Billboard Top Women Artists of the 21st Century Chart

Reinforcing the amount of star power ahead, five women combine to begin the countdown. The made-on-TV group, formed in 2005 on the MTV reality competition series Making the Band, scored back-to-back No. 1 debuts on the Billboard 200 with its first two releases: 2006’s self-titled set and 2008’s Welcome to the Dollhouse. In turn, the quintet – initially comprising Shannon Bex, Aundrea Fimbres, Aubrey O’Day, Dawn Richard and D. Woods – became the first female group to debut at No. 1 with its first two albums. The act scored a Hot 100 top 10-charting hit from each set, reaching No. 8 with “Show Stopper” in 2006 and the No. 10-peaking “Damaged” in 2008. –KEITH CAULFIELD

The early 2000s brought a new wave of women singer-songwriters to Billboard’s charts, following the Lilith Fair era in the 1990s that was headlined by the likes of Sarah McLachlan, Jewel and others. While guitar was a common through line, Carlton made piano especially prominent on her signature hit, “A Thousand Miles,” which traveled to No. 5 on the Hot 100 in 2002. It also topped the Pop Airplay and Adult Contemporary charts. Plus, parent album Be Not Nobody likewise reached No. 5 on the Billboard 200, marking her first of four LPs that she logged on the list through 2011. –GARY TRUST

Like many of the early American Idol champions, third-season winner Fantasia began her career in the best possible way, debuting at No. 1 on the Hot 100 with her first single, “I Believe.” The singer’s contemporary R&B production and classic impassioned vocals, best encapsulated with her signature yeaaaahhhh growl, positioned her for steady success. Her debut album, 2004’s Free Yourself, opened at No. 8 on the Billboard 200 and yielded three Hot 100 hits: “Truth Is” (No. 21), “Baby Mama” and the title track. Four more top 20 albums and another pair of Hot 100 hits followed, while the Grammy Award winner remains a force on the Adult R&B Airplay chart, with a dozen top 10 hits at the format. –TREVOR ANDERSON

There are only five all-women groups on Billboard’s Top Women Artists of the 21st Century retrospective, and four of them made most of their chart impact in the first decade of the 2000s. That means that Fifth Harmony is the newest such act, having debuted on the Hot 100 and Billboard 200 in 2013. Its momentum, and faithful fanbase, built over the mid-2010s, reaching a chart apex when “Work From Home,” featuring Ty Dolla $ign, and its parent album, 7/27, each hit No. 4. The group’s résumé includes three other top 10 albums and seven more Hot 100 hits, while its legacy extends to its members’ solo projects, including top 10 singles for Camilla Cabello and Normani. –ERIC FRANKENBERG

After debuting on Billboard’s charts in 1985, the band Sade – fronted by Nigerian-British singer-songwriter Sade Adu – continued its hitmaking run into the 2000s. The act’s Lovers Rock was released in 2000 and marked the group’s first studio album since 1992. Then came 2010’s Soldier of Love, which became the ensemble’s second No. 1 on the Billboard 200 (after 1986’s Promise) and first to bow atop the list. Sade last released 2011’s best-of set The Ultimate Collection, and last toured that year. When Billboard caught up with Adu in the midst of that trek, the possibility of another tour was seemingly the last thing on her mind. “I have absolutely no idea what the future holds,” she said. “It’s a miracle to me we are here now. I just know I will look back on it and feel good.” –K.C.

A constant for Charli XCX has been reinvention. She broke into the mainstream via memorable guest appearances on Icona Pop’s “I Love It” and Iggy Azalea’s “Fancy,” the latter of which spent seven weeks at No. 1 on the Hot 100 in 2014. She soon returned to the top 10 with her own pure-pop single “Boom Clap.” Over the last decade, she built a reputation for releasing boundary-pushing albums to critical acclaim – but it was last year’s Brat that sent her to new highs. The set reached No. 3 on the Billboard 200 in June, becoming her highest-charting LP, and marked one of the year’s defining albums. Six of the collection’s tracks charted on the Hot 100, including collaborations with Billie Eilish, Ariana Grande and Lorde, solidifying Charli XCX as one of pop and dance music’s most influential voices. –XANDER ZELLNER

Freshly freed from professional misfortunes that centered on a bankruptcy filing and lawsuit against her record label, Toni Braxton swept into the new century with a new contract and new sounds. What didn’t change, however, were her results. Teaming with producer Darkchild, the diva’s first offering of 2000, the saucy “He Wasn’t Man Enough,” shot to No. 2 on the Hot 100 and extended the run of form that put Braxton among the most successful singers of the 1990s. While the track marked Braxton’s biggest singles highlight of the era, the hitmaker landed nine new albums on the Billboard 200 over 2000-20, displaying her range through works of contemporary tunes (Pulse and Libra, for example), holiday fare (Snowflakes) and vintage R&B with her self-described “musical husband,” Babyface (Love, Marriage and Divorce). –T.A.

