The Greatest Pop Star By Year: 1981-2023 (Updated Staff Picks)

(This list is a project that Billboard initially published in 2018, and which we’ve updated in some form every year since. In honor of our associated Greatest Pop Stars of the 21st Century list finally nearing its conclusion — we’re publishing our No. 2 essay today (Nov. 26), with No. 1 coming next Tuesday (Dec. 3) — we’re republishing the project, now updated until 2023, and in a more easily navigated form. Check it out here and come back next week for both the reveal of our No. 1 Greatest Pop Star of the 21st Century, and then the week after as we begin rolling out our picks for the Greatest Pop Star of 2024!)

Pop stardom is, in many ways, a competitive sport. Not one that demands a lone winner as justification for the whole enterprise, exactly, but one that still entrances those of us watching from the sidelines to see who’ll come out on top. Who’s No. 1 this week? Who outsold who? Who’s playing the biggest venues? Who’s racking up Grammys, BBMAs, VMAs? Listeners can love and admire their artists of choice without them winning these many mini-battles — but when they do, it provides the same rush as a home-team victory, since it still provides some measure of that most important validation in fandom: Our fav is better than your fav. 

Now, we here at Billboard obviously play no small part in the declaration of these victors, as success on our charts has long been one of the biggest measures by which pop stardom is sized and graded. But we also know that while chart success is an essential factor, pop stardom carries too many intangibles to be judged solely on any combination of numerical calculations. It’s not just hit singles and best-selling albums: It’s music videos, it’s live performances, it’s image, it’s headlines and controversy and cultural impact and overall ubiquity. It’s the answer to the question, “Could you have lived through this year without having an opinion on this artist?”

Of course, it’s a far more subjective assessment than simply which team scored more points by the final buzzer. But it’s a discussion that has long been ongoing for rappers, and now something our staffers and most trusted contributors have been working on for many months to bring it to the pop world — with our list of the greatest pop stars from each year since 1981. 

Now, understand that when we say “pop star,” we’re not just meaning solo artists in the classic triple-threat, top 40 dead-center mold of Madonna and Michael Jackson. Those two artists appear, of course, as do many of their most obvious acolytes. But we define “pop star” broadly enough for it to also encompass rappers and singer-songwriters, rock bands and R&B groups. As long as they were impactful and wide-reaching enough to have a profound impact on that vague concept we know as the mainstream — and even more amorphously, the culture — they’re up for consideration here. 

Why 1981 as a starting point? Well, gotta start somewhere, and ‘81 was the year that forever changed modern stardom, with the premiere of MTV cementing the music video as an elemental factor in pop iconicity. Though its true impact on the top 40 landscape wouldn’t really be felt for a couple years after its debut, videos forever changed the scale of pop stardom, making the biggest artists three-dimensional figures, as present in our lives as our favorite sitcom stars and talk show hosts, if not more so. The new competitive landscape of MTV rotation forced them to think bigger, to try harder — and from Janet to Alanis to Rihanna to Drake, it’s impossible to envision the past 40-plus years of pop stardom without its impact. 

And what does “greatest” mean, exactly? Well, it’s not exactly “most popular,” though that’s certainly a large part of it. And it’s definitely not our personal favorites, strictly speaking — we love these artists, but this wasn’t the place for any of us to stump for our Should Be Bigger pet causes. Mostly, we’re looking for the pop star that best defines each year; the one whose impact was most deeply felt across the most spaces. How much of the year the artist is active for also matters: For instance, Taylor Swift might have released 1989 in 2014, but the album didn’t drop until October — so she’s more likely to be in play for 2015, when the set spun off most of its hit singles and videos and she spent most of the year on her victory lap world tour. 

Of course, our perception of pop stardom is unavoidably colored by personal experience — and our decidedly North American perspective — and you might very well see some of our picks and think that based on your own memories, we couldn’t be more wrong. Totally fair: We’ve done the best we could with the objective stats and the emotional reactions we all have, but several of these come down to coin-flip situations where we had to just sigh and go with our gut. To acknowledge some of the artists we passed over, though, we’ve also included some honorable mentions for each year — along with awarding rookie of the year (for emerging pop stars then still new to the mainstream) and comeback of the year (for veteran stars who had their first big year in a while) distinctions for each year. 

Read on below to find our essays attempting to justify our picks for each year — along with a handful of sidebar discussions that we couldn’t get to in our primary pieces — and feel free to let us know how we did your favorite artist wrong. Do try to remember, though: In pop music as in sports, there’s always next year.