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The breakthrough stories in pop the past month have been few and far between, as Taylor Swift continues to rule the charts with her Life of a Showgirl album and its singles, and most artists have seemed largely content to stay out of her way. One exception is an artist who has been enjoying her greatest stateside successes the past few weeks, just below Swift’s stratosphere: Olivia Dean.

The U.K. singer-songwriter and BRIT School alum currently boasts four hits on the Billboard Hot 100 — her first four career entries on the chart — led by the ebullient “Man I Need,” which cracks the Hot 100’s top five for the first time on this week’s chart (dated Nov. 8). Meanwhile, her sophomore album The Art of Loving debuted at No. 8 on the Billboard 200 three weeks earlier, and has stayed in the top 10 each week since, holding at its No. 6 peak this week.

How has Dean managed this breakthrough? And what can she do for the rest of 2025 to ensure she makes the most of it? Billboard staffers discuss these questions and more below.

1. Olivia Dean’s “Man I Need” cracks the Billboard Hot 100 top five this week, moving 8-5. Why do you think the song has become such a breakthrough hit for her?  

Christopher Claxton: Olivia Dean has found a unique gap in music and filled it beautifully. Her sound has this timeless quality, it’s the kind of music you might imagine finding in your grandfather’s record collection, but she’s bringing it to a new generation, introducing Gen Z to classic, romantic sounds. She’s not chasing trends or virality; she’s carving out a legacy of her own. That freedom and authenticity is exactly when the magic happens. Her music feels both contemporary and timeless, which is why “Man I Need” has resonated so strongly and broken through to the top five. Kyle Denis: Outside of “Man I Need” being a really well-done and obviously catchy pop song, the song’s soulful foundation also allows it to benefit from the momentum R&B has seen on the Hot 100 in recent months. Of course, it also helps that the song’s TikTok teaser campaign ensured a voracious audience before its release, and her current opening slot on the final leg of Sabrina Carpenter’s Short n’ Sweet Tour certainly doesn’t hurt either.

Taylor Mims: Dean’s “Man I Need” has arrived just in time for cuffing season. The track has enough perky pop stylings to feel like we aren’t quite in winter yet, but Dean’s soulful voice is bringing us into a bundle-up Autumn when it is time to find a partner for the colder months. It is an earnest song about trying to find love and getting on the same page with a possible partner, timed perfectly for the season of commitment. 

Michael Saponara: What a fun, playful bop to invade the top five before 2025 ends. A pop piano blended with an earworm of a chorus, you can’t help but sing along and move your shoulders to Dean’s soothing vocals. It’s been intoxicating and I keep coming back for more with every listen. There are themes of yearning for a certain type of lover that everyone can just about relate to at any point in life. 

Andrew Unterberger: It just feels like it was the right song at the right time for Dean — I don’t think the song in itself is necessarily all that spectacular, but it’s charming in the ways she’s always charming, and clearly we were at a place where the public was ready to embrace her with open arms.

2. Meanwhile, three other songs are moving behind “Man” on the Hot 100: “So Easy (To Fall in Love)” (No. 43), “A Couple Minutes” (No. 87) and “Nice to Each Other” (No. 94). Do any of these songs feel like a second major hit for her?   Christopher Claxton: In my view, the songs most likely to become her next major hits aren’t necessarily reflected by the current chart positions. I’d rank them: “Nice to Each Other,” “So Easy (To Fall in Love),” and “A Couple Minutes.”

“Nice to Each Other” explores the idea of wanting to keep a romantic partner at a distance, but instead of feeling sad, it comes across as freeing, a track you can dance to. “So Easy (To Fall in Love)” is another song that’s immediately infectious and makes you want to move. “A Couple Minutes” isn’t quite a dance track, though it could work for a slow dance with someone special.Overall, none of these songs reinvent the wheel, but they’re far from boring or predictable. Olivia Dean has a way of making familiar themes feel fresh, which is part of what makes her music so compelling.

Kyle Denis: “So Easy” feels like a natural follow-up, it’s already the second-highest charting song from the album and it’s not too much of pivot sonically or thematically. 