Lee’s status as one of Billboard’s 100 top-performing women in the 21st century dates to 1944, when she was born, fittingly during Christmastime. After making charts from the late ‘50s through the early ‘90s – and logging three Hot 100 No. 1s among 13 top 10s in the ‘60s – the 2000s have amplified her legacy, largely thanks to her 1958 holiday classic, “Rockin’ Around the Christmas Tree.” In December 2023, sparked by robust streaming counts, it hit No. 1 at last. Of recording the gift that keeps on giving, she recalled, “The producer cut the air way down in the studio. He had a big Christmas tree and everyone was there – the Anita Kerr Singers and the ‘A-team’ [of Nashville studio musicians], as we called them. It was like a little touch of magic kind of sprinkled in, and it turned out to be magic. It really did.” –G.T.

While the Queen Bee’s initial buzz came through The Notorious B.I.G.’s Junior M.A.F.I.A. crew, the sharp-tongued freestyler and fashion sensation elevated her empire at the turn of the century. Album releases became events, as her three consecutive top 10s on the Billboard 200 in the 2000s decade proved, and hit singles such as “The Jump Off” (featuring Mr. Cheeks) and “No Lighters” found love in the Hot 100’s top 40. The rapper’s real ace, however, was her knack for collaborations with her fellow A-listers. Nabbing 50 Cent for “Magic Stick” earned the pair a No. 2 hit in 2003; Kim and Missy Elliott hopped on Keyshia Cole’s “Let It Go” for a No. 7 smash in 2007; and she linked with Christina Aguilera on “Can’t Hold Us Down” to get to No. 12 in 2003. Ah, and we should mention that other Aguilera team-up, also with P!nk and Myá, the seismic 2001 “Lady Marmalade” cover that ruled the Hot 100 for five weeks. –T.A.

Alt/rock in the 2000s found a leading woman in Hayley Williams, vocalist for Paramore. The Tennessee-based band thrived on charts even after mostly ditching pop-punk in favor of forays into new wave, post-punk and more. Among its four Billboard 200 top 10s, the group reigned in 2013 with its self-titled set. Meanwhile, nearly seven years after initially cracking the Hot 100 with breakthrough hit “Misery Business,” Paramore reached the top 10 for the first time with “Ain’t It Fun,” in 2014. Eight years after that, the band crossed off another honor, ruling Alternative Airplay for the first time with “This Is Why.” –KEVIN RUTHERFORD

Rexha has conquered Billboard’s charts both as a writer and recording artist, spanning a variety of genres. She co-penned Eminem’s Rihanna-featuring “The Monster,” which topped the Hot 100 for four weeks in 2013-14. She has written five top 10s, also boasting artist credit on the other four, including her and Florida George Line’s “Meant To Be” – which dominated Hot Country Songs for a record 50 weeks in 2017-18. “I never thought that I’d have a pop/country crossover song,” she said in 2018. “That just goes to show you that all the best things are unexpected. My thing is going with feel and not creating any boundaries for myself.” –G.T.

Having arrived on Billboard’s charts in 1998, the silky-voiced Myá launched her sophomore era two years later and notched the best commercial stretch of her career. The classic confrontation anthem “Case of the Ex (Whatcha Gonna Do)” climbed to No. 2 on the Hot 100 in 2000, as parent LP Fear of Flying reached the top 20 on the Billboard 200 and spent a year on the chart. Myá soon bettered her runner-up status and captured the Hot 100’s top spot for five weeks in 2001 via a Grammy-winning cover of “Lady Marmalade,” with Christina Aguilera, P!nk and Lil’ Kim. The momentum fueled Myá to a third top 20 Hot 100 hit, among seven total chart entries during the quarter century, “My Love Is Like…Wo,” which reached No. 13 and helped her Moodring album peak at No. 3 on the Billboard 200. –T.A.

There are few acts as successful as Barbra Streisand, in both the pop consciousness and on Billboard’s rankings, with a deep catalog of hit albums and singles stretching back to her chart debut in 1963. In the first quarter of the 21st century, she logged eight top 10 sets on the Billboard 200, including a trio of No. 1s: Love Is the Answer (2009), Partners (2014) and Encore: Movie Partners Sing Broadway (2016). Incredibly, she’s the only act with No. 1 albums on the Billboard 200 in the 1960s, ‘70s, ‘80s, ‘90s, 2000s and ‘10s. Her storied chart career continued into the 2020s, when Release Me 2 debuted at No. 15 in 2021, making her the only woman with new top 20-charting (or even top 40-charting) albums in every decade from the ‘60s through the ‘20s. –K.C.

The Atlanta boom of the 2000s paid huge dividends for Keri Hilson, who started as a songwriter and backing vocalist before becoming the main attraction. Though she cracked the Hot 100 as a featured act on Xzhibit’s “Hey Now (Mean Muggin),” which peaked at No. 93 in 2004, you probably first heard her through her featured role on Timbaland’s “The Way I Are,” which surged to No. 3 in 2007. It set off a prolific stretch, with all of Hilson’s subsequent Hot 100 hits logged through 2011. Among the highlights: “Knock You Down,” featuring Kanye West and Ne-Yo (No. 3), the Lil Wayne-assisted “Energy” (No. 15) and the solo cut “Pretty Girl Rock” (No. 24). As her early tracks indicated, the singer’s sunny, smooth vocals often showed up for guest hooks, earning Hilson Hot 100 entries with hip-hop heavy hitters including T.I., Lil Wayne and Nas. –T.A.

Country music legend Reba McEntire, from McAlester, Okla., continued to earn honors in the first quarter of the 21st century, after first hitting Billboard’s charts in 1976. In 2011, she was inducted into the Country Music Hall of Fame, while in 2018 she received the esteemed Kennedy Center Honors for her lifetime of contributions to American culture. She also earned five of her 10 career top 10 albums on the Billboard 200 between 2007 and 2017. In 2011, “Turn on the Radio” topped Hot Country Songs, marking her 24th No. 1, second among women all-time only to Dolly Parton’s 25. Her most recent release, Not That Fancy, hit No. 25 on Top Country Albums in October 2023. –JIM ASKER

Amid recent is R&B dead? handwringing, Summer Walker’s chart standings answer that: nah.

Let’s review. Her debut album, 2019’s Over It, launched at No. 2 on the Billboard 200 and spent 272 weeks – more than five years – on the chart through the first quarter of the century. Its sequel, 2021’s Still Over It, avoided the sophomore slump by entering at No. 1 and marked the first R&B album by a woman to top the Billboard 200 in five years. More history came on the Hot 100, with the album generating 18 simultaneous hits, tying Walker with Taylor Swift for the most among women in a single week to that point. Given Walker’s limited support in traditional crossover routes, her success may surprise some, but her fanbase’s loyalty and demonstrated track record help prove that R&B is thriving. –T.A.

On her way to winning the 2018 Grammy for best new artist, Alessia Cara completed a six-month march to the Hot 100’s top five with “Here.” Meanwhile, parent album Know It All began its Billboard 200 run in 2015, at its No. 9 high, kicking off a 92-week residence on the ranking. Three more Hot 100 top 10s in 2017 further sparked her triumph on Music’s Biggest Night: “Scars to Your Beautiful” (No. 8), “Stay,” with Zedd (No. 7), and Logic’s “1-800-273-8255” (which helped increase calls to the National Suicide Prevention Lifeline), featuring Cara and Khalid. –E.F.

Branch broke through, at 17, on Billboard’s charts with three enduring pop/rock hits off her 2001 album The Spirit Room: “Everywhere,” “All You Wanted” – her first Hot 100 top 10 – and “Goodbye to You.”  She then reached the top five as the featured vocalist on Santana’s “The Game of Love.” She followed with 2003’s Hotel Paper and a country sojourn as half (with Jessica Harp) of The Wreckers, who crowned Hot Country Songs with “Leave the Pieces” in 2006. She added her own LPs Hopeless Romantic in 2017 and The Trouble With Fever in 2022, the latter a year after a 20th-anniversary rerecording of The Spirit Room. “I had not sat down and actually listened to The Spirit Room in so many years,” Branch mused in 2022. “[It] made me just so proud of what I did at that age.” –G.T.

