Olivia Dean was just named Apple Music’s 2026 Artist of the Year, and rightfully so.
Before Oliva entered the top 100 charts, my top artist every year was almost always Adele. People have made clear comparisons between the two artists’ work and themes, and I think it would be hard to argue against the similar, powerful nature of their discographies. Unlike Adele, however, I don’t have to cosplay as a 30-year-old divorced woman or pop star to fully experience the range of emotions offered in Dean’s songs.
That’s why I love Olivia Dean: Her music applies directly to love and life as a 20-something. Through her music, she defines and rewrites love, whether it’s romantic, platonic, or love for oneself.
As a former theater kid, I’m a sucker for a ballad, of which she has plenty, and I also need to feel music to like it. If I’m not emotionally hungover after listening to an album, I don’t replay it. Likewise, I love when an artist feels their music, and Oliva has a way of injecting her songs with clear and moving emotions.
Her musical style is also just fun and masterful. Olivia’s music spans soul, R&B, pop, and jazz to keep the sound interesting against already compelling narratives.
So, whether you are looking for a song to sing with your friend in the car, an angry cry about your situationship or ex-friend, or to bask in love, here are my top Olivia Dean recommendations.
“Out“
“Out” is from Olivia’s 2020 EP What Am I Going To Do On Sundays? I had listened to it from Olivia’s live stream concerts during the pandemic, but the first time I heard it on Apple Music, I stopped in my tracks. It’s one of those songs that makes you nauseous.
“Out” is a raw account of a relationship nearing its end, as the other person clearly loses their love for the other. It captures the hurt and growing agony of the situation against the decisive statement: “I won’t pretend that I can be just friends.”
“Touching Toes“
“Touching Toes” is a happy cry song. It captures the beauty of letting yourself fall in love “like the real stuff,” and finding a person that makes you love in a slap-happy, cliché way.
“Diamonds on the Soles of Her Shoes (Apple Music Sessions)“
Oliva Dean’s cover of Paul Simon’s “Diamonds on the Soles of Her Shoes” does something to me that I can’t explain. It’s my go-to pick-me-up listen.
In general, having a woman sing this song adds a beautiful layer to the lyrics and meaning of the song, and I think that’s what makes it so intoxicating.
“Let Alone The One You Love“
No, because, actually, who would you do that to a friend? Let alone the one you love?
If someone were tracking my very limited time on TikTok, I would say that 25% of it is spent watching videos from The Art of Loving Tour. Later in the tour, there were a few nights where Olivia got emotional during this performance that were authetically moving.
I know this is one of her more popular songs, but I would recommend listening to a live performance, especially if you were ever told that you were “too much” by someone you love.
“Ladies Room“
Truly a snippet from a conversation in the ladies’ room at a bar, as intended. “Ladies Room” is a song for the girls with insecure ex-boyfriends.
It’s a surprisingly upbeat song, almost to celebrate independence, but is centered around telling a man to get a grip. She clocks him: “You’re projecting, overstepping. No, I don’t have to choose. This is way less about me and way more about you. I love being in your space. Sometimes, I need some room.”
“It Isn’t Perfect, But It Might Be“
This song was featured in Bridget Jones: Mad About The Boy, and it definitely gives an upbeat romcom. Like a lot of the tracks on Messy, it’s about letting go while falling in love, and letting things be imperfect in order to fully fall. It’s the perfect soundtrack to add to your morning routine.
“Everybody’s Crazy“
As a severely anxious girl, this one is actually a sad and happy cry. It surrounds the emotional intimacy of a relationship, and how both people reveal their weaknesses and insecurities to one another and support each other through it.
If I had to choose a song right now to define love, this would be it.
“Dangerously Easy“
This song slows everything down a bit. It starts out lamenting an ex, asking how they found their way: How did they find happiness? And why couldn’t they find that happiness in their relationship?
It’s not bitter but rather reflective of all of the ways that the relationship couldn’t have worked. She doesn’t blame herself for the relationship’s demise, but ends the song, asking, “What do I have to do to make it [love] look easy- dangerously easy- like you?”
“I’ve Seen It“
I know that you have probably heard this song, but I encourage you to listen to it in the context of Olivia’s discography. It’s fitting that this is one of her most popular songs because I would argue that it’s the thesis for her work.
As her work progresses, Olivia’s definition of love softens and expands, but the theme throughout all of her songs is palpable: Even when it goes wrong or is unmet, love is inside of her, and she won’t compromise herself to get love from someone else.