Taylor Mims: “So Easy (To Fall in Love)” seems to be the natural follow up to “Man.” It seems to be gaining the most traction behind “Man” and has a similar enough sound to satisfy folks who are looking for a bit more. It is also upbeat and playful, so it can easily stand on its own to catch new listeners with lyrical content that still evokes cuffing season. The horn section also make the track feel a bit whimsical for a perfect holiday track.  

Michael Saponara: “So Easy (To Fall in Love)” feels like a natural fit for Dean’s next jazzy-pop hit. It’s sitting just outside the top 40 and with more and more eyes on her stateside, I could see Gen Z wrapping their arms around the bossa nova track, which radiates a breeziness that would brighten anyone’s darkest day. Amy Allen gets another notch in her belt on the songwriting side. 

Andrew Unterberger: “Nice to Each Other” feels like the logical song to me — and what a great music video — but it’s pretty clear that “So Easy” has the momentum at the moment. Still betting on the former, but hoping we have time and space for both to enjoy a nice moment in the sun. 3. While “Man I Need” breaks into the Hot 100’s top five this week, Dean’s The Art of Loving album remains one spot removed (No. 6) from doing the same on the Billboard 200. Do you think it’ll get there, or will it stay stuck just outside that region?   Christopher Claxton: The Art of Loving weaves together piano, strings and drums to create a sound that’s unmistakably Olivia Dean’s, while nodding to her neo-soul and Motown roots. I think the album has room to climb higher, especially as “Man I Need” rises on the Hot 100 and new tracks like “A Couple Minutes” make their debut on the chart this week. Fans will keep streaming the album, and with three songs now making waves, new listeners are likely to discover the tracks and, in turn, explore the album as a whole. I wouldn’t be surprised if it eventually breaks into the top five on the Billboard 200.

Kyle Denis: I definitely think it will get there. The current success of “Man I Need” and other album tracks keep the album afloat, and Olivia’s adult contemporary branding will prime her for the kind of demographic that actually buys music during the holiday season. And, of course, if she pops out with a Grammy nomination on Friday ahead of her SNL debut next week, the sky really is the limit for The Art of Loving. 

Taylor Mims: Based on Dean’s current trajectory, The Art of Loving will be in the top five in the coming weeks. Her other tracks are gaining traction, as is her jazzy, soulful sound. Plus, this Saturday she will be the musical guest on Saturday Night Live, which will undoubtedly draw plenty of new listeners and boost her numbers making her a shoe-in for the top five the week following. 

Michael Saponara: The arrow is clearly pointing up for Olivia Dean, and I expect her surge to continue into the year’s end. While there are plenty of music’s titans in front of her taking up real estate, I do think there will be a week where she sneaks into the top five. 

Andrew Unterberger: It’ll get there — possibly in the next couple weeks, possibly after the Christmas clear-out. But I can’t imagine this album is going away any time soon, so eventually the moment will be right for it to make that jump to the next tier.

4. At a time when few artists besides Taylor Swift are making major waves on the charts, Olivia Dean seems to have real things brewing. What do you think is the biggest factor behind her slow-building success?  

Christopher Claxton: I think the biggest factor behind Olivia Dean’s slow-building success is her ability to blend genres seamlessly. Neo-soul is in her blood, her mom introduced her to Lauryn Hill’s music, and Olivia’s middle name, Lauren, is actually a tribute to Hill. Beyond her influences, she tells a story with her music: from the first spark of a crush, to the anxiety and excitement of love, to heartbreak and reflection. Dean’s songs are highly relatable, yet they’re delivered through a sound that feels fresh and distinctive, which has helped her steadily gain traction on the charts. Kyle Denis: What fascinates me most about Olivia’s rise is how it both reflects and responds to shifts in the culture. 2024 felt like a year moving away from the cultural domination of pussy rap in the late ‘10s and early ‘20s and general sex positivity. Even if Sabrina got away with most of Short n’ Sweet, for example, her Man’s Best Friend album cover garnered a level of controversy that honestly felt overblown. While Dean is simply making the music she feels called to create, it doesn’t exist in a vacuum. When I read social media moment praising her “class” and “tastefulness,” often while disparaging more sex-forward performers, I can’t help but think about how the overall rise in American conservatism is explicitly and covertly shifting what we consume at the mainstream level. 