Fronted by lead vocalist Kimberly Perry, the group from Jackson, Miss., arrived rounded out by siblings Reid (bass, vocals) and Neil (mandolin, vocals). Recognized immediately for Kimberly’s striking vocals and soaring harmonies from the brothers, the threesome crossed over with its sophomore single “If I Die Young,” written solely by Kimberly. It topped Hot Country Songs in 2010 and Adult Contemporary nearly a year later, while spending more than a year on the Hot 100. The group also banked two top five entries on the Billboard 200. Following a transition to pop in 2017, the act announced a hiatus in March 2023. Last month, The Band Perry returned, playing a Valentine’s Day show at the Grand Ole Opry (with family member Johnny Costello stepping in for Neil). –J.A.

While Fleetwood Mac released only two collections of new studio recordings in the first quarter of the 21st century (2003’s Say You Will and 2013’s Extended Play EP), the band continued to profit from the chart fortunes of earlier-released albums and new archival packages – nearly all featuring vocalists Christine McVie (who passed in 2022) and Stevie Nicks. The Rock & Roll Hall of Fame band’s classic chart-topping 1977 studio album Rumours spent nearly 500 weeks on the chart in 2000-24. The set found new generations of fans thanks to a Glee episode dedicated to the album in 2011, as well as a gone-viral TikTok in 2020 soundtracked to the album’s “Dreams.” So popular was that clip that it prompted a resurgence for “Dreams” on the Hot 100, where it surged to No. 12 – 43 years after it led the list. Meanwhile, Rumours raced to No. 7 on the Billboard 200 – its first top 10 placement in over 40 years.

When Billboard spoke to Nicks in 2020, she said she was “tinkled pink” by the revival of “Dreams,” sharing, “If the young kids start listening to Fleetwood Mac, start with the first album and just go through them. Sit down and be in it for the long run, and you’ll have the best time.” –K.C.

Considering Chappell Roan made her Billboard 200 album chart debut in April 2024 – less than nine months before the close of the eligibility period for this ranking – she made quite the impression in a short time. The singer-songwriter’s debut album, The Rise and Fall of a Midwest Princess, climbed to No. 2 on the chart in August, while the set spun off six charting hits on the Hot 100 before the close of 2024. She claimed her highest-charting Hot 100 hit to date with the non-album single “Good Luck, Babe!,” which peaked at No. 4 last September. Her successes on both lists helped the artist – and advocate for artists’ rights – finish 2024 as Billboard’s top new artist. –K.C.

A vocal powerhouse, the Medicine, Kan., native began her chart career in 1992, building a catalog of empowering anthems including 1994’s “Independence Day,” a fan favorite during her concerts since. She boasts five Hot Country Songs No. 1s among 20 top 10s – including half since 2000. Also in the first quarter of the 21st century, she tallied all seven of her Billboard 200 top 10s. Meanwhile, after winning the Country Music Association’s female vocalist of the year trophy in 1999, McBride scored the coveted honor again in 2002, 2003 and 2004. –J.A.

Simpson’s 2004 lip synch misstep on Saturday Night Live perhaps overshadows her success on Billboard’s charts in the mid-2000s. (Further key background: she was fighting vocal cord issues that night. She also took positives from the appearance: “Having to find at a young age that strength to be like, ‘I am good at this and I will keep going, and I will keep fighting’,” she said in 2024.) Simpson scored two No. 1 albums on the Billboard 200 – Autobiography (2004) and I Am Me (2005) – as well as the No. 4-peaking Bittersweet World (2008). Her biggest single, “Pieces of Me,” hit No. 5 on the Hot 100, as well as No. 1 for five weeks on Pop Airplay.

Notably, big sis Jessica is still ahead on this countdown; still, Ashlee can boast about her chart-topping performance on the Billboard 200, where Jessica hit a No. 2 high (among four top 10s, though, one more than Ashlee. So, like all good sibling rivalries, no definitive winner will likely ever be declared). –G.T.

