be anything overly personal, but where her peers might have been recording singles about how young people can change the world if only they try hard in school or something, Lovato was busy writing more mature songs with John Mayer. Of course, Lovato was still on Disney Channel, so we’re not talking about anything too mature. But for a teenage Disney star to showcase this much talent and promise so early in a recording career, “World of Chances” is wise beyond her years.
11. “Melon Cake” – Dancing With the Devil… The Art of Starting of Over (2021)
Demi Lovato has been public about how, as much as she has conquered drugs and alcohol repeatedly, a bone of contention remains her eating disorder, which she developed as a child. Extreme dieting to maintain feminine pop star ideals at the hands of her management during the first chapter of her career led her not to eat a real birthday cake for years. Instead, her management would present her with a melon cake, otherwise known as a watermelon, with whipped cream and a candle.
While “Melon Cake” is named after these struggles, it also deals with the prison of the mind when in the throes of an eating disorder. “Finally, get to do things my way,” she happily proclaims. You can find her starving for attention most days, but she won’t be starving for food. While countless Hollywood stars have suffered eating disorders in shame behind closed doors, this is another example of Lovato laying her healing and recovery bare for all to see in hopes that it will help herself and whoever needs to hear it. I’d love to hear the whole story about the person fired for chocolate in the backseat.
10. “Sober” – standalone single (2018)
While not as heartbreaking as its sibling “Anyone,” the release of “Sober” was harrowing on its own. “To the ones that never left me, we’ve been down this road before,” she sings, tired and worn out. But aside from the bravery it takes to fall off the wagon and then write and record a song about it for all the world, what’s always been most striking about “Sober” to me is her admission of loneliness. “Sometimes I just want to cave, and I don’t want to fight,” she declares. “Just hold me, I’m lonely.”
While loneliness is a fact of life, it can feel a hundred times worse for those struggling with addiction and mental illness. Learning to be okay on your own is one thing; being abandoned by those closest to you over it is another. Ultimately, there’s no happy ending or upside to listening to “Sober” alone. It’s someone who feels awful about themselves for screwing up when they have so many other people relying on them. It’s about feeling lonely and not having a clue of what to do to make yourself feel better other than indulge in your vices. But above all, “Sober” is raw, open, and honest.
9. “Skyscraper” – Unbroken (2011)
Before there was any number of heart-wrenching Demi Lovato ballads, there was “Skyscraper”. Released as her first single since entering rehab and later leaving Disney Channel, it was an apt response to all she had gone through until that time while equally empowering her young fanbase. There have been a lot of better ballads from the singer in the years since “Skyscraper” was first released, but none have as much significance in the singer’s discography. Indeed, this was her highest-peaking song on the Billboard Hot 100 for six years until “Sorry Not Sorry” overtook it in 2017.
“Skyscraper” also established Lovato as much more than the pop-rock songstress whose music videos were consumed by youngsters during commercial breaks on Sonny With a Chance. “Skyscraper” was our introduction to Demi Lovato, the woman, and the fact that she struggled greatly during the Unbroken era signifies how much more human she is.