8. “Warrior” – Demi (2013)
Simply put: without “Skyscraper”, there would have been no “Warrior”. While never released as a single, the song took on a life of its own thanks to its easily relatable refrains of barring a secret to the world that has never been shared. “I’ve gotta get this off my chest and let it go,” Lovato proclaims in the song’s opening lines. “All the pain and the truth / I wear like a battle wound.” Years later, she would disclose on Twitter that “Warrior” was about childhood sexual abuse, something that’s perhaps easier to recognize when listening with adult ears: “There’s a part of me I can’t get back / A little girl grew up too fast / All it took was once, I’ll never be the same.”
What makes “Warrior” all the more empowering is comparing it to how, just two albums earlier, the singer was discouraged from including songs with heavier, more mature meanings for fear of alienating her younger audience. But it was precisely that more serious, more mature subject matter that bonded Lovato with her fanbase in ways that her first two albums did not. Many young people listening to her music have gone through equally distressing struggles, and hearing a public figure like Lovato put those experiences into words helped contribute to her legacy as we know it today.
7. “29” – Holy Fvck (2022)
As part of reclaiming the anger that Demi Lovato had choked down for so long on Holy Fvck, “29” shocked and delighted audiences when it was released as the third single from the record last August. Its lyrics refer to a long-term relationship the singer had with an older man, which began when she was 17 and he was 29. Longtime fans need not hesitate for a moment to know which long-term man Lovato was most likely referring to. It was all the more jarring since her management had perpetuated a narrative that the singer and the man remained close friends despite their separation.
Whatever the case, Lovato clearly expresses her displeasure and vitriol at how she was manipulated by a man much older than she was, referring to herself as “just five years a bleeder” and how at the time, it felt like a teenage dream fantasy. But the reality was quite different. Like how she built bonds with her fanbase over shared scars during her younger years, women sharing similar experiences with older men on social media in response to “29” was quite impactful.
6. “Give Your Heart a Break” – Unbroken (2011)
Arguably Demi Lovato’s most overplayed single on mainstream pop radio got that way for a reason: “Give Your Heart a Break” is pretty much perfect. While perhaps more generic or impersonal than other offerings on Unbroken, the song displayed Lovato’s affinity for pop music in a way that satisfied boundaries while also musically toying with different hats she was able to try on. “Give Your Heart a Break” is debatably more mature than most of the Demi album, an LP the singer described as more her speed than the sounds she experimented with on Unbroken.
But Lovato’s third studio album managed to satisfy her existing Disney audience while establishing her as an adult pop singer. “Give Your Heart a Break” sounds like it could have been sung by any number of older, more established female pop singers at that time, but no one would have done it as well as Lovato.
5. “Fix a Heart” – Unbroken (2011)
Another quality of Unbroken was that it toed the line between jovial and self-reflective in a cohesive manner compared to Demi, which felt younger melodically. “Fix a Heart” combines Lovato’s newfound autobiographical nature with the foundation of a good love song: one that rips off the bandage to look at the harsh truths beneath. As Demi Lovato sings, she just ran out of band-aids, and even though we can bandage the damage, you never really can fix a heart. It’s a cliché with some truth to it.
While we can do all of the emotional homework in our power to heal ourselves, there will always be a part of ourselves—our heart—that contains scars from whatever wreckage it needed to recover from in the first place. “Fix a Heart” is also personal in the best way, in that most of its lyrics suggest you never really can fix a heart, until the last line when she laments, “You never really can fix my heart.” It’s a method of exposing herself in a way that generates respect.
4. “Happy Ending” – Holy Fvck (2022)
Until Demi Lovato came out as non-binary in 2021, it was easy for the fact that she was already queer to slip under the radar. After all, she had dedicated herself to fulfilling the role of a feminine pop superstar for several album cycles, an image that doesn’t necessarily leave room for or cater to the incorporation of queerness. That was another liberating aspect of Holy Fvck: it felt like Lovato was finally just to be herself, whoever that might be at the moment. As a queer person, she can pick and choose elements of her identity as she goes, something that scares most heterosexuals into hate speech.
This is why “Happy Ending” is one of the strongest songs in her catalogue. Its opening lines refer to her meeting God just for a minute, sitting in his house, and finding she didn’t fit in. But she goes on to realize that she might not fit in anywhere: she’s tried every road of healing and recovery, and she’s tried to be our hero by lending us her voice, but it still doesn’t fill the void. “Am I gonna die trying to find my happy ending?” she asks. Not only is it an intense reflection for Lovato, but it also manifests many of the inner demons queer people shove down daily.
3. “Tell Me You Love Me” – Tell Me You Love Me (2017)
If it wasn’t already made clear, some of Demi Lovato’s best work has come out of her experimentation with R&B, so I’m still inclined to pick her sixth studio record, Tell Me You Love Me, as her magnum opus. At the time, the singer had been reeling from the end of a six-year relationship that may or may not have been the subject of “29”. As a result, much of the album’s lyrics grapple with her learning how to be single and be by herself, which encompasses the fun and laughter of a night out or a casual hookup to the depressive lows of learning to be alone.
“Tell Me You Love Me” falls somewhere between these two extremes. It acknowledges Lovato’s tendency to get too close too fast due to not knowing how to be on her own and her lifelong emotional issues that have primarily defined most of her adult work. As such, the song feels definitive for the singer, even if her narrative was about to flip upside down about a dozen times in the years that followed the Tell Me You Love Me album.
2. “Don’t Forget” – Don’t Forget (2008)
The only song on this list from Demi Lovato’s debut studio album that still rings true as a masterpiece 15 years later. The kind of creation leaves its listener greatly impressed that it was written and performed by a 16-year-old. If the singer hadn’t been a Disney Channel star then, I imagine it could’ve received a reception similar to that of Olivia Rodrigo‘s “Drivers License”. When Lovato returned to her pop-rock roots for Holy Fvck, she commented that she knew she could “go this hard” during her initial Disney days, but she didn’t feel she could accomplish it as well as she can now as an adult. Whether or not that’s true remains to be seen. The singer took a mold warmed up for her by the Disney pop rock of Hilary Duff and said, “I’m in it for the long haul.”
1. “Stone Cold” – Confident (2015)
Demi Lovato’s best performance all around ironically hails from one of her weakest LPs, but we’re going to overlook that for argument’s sake. No matter how many times I’ve heard it, I cannot listen to “Stone Cold” without getting full-body chills. A timeless ballad about the one that got away, the singer is lovelorn about how much it hurts trying to be happy for someone who could have been someone significant in your life.
While it’s easy to pinpoint other signature Lovato ballads as her most profoundly personal work, the fact that she got emotional while performing “Stone Cold” on Saturday Night Live in 2015 speaks volumes, given the significantly emotive nature of her discography. The song is her finest because it’s inarguably her best vocal performance: on top of leaning into soulful influences, Lovato’s high note on “Stone Cold” is quite impossible to put into words. So I won’t.