Charts in the first decade of the 2000s made for fertile ground for American Idol contestants, a trend furthered by the show’s 2007 champion. Sparks logged a pair of top 10 albums on the Billboard 200 with her first two studio sets: her 2007 self-titled effort and 2009’s Battlefield. The former launched a pair of top 10s on the Hot 100 in “Tattoo” (No. 8) and “No Air,” with Chris Brown (No. 3). The latter single’s success on the list enabled the cut to close 2008 as the No. 6 biggest song on the year-end Hot 100 Songs ranking. Sparks scored a third top 10 on the Hot 100 with Battlefield’s title track, which reached No. 10 in 2009. –K.C.

When a then-47-year-old Susan Boyle stepped onto the stage of the U.K. TV reality competition Britain’s Got Talent for the first time in 2009, a meteoric rise to the top of the charts began for the big-voiced singer. Her audition performance – a cover of “I Dreamed a Dream,” from Les Misérables – went viral on YouTube, and previewed her debut album of the same name. The set premiered atop the Billboard 200 at the end of 2009, selling 701,000 copies in the U.S. in its first week – still the biggest opening frame for a female artist’s debut album since Luminate began tracking sales in 1991. I Dreamed a Dream spent six weeks at No. 1, and Boyle followed with six more charted releases through 2016, including two more top 10s: the No. 1 holiday set The Gift in 2010 and the No. 4-peaking Someone To Watch Over Me in 2011. –K.C.

Carly Rae Jepsen has a knack for writing irresistibly catchy pop songs. The Canadian skyrocketed on charts with 2012’s “Call Me Maybe,” a song so infectious that it not only spent nine weeks at No. 1 on the Hot 100 but also topped charts worldwide, cementing her status as a pop powerhouse. Jepsen returned to the top 10 once more, with follow-up “Good Time,” with Owl City, later in 2012. After such mainstream chart dominance, she has evolved into a beloved cult favorite among pop aficionados, selling out shows globally and consistently releasing critically acclaimed music. She has landed four albums in the top 20 of the Billboard 200, most recently The Loneliest Time in 2022. –X.Z.

Wilson roared into the country space with a massive first single, the proud, girlfriends-in-low-places anthem “Redneck Woman,” which dominated Hot Country Songs for five weeks. She followed with four additional top 10s. Wilson, from Pocahontas, Ill., sent three LPs to No. 1 on Top Country Albums in 2004-07, including All Jacked Up – which also launched atop the Billboard 200. She has won multiple awards including female vocalist of the year from both the Academy of Country Music and Country Music Association. Plus, the singer-songwriter took home a Grammy for best female country vocal performance for “Redneck Woman.”

“I remember sitting down and saying, ‘I can’t really relate to what I’m seeing on CMT, GAC all the popular music video channels, and this is not real life,’ ” Wilson recalled in 2024 of the John Rich co-write. “It was like, ‘If I’m not that, then what am I?’ And the best thing I could come up with was, ‘I’m just a regular ol’ redneck woman.’ That’s a really pivotal moment, just writing that song that I knew was uniquely me. But I also knew, from a songwriter’s standpoint, it was about as honest as I could get. I knew at the same time that it was going to speak to so many women that were feeling frustrated just like I was.” –J.A.

Hilary Duff was a multihyphenate teen idol of the early 2000s. Thanks to her role as Lizzie McGuire in the Disney Channel series, and The Lizzie McGuire Movie, she captured the hearts of young women around the world. Her success has since extended beyond television, as she’s made a lasting impact in music, film and pop culture. She charted five songs on the Hot 100 in 2003-07, including “Come Clean” and “So Yesterday” from her No. 1 Billboard 200 album Metamorphosis. She has charted five total top 10 sets, including another No. 1, Most Wanted, in 2005, before largely pivoting to memorable acting roles, including in Younger, How I Met Your Father and Gossip Girl. –X.Z.

Amy Winehouse boasts a brief history on the Hot 100: one top 10 hit – “Rehab” – a No. 77 peak for “You Know I’m No Good” and one posthumous week with Tony Bennett for 2011’s “Body and Soul.” And while a few collections of B-sides, demos and remixes impacted the Billboard 200 after her untimely 2011 passing, her short career’s presence on this recap is largely owed to Back to Black. The album debuted at No. 7 in March 2007, climbed to No. 6 that July and then to No. 2 the next year following five Grammy wins. It returned to the top 10 following her death and has lingered in the years since. Recorded in 2005, released in the U.K. in 2006 and in the U.S. in 2007, the set reentered the first Billboard 200 of 2025, reflecting her legacy and already impacting the survey’s next quarter-century. –E.F.

