28 Best 2000s Singers, All Popular Music Artists

Norah Jones

Singer, songwriter, and pianist Norah Jones has sold more than 50 million records worldwide. The most crucial period in her career was undoubtedly the 2000s, as she was ultimately named the top jazz artist of the 2000s and made it to number 60 on Billboard’s artists of the 2000s chart.

Jones’ career would get a bit of a push after meeting and working with Peter Malick. Jones would go on to sign with Blue Note in New York City where she began to blaze her career trail.

In the 2000s, Jones would release Come Away with Me in 2002, Feels Like Home in 2004, Not Too Late in 2007, and The Fall in 2009.

Taylor Swift

I don’t think singer-songwriter Taylor Swift needs much of an introduction. Her songwriting career began at the tender age of 14, and by 2005 she had signed with Big Machine Records to become a country artist.

Her 2000s releases, Taylor Swift, and Fearless, of course, would be marked by the country-pop style that would propel her to superstardom.

I know people like to make a big deal about how artists reinvent themselves, but moving from country pop to pop is not a big leap by any stretch of the imagination, so let’s leave that part alone.

Swift would lay the foundations of her career in the 2000s, with “Teardrops On My Guitar,” “You Belong With Me,” and “Love Story” being some of her best from the time.

Sean Paul

Jamaican rapper, singer, and actor Sean Paul is among one of the most prolific artists in the genres of dancehall and reggae, with most of his albums being nominated for a Grammy Award for Best Reggae Album.

Paul would get his start in the mid-90s, collaborating with Jeremy Harding and gradually gaining local attention. His second album, Dutty Rock, would receive heavy airplay and rotation on BET and MTV.

His first single, “Gimme the Light,” would become an international hit, reaching number seven on the Billboard Hot 100.

Sean Paul would release Stage One, Dutty Rock, The Trinity, and Imperial Blaze, all in the 2000s.

Amy Winehouse

English singer and songwriter Amy Winehouse would, unfortunately, be one of a handful of famous musicians whose life would be tragically cut short. She would join the likes of Kurt Cobain, Jimi Hendrix, and Jim Morrison in the 27 Club in 2011.

The Amy Winehouse effect, for better or for worse, is like that of a religious martyr figure, and modern artists – especially English and Irish singers but also Australian, American, and Canadian singers – owe a great deal to her singing style.

Think Lewis Capaldi, Adele, Sam Smith, James Arthur, Dean Lewis, James Bay, Tones and I, and Shawn Mendes, among many others.

If you need to study up again, see “In My Bed,” “What Is It About Men,” “Stronger Than Me,” “You Know I’m No Good,” “Rehab,” and “Tears Dry On Their Own.”

Christina Aguilera

Singer, songwriter, actress, and TV personality Christina “Voice of a Generation” Aguilera rose to fame in 1999 with her debut album with familiar singles like “Genie in a Bottle” and “What a Girl Wants.”

Effectively, in the 2000s, her career was just beginning. Aguilera would release Mi Reflejo, My Kind of Christmas, Stripped, and Back to Basics, of which Stripped was probably the most influential and telling of future career moves as well.

See “Beautiful,” “Stripped,” “Can’t Hold Us Down,” and the sizzling hot “Dirrty.”

Chester Bennington

Best known as the lead singer of emo-drenched hybrid nu-metal rock band Linkin Park, singer Chester Bennington demonstrated that as a vocalist he could go from gentle to screaming at the drop of a pin.

Before Linkin Park, Bennington had stints with Sean Dowdell and His Friends? As well as Grey Daze. Bennington nearly quit music altogether before Zomba Music A&R rep Jeff Blue set up an audition for him with Xero, the band that would eventually become Linkin Park.

The band spent the better part of five years working on their debut album, Hybrid Theory, but their effort paid off, as the album went on to sell more than 4.8 million copies in its debut year (of 2000) alone.

A case could certainly be made that Hybrid Theory represented some of their strongest work, but the Park would also release Meteora in 2003, and Minutes to Midnight in 2007.

If you need a refresher, see “In the End,” “One Step Closer,” “Crawling,” “Bleed It Out,” and “Numb.”

Madonna

As the highest-grossing female artist worldwide, singer, songwriter, and actress Madonna hardly needs an introduction. Some might think her highest period of production was in the 80s and 90s, but she has remained very relevant through the 2000s, 2010s, and even into the 2020s.

In the 2000s, we would see the release of four studio albums – Music, American Life, Confessions on a Dance Floor, and Hard Candy.

All her releases did well, but 2005’s Confessions on a Dance Floor was a huge winner, and her Confessions Tour would become the highest-grossing for a female artist at the time. You might recall “Hung Up,” “Sorry,” “Get Together,” and “Jump.”

Gwen Stefani

There was a time when Gwen Stefani was best known as the lead singer of No Doubt, I’m not sure that’s the case anymore. If she’d reached the stratosphere with No Doubt, her solo career sent her straight through the stratosphere in the 2000s.

No Doubt would still release Return of Saturn in 2000 and Rock Steady in 2001, but the band would go on hiatus shortly after, prompting Stefani to embark upon a solo career in 2004.

Her debut studio album, Love. Angel. Music. Baby. Would spawn multiple recognizable hits, including “Hollaback Girl,” “What You Waiting For?,” “Rich Girl,” and “Cool.”

Her second solo album, The Sweet Escape, also did all right for her.

Kelly Clarkson

Having won the first season of American Idol, singer, songwriter, author, and TV personality Kelly Clarkson would rise to fame in 2002. Her debut single, “A Moment Like This,” would rise to the top of the US Billboard Hot 100 and was even the country’s best-selling single of the year.

Her 2003 debut, Thankful, was soon to follow and it debuted at the top of the Billboard 200 chart.

Clarkson decided that she wanted a new image, though, so she would go pop rock with her 2004 release, Breakaway, which spawned multiple hits, like “Since U Been Gone,” “Behind These Hazel Eyes,” and “Because of You.”

Her career would get off to a running start, and she would follow up with two additional albums in the 2000s – My December, and All I Ever Wanted. Clarkson’s release schedule remains steady and consistent to this day.

Michael Bublé

Canadian singer and songwriter Michael Bublