Billboard’s Greatest Pop Stars of the 21st Century: No. 9 — Ariana Grande

17 October, 2024

With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. You can see the stars who have made our list so far here, and now we remember the century in Ariana Grande — whose standard-defying approach to pop music saw her withstand expectations and stigma to become one of the most prolific examples of what pop sovereignty can look like in the streaming era.

It’s easy to view Ariana Grande’s rise to the highest echelons of pop stardom as a classic, uncomplicated success story within the music business. The child-actor-turned-pop-sensation route is well-trodden, after all, and at first glance, the 31-year-old singer-songwriter appears to be yet another benefactor of that industry pipeline.

Yet once you dig further into her career, it becomes clear that her success was far from guaranteed. Over the course of the last decade-and-change, Grande created lasting hits amidst a mercurial musical landscape, endured unimaginable hardships and deftly navigated an industry that seemed to grow more volatile by the minute. Her standing today as a veritable icon is less a reflection of the efficacy of established systems that promoted her rise, and more a testament to her enduring, generational talent.

The star’s achievement came in part thanks to her drive for greatness from an early age. Born and raised in Boca Raton, Fla., Grande began her work towards a music career earlier than most — at age eight, she was already publicly performing on cruise ships, sporting events and her own personal YouTube channel, catching the attention of her family, her peers and even icons like Gloria Estefan. By the time she turned 13, the aspiring star had already booked her first professional gig as the bubbly, popular cheerleader Charlotte in the 2008 Broadway production of Jason Robert Brown’s musical 13.

Her foothold in the entertainment industry firmly established, Grande soon landed her breakthrough role as the loveable ditz Cat Valentine on Nickelodeon’s Victorious. With a sing-song voice proclaiming increasingly zany one-liners over the course of the show’s run, the character quickly rose among the ranks of the children’s network’s beloved characters — thanks, especially, to the impressive vocal chops Grande got to occasionally flaunt throughout the three season run. Valentine became so popular among the network’s fans that she earned her own spinoff series with iCarly’s Sam Puckett (Jennette McCurdy) on 2013’s Sam & Cat.

The standout support for her character provided a natural on-ramp to Grande’s own musical aspirations — who better than the perky-best-friend-type to deliver a string of uncomplicated pop songs? For her 2011 debut single “Put Your Hearts Up,” Grande and her team at Republic Records aimed to capitalize on that progression with a bubblegum anthem in the style of the day’s superstars like Katy Perry and Justin Bieber. But “Hearts” came and went, missing the Billboard charts and falling to bigger, bolder turbo-pop anthems of the era. Grande herself would later acknowledge that “Hearts Up” made more sense coming from her character than it did from her, making the entire experience feel “inauthentic and fake.”

So when it came time for her to reintroduce herself, Grande stepped away from the saccharine schtick of her Nickelodeon persona and leaned into her love of R&B. 2013’s “The Way,” featuring rising alt-hip-hop star Mac Miller, provided Grande with a streamlined, ebullient palette cleanser, placing the singer’s stratospheric four-octave range front and center. Vague, kid-friendly proclamations about giving a little love to change the world were exchanged for lyrics depicting a more mature, albeit still unspecific, approach to romance. Employing curated ‘90s sounds — including a lift of the central piano riff from Big Pun’s 1998 hit “Still Not a Player” — Grande happily aged herself up, gleefully drawing early comparisons between her airy, whistle-toned voice and The Voice, Mariah Carey. This, she told her eager fans, was the Ariana Grande she wanted to be.

Her audience certainly took that message to heart, earning the star her first of many top 10 debuts on the Hot 100. With “The Way,” Grande was ushered forth as a soon-to-be-star. Her subsequent debut album Yours Truly confirmed that “The Way” was the rule, not the exception — for every track on the record that didn’t quite work (like the doop-wop-meets-EDM strangeness of “Daydreamin’”), there was another that shined (the surefire R&B-pop killer “Piano” still stands out to this day), signaling the singer-songwriter’s vast potential in the pop space. With a No. 1 debut on Billboard 200, Yours Truly heralded the advent of Grande’s oncoming dominance.

Where 2013 saw Ariana arrive, the summer of 2014 saw her quickly start to take over. Her face adorned the covers of Billboard, Cosmopolitan and Teen Vogue, wherein she earnestly began to separate herself from her child star roots — never quite falling into the stereotypical “good girl gone bad” persona, but instead offering new context to buffer between the public’s introduction to her through Cat Valentine and the pop star she aimed to be. As her pop persona developed, so did her image; gone were the flame-red locks that defined her Nickelodeon career, replaced now by her natural brunette hair tied up in a stratospheric ponytail.

All the while, her music became utterly inescapable: “Problem,” her funk-fueled dance-pop diatribe featuring rapper-of-the-moment Iggy Azalea, dominated the airwaves in the early summer (bolstered in part by a whisper hook from her then-beau Big Sean); “Break Free,” her Zedd-produced EDM-pop anthem, gained steam shortly thereafter; and “Bang Bang,” her girlboss team-up with Jessie J and Nicki Minaj, exploded into the zeitgeist.