Lana Del Rey is riding an eight-album streak of full-length albums hitting the top 10 of the Billboard 200. Two hit No. 1: 2014’s Ultraviolence and 2017’s Lust for Life. Quite the pedigree for an alt-pop singer-songwriter whose smoky timbre has graced the Hot 100’s top 10 twice, first on Cedric Gervais’ dance redo of “Summertime Sadness” in 2013, the other as featured on Taylor Swift’s “Snow on the Beach” nearly a decade later. Her influence has touched many artists on this list, from pop to alternative to full-fledged rock, both as a songwriter and as a torchbearer of the moodier pop of the ‘10s. –K.R.

Iggy Azalea hadn’t touched the Hot 100 before 2014 but was one of its most reliable hitmakers by the end of that year. “Black Widow,” featuring Rita Ora, reached No. 3, following her own featured turn on Ariana Grande’s No. 2-peaking “Problem.” The latter would have topped the chart had it not been for Azalea’s breakout smash: with its Charli XCX hook and Clueless-inspired music video, “Fancy” was No. 1 for seven weeks and later named Billboard’s top song of the summer. The New Classic had the hits to back up its title, debuting at No. 3 on the Billboard 200, but she has largely let her legacy rest, having announced in 2024 that she sold her masters and no longer has an active record contract. –E.F.

A defining singer and commercial juggernaut of the 1980s and ‘90s, Whitney Houston began the new century on a victory lap with Whitney: The Greatest Hits, which debuted at No. 5 on the Billboard 200 in June 2000. Celebrations, however, slowed for much of the decade as her musical output shrank amid personal issues, but recovered in 2009 for a No. 1 album, I Look to You. Tragically, most of Houston’s brightest chart moments in recent years traced to the legend’s death in February 2012, which sparked a flurry of activity, including a No. 2 new peak for Greatest Hits and a No. 3 Hot 100 rebound for former chart-topper “I Will Always Love You” (which led for a then-record 14 weeks in 1992-93). The signature song lent its name to a second best-of collection, which became Houston’s longest-charting title on the Billboard 200, keeping Houston’s iconic voice alive across generations. –T.A.

Fittingly, the reach of Bedingfield’s 2006 smash “Unwritten” was at the time only just beginning. The song was then certainly a chart monster, hitting No. 5 on the Hot 100 and ruling Adult Contemporary for 11 weeks. Still, nearly 20 years later, it remains a pop culture staple, having hit No. 20 on the Billboard Global 200 chart in March 2024 amid a nearly year-long run on the ranking, thanks to its rediscovery among TikTokers and its evergreen lyrics about making one’s way in the world. Bedingfield went on to add a second No. 5 Hot 100 hit, “Pocketful of Sunshine,” in 2008, while the album of the same name reached No. 3 on the Billboard 200. –G.T.

As the First Lady of DMX’s Ruff Ryders crew, Eve has combined her charming swag and sharp-tongued bars to play with the top dogs on the charts – men or women. Popping onto the mainstream radar in 1999, her 2000s campaign started with a celebrated feature (also with guests Nas and Q-Tip) on a remix of Missy Elliott’s “Hot Boyz,” which cruised to No. 5 on the Hot 100 and achieved a then-record 18 weeks atop Hot Rap Songs. Another historic win narrowly eluded Eve, twice, as her Gwen Stefani-assisted “Let Me Blow Your Mind” and Alicia Keys-supported “Gangsta’ Lovin,” both peaked at No. 2 on the Hot 100; had either taken the top spot, the rapper would have been only the second female MC, after Lauryn Hill, to reach No. 1. Still, her stats remain undeniable, with 14 Hot 100 hits and four albums on the Billboard 200 in the first quarter of the century, even more impressive given that she’s released only one album, 2013’s Lip Lock, in the last 20 years. –T.A.

When Twain mania was at its zenith, the Canadian-born singer-songwriter served up Come On Over, which commanded 50 weeks at No. 1 on Top Country Albums in 1997-2000, the longest rule by a woman. The set also hit No. 2 on the Billboard 200. The turn of the century brought new chart heights, as Up! opened atop both rankings in December 2002, marking Twain’s first Billboard 200 leader. Nearly 15 years later, she ruled the all-genre list again with Now.