Taylor Mims: It sounds cheesy, but talent. In a time when we are seeing a lot of quick viral success off a song or two, Dean has been “brewing” for a while. The Art of Loving may be the breakthrough album, but she is on her second full-length album following 2023’s Messy, and has been slowly gaining traction for years rather than finding success overnight. A good opening slot on a major tour can do incredible things for a growing artist and Dean opened for U.K. star Sam Fender (and debuted on single “Rein Me In” with him) earlier this year, bringing her to the attention of a huge audience. Her talent did the work from there.

Michael Saponara: Artist development. Dean boasts a great lineage coming from the prestigious BRIT School that produced music deities like Adele and Amy Winehouse. At 26, she’s lived a little more life than some college-aged artists thrust into the spotlight. Dean’s clearly defined her lithe sound, which comes packaged with a distinct vision for her artistry. There’s more under the hood when it comes to the depths of her creativity, compared to some hitmakers, that appeals to different generations of listeners. It’s one thing to have a pink Instagram profile, compile likes on social media and hit the charts, and it’s another to pass the in-person test with flying colors. With the British singer opening for Sabrina Carpenter on the final leg of her U.S. Short n’ Sweet Tour, the sold-out crowds have made sure to be in their seats early (over an hour before Carpenter takes the stage) and truly engage with Dean’s performance, rather than scroll on their phones and treat an opening act like background noise. 

Andrew Unterberger: Her readiness. She reminds me of Sabrina Carpenter — who she’s even opened for on recent tour dates — in that everything she’s done since her breakout started earlier this year reflects someone who seems in all ways prepared for a moment like this: musically, professionally, personally. She looks comfortable in the spotlight, and so it’s not surprising that every release and appearance of hers appears to be drawing more fans into her world.

5. If you were part of Olivia Dean’s team, what would you advise her to do — if anything — in the year’s last couple months to take advantage of the momentum she’s currently building?

Christopher Claxton: I’d advise Olivia to capitalize on this momentum by doing as many interviews and social media connections as possible to keep engaging both new and existing fans. On top of that, dropping a 3-4 song Christmas EP featuring her signature, unique sound could be a smart move, something seasonal but unmistakably Olivia Dean, which could introduce her to even more listeners before the year ends. Kyle Denis: I think they’re doing everything perfectly. If anything, I’d start booking her for some holiday and year-end TV specials to help audiences continue to put a face to Olivia’s name. And start fielding names for a potential “Man I Need” remix! 

Taylor Mims: Saturday Night Live is a great next move. Following that, there should be wind in her sails and it is about keeping her top of mind as folks begin to retreat indoors. “So Easy (To Fall in Love)” is a logical next single to push, but “A Couple Minutes” feels like a smart turn. The track is already moving on the charts and resonating with fans, and has both dramatic and cinematic qualities to slow folks down during the hectic holiday months.  

Michael Saponara: Keep doing what they’re doing. Opening for Sabrina has been a great look as she continues to check boxes in her ascension to stardom across the pond. Having Dean on popular platforms that will only add to her visibility and further ingratiate her with the pop music scene is a more general suggestion I’d have. I love that she’s going to be performing on SNL in a couple of weeks. Whatever’s ahead in the next few months, you hope Dean’s rise is capped off by holding the Grammy trophy for best new artist on Feb. 1, and then the sky is the limit. 

Andrew Unterberger: Some artists do well to keep a low profile on the media front and build mystique through their inaccessibility. That is not Dean: She should be out there doing as many performances and making as many high-profile appearances as she feels comfortable with, making sure she has the chance to win over as many potential converts as she possibly can. Give her enough opportunities and she just might grab ’em all.