As each of her three singles peaked within the Hot 100’s top three slots at the end of August, Grande became the second woman in the history of the chart (alongside Adele) to maintain three tracks simultaneously in the top 10 as a lead artist. By the time Grande’s powerhouse sophomore LP My Everything arrived — along with its fourth-straight top-10 hit “Love Me Harder” featuring a then-lesser-known alt-R&B act called The Weeknd — the singer had already been ordained as the Next Big Thing in pop music, just one year after her debut album dropped.

With that attention came a predictable wave of controversy. Fans accused Grande of acting like a “diva” to her fans, with some drawing comparisons to her pop idol Mariah Carey. Rumors swirled of a feud with her Sam & Cat co-star Jennette McCurdy. A September 2014 headline in The Washington Post warned that the pop star was “on the brink of a major image problem,” stating that, as undeniable as Grande’s talent was, she was still a “very, very new name” in an industry with “a strange fascination with seeing the ‘fall’ of a newcomer as much as the ‘rise.’”

But nothing could have prepared us for one of the most deeply bizarre celebrity scandals of the 2010s — Donutgate. A leaked security video caught Grande licking a donut on display at a bakery in Lake Elsinore, Ca., while proclaiming that she “hates America” and kissing her backup dancer Ricky Alvarez. The public reaction came swiftly, with fans, pundits and industry professionals alike asking, what the hell is a rising star doing tonguing a donut she didn’t buy? A drop from Wikileaks would later reveal that even the Obama White House kept their distance, rejecting a proposal for Ariana to perform. The star made multiple apologies for the incident, assuring the public that her actions were those of a dumb kid, promising that “I’m going to learn from my mistakes.”

Still, it wasn’t until 2016’s flirtatious and sonically fluctuating Dangerous Woman that Grande faced diminishing returns. Its intended lead single “Focus” earned too little attention on the charts, and too much attention as a reskin of 2014’s “Problem,” that the label decided to cut it wholecloth from the album. The set became her first not to clinch the top spot on the Billboard 200, failing to dethrone Drake’s Views for its reign atop the chart. Critics, meanwhile, were divided over the album’s sound. Some praised the singer for taking a bolder, more daring approach to her established pop-n-b aesthetic, singling out the bombastic retro-soul title track “Dangerous Woman” and provocative reggae-pop Nicki Minaj duet “Side to Side.” Others heard the sound of a would-be superstar still struggling to figure out her sound three albums later.

A slight career dip certainly didn’t deter Grande from cementing her position as the pop star of the day. In March 2016, she served double duty as host and musical guest on SNL, poking fun at Donutgate; a few months later, she dazzled audiences with her spot-on impersonations of Christina Aguilera and Britney Spears on The Tonight Show; in September, she showcased her blissful romance with now-boyfriend Miller on his “My Favorite Part;” she even closed out the year on NBC’s telecast of Hairspray Live, playing the role of Penny Singleton alongside stage and screen stars like Jennifer Hudson, Harvey Fierstein and Martin Short. As she embarked on her second arena tour in 2017 — which would go on to gross $71 million, according to Billboard Boxscore — Grande appeared to be an unstoppable force.

Tragedy, as it turned out, is an immovable object. On May 22, 2017, minutes after Grande’s live performance concluded at the UK’s Manchester Arena, a terrorist detonated a suicide bomb in the arena’s foyer. 22 people were killed in the attack — twelve of whom were under the age of 16 — marking the deadliest act of terrorism on British soil since the 7/7 bombings of 2005. A public inquiry revealed in 2022 that more than 800 people were injured as a result of the attack. Grande escaped the attack physically unharmed, but emotionally “broken,” as she wrote in a tweet the day following the attack.

In the years to come, Grande would describe her experience with post-traumatic stress disorder following the attack, and the immense anxiety she suffered as a result. “I know those families and my fans, and everyone there experienced a tremendous amount of it as well … I shouldn’t even be talking about my own experience,” she told British Vogue. “I don’t think I’ll ever know how to talk about it and not cry.”

After successfully hosting her One Love Manchester benefit show — featuring artists including Justin Bieber, Katy Perry and Miley Cyrus to help raise over $13 million for the attack’s victims — Grande finished out the remainder of her postponed tour and retreated from the public eye. Where her Twitter and Instagram accounts were once littered with personal messages recounting her day-to-day experiences with fame, now there was a deafening silence.

Perhaps that’s why so many view “No Tears Left To Cry” as the turning point in Grande’s already impressive career. Over the course of three and a half minutes, the singer reset the narrative, acknowledging the abject horror she and her fans had been through while defiantly promising to move forward with light and optimism. House and disco stylings delivered the burst of joy she so earnestly sought on the track, bringing Grande’s vision for herself and her fans firmly into the forefront of the cultural consciousness. Yet what made “Tears” so remarkable was Ariana’s deft handling of tone: The song never comes across as a purely enthusiastic rallying cry, nor does it fit the mold of mournful reflections on loss — instead, Grande pulled off its own galvanizing message of picking it up and moving on.