From Come On Over and Up! combined, Twain rang up 12 Hot Country Songs top 10s. “You can’t rush writing good songs,” she told Billboard in 2017. “I can only speak for myself, but it just felt like, for me, that it just takes longer to make a truly great album, if you want it to be that great.” –J.A.

Jessica Simpson’s debut Hot 100 hit, 1999’s soaring ballad “I Wanna Love You Forever,” hit a No. 3 high for five consecutive weeks. It was released as the lead single from Simpson’s debut album, Sweet Kisses, which spent more than a year on the Billboard 200, reaching No. 25. She became a regular visitor to the album chart’s top 10 after that, sending four sets to the top tier in 2001-08. She logged her highest-charting album with In This Skin (No. 2, March 2004), amid her run as a reality TV star on MTV’s Newlyweds: Nick and Jessica (2003-05), which chronicled the lives of her and then-husband Nick Lachey (of 98 Degrees). Following “I Wanna Love You Forever,” Simpson scored eight more Hot 100 hits through 2008, including six that reached the top 40 (or swam to the top 40, like tuna! Or flew, or walked all wobbly, like chicken?) –K.C.

Sara Bareilles has built a decades-long career that spans music, television and theater, crossing genres and transforming her into a global star. But if there is truly one song that defines her journey, it’s her debut breakthrough single, “Love Song.” Released in 2007, the track marked her first Billboard chart appearance, hitting No. 4 on the Hot 100 and topping Pop Airplay, Adult Pop Airplay and Adult Contemporary. The song introduced her to listeners who have since followed her through an ever-evolving career. She starred on Broadway in Waitress, Jesus Christ Superstar and Into The Woods and, proving her appeal knows no depths, earned a Tony nomination for scoring the SpongeBob SquarePants musical. –X.Z.

Barely five years since her debut, Megan Thee Stallion has sprinted to a level of mainstream success that has solidified her among the most lauded female rappers ever. With just her third Hot 100 hit, 2019’s “Hot Girl Summer” collab with Nicki Minaj and Ty Dolla $ign, she revealed a savvy for converting social media moments into chart payoffs when the viral phrase yielded a No. 11 Hot 100 single. That pipeline later struck gold through her three No. 1s: “Savage,” featuring Beyoncé and her feature on Cardi B’s “WAP” (both in 2020) and her “Hiss” diss (2024). Between the buzziest moments, she has remained a consistent hitmaker, with 40 Hot 100 entries and seven top 10 albums on the Billboard 200. –T.A.

Ellie Goulding started off her Hot 100 chart career with a bang, as her debut hit “Lights” reached No. 2 in August 2012, spent over a year on the list, and wrapped 2012 at No. 5 on the year-end Hot 100 Songs ranking.  But she didn’t stop there. The English singer-songwriter claimed another 13 hits on the Hot 100 before the close of 2024, including the No. 3-peaking hit “Love Me Like You Do” from Fifty Shades of Grey. Goulding also posted a pair of top 10 efforts on the Billboard 200: 2012’s Halcyon (No. 9) and 2015’s Delirium (No. 3). –K.C.

After first appearing on Billboard’s charts in 1989, Enya continued to be a force in the first quarter of the 21st century via her signature layered and lush brand of new age. She notched four Billboard 200 top 10s between 2001 and 2015 and also reached the chart with 2009’s The Very Best of Enya, the longest-leading title in the history of Billboard’s New Age Albums chart. In 2001, “Only Time” hit No. 10 on the Hot 100, connecting in the wake of the 9/11 attacks. Enya added a second Hot 100 top 10, in a featured role, in 2004, when Mario Winans’ “I Don’t Wanna Know” reached No. 2, thanks in part to its sample of her 1987 track “Boadicea.”

“I’ve always felt that success and fame are two different things, so I’ve never been a person to seek fame,” the Irish musician (born Eithne Pádraigín Ní Bhraonáin, or Enya Patricia Brennan) shared in a rare interview in 2016. “I love the success, the success of the music is very important to me, but the fame side of it is something that I feel other people enjoy. They do it so well. But I like to be able to get around without being recognized too much.” –G.T.