With the album that followed, 2018’s Sweetener, Grande found something deeper than any of her past works. Albums like My Everything and Dangerous Woman took a kitchen-sink approach to finding what sounds produced hits, with Grande trying on new pop diva personas to best fit each package. Sweetener, by contrast, provided no artifice: It was just Ariana, the confessional, sometimes goofy, always-earnest singer-songwriter embracing the most vulnerable parts of herself. Though the album never quite achieved the level of chart domination exhibited during My Everything’s undeniable 2014 run, it exhibited an evolution, both artistic and personal, that once eluded Grande.

The album’s commercial success was certainly helped by the fact that Ariana had become the hottest topic in the months leading up to and following its release, thanks in no small part to her whirlwind romance with SNL star Pete Davidson. Tabloids, paparazzi, social media and the public at large were obsessed with the odd couple. When they were in public together, photos appeared online in seconds; when Ariana shared a one-minute interlude on Sweetener named after the comedian, articles appeared dissecting its romantic lyrics; and when the pop superstar bragged about her sudden fiancé’s “BDE,” fans turned it into a meme.

But a question arose from Sweetener’s shift — could Ariana Grande, Serious Artist coexist with Ariana Grande, Cultural Phenomenon? Within four months of the album’s release, a resounding answer crash-landed in the form of an out-of-nowhere, cycle-breaking single that smashed through Ariana’s own release pattern and her audience’s presuppositions. “Thank U, Next,” Grande’s cheeky response to the media storm around her breakup with Davidson and the death of her ex-boyfriend and collaborator Mac Miller, deftly toed the line between her blockbuster era and her newfound emotional honesty. Memes, think pieces, reviews and shot-by-shot analyses of its Mean Girls-inspired video poured out in the weeks to come, only further bolstered by the song’s No. 1 debut on the Hot 100 — somehow the first of the pop star’s career.

From that point forward, Grande became the invincible pop juggernaut that had been promised since her debut. The track’s follow-up — the Sound of Music-interpolating hip-hop jam “7 Rings” — immediately earned Grande her second No. 1; the release of her lauded fifth studio album Thank U, Next saw Ariana beat Cardi B’s record for the most simultaneous top 40 hits by a female artist. She even became the first solo artist in the history of the Hot 100 to simultaneously occupy the Nos. 1, 2 and 3 spots, and then the only act in 55 years to do so since The Beatles. Perhaps the most telling records that Grande managed to smash in 2019 came from Spotify: Upon its release, Thank U, Next shattered streaming giant Ed Sheeran’s record for the most weekly streams of any pop album, while within a year, Grande became the most streamed female artist on Spotify, surpassing pop superhero Rihanna.

Where Adele had revitalized the art of album sales in 2010, Grande became proof of concept at how the streaming era could generate gargantuan pop idols in the modern music business. Curating the social media experience for her army of Arianators over the course of her career paid dividends in Grande’s modern eras, as her loyal fan base rallied to support their fave at all costs, even as they occasionally crossed the line with comments about her image and personal life. She learned from the prolificacy of her hip-hop contemporaries like Drake that more was more when it came to content creation. Putting those two skills together, Grande became the artist to beat in the streaming game.

A global pandemic couldn’t even seem to stop Grande’s cultural takeover. A pair of early-lockdown collaborations — the retro-pop Justin Bieber duet “Stuck With U” and the French house Lady Gaga banger “Rain on Me” — earned Grande another pair of Hot 100-toppers. A year later, her sultry turn on renewed superstar The Weeknd’s “Save Your Tears” turned the slow-burning hit into an immediate chart-topper, sending the song to No. 1 on the Hot 100 within two weeks of its release. Even when her sixth LP Positions fell short of critics’ newly lofty expectations, she still took both the album and its title track to the summit of the Billboard 200 and Hot 100, respectively.

Today, even if her commercial power has waned from its 2019-2020 zenith, Grande has found a level of consistency amongst her cultural ubiquity. Eternal Sunshine, the singer’s sparkling meta-narrative on the pitfalls of public image, spawned yet another pair of No. 1 hits for the singer-songwriter, as well as earning a debut atop the Billboard 200. And as she gears up for her lifelong dream of playing Glinda in the long-awaited film adaptation of Wicked, it seems that Grande has come full circle, all the way back around to her theater roots.

Trace that ring from start to finish, and you’ll witness something fascinating; a young woman who managed not only to transform her pain into prosperity, but created a mold-breaking model for success. The career framework Grande built has only benefitted recent pop ingénues like Sabrina Carpenter and Tate McRae, who’ve capitalized on her streaming-focused strategies and sweetly melodic (and slyly winking) pop&B sound to rocket-launch their own music. Ariana Grande consciously changed how pop music is perceived and enjoyed by the masses, in a way a new generation of fans and artists will forever be so f–king grateful for.

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back Thursday as we reveal our No. 9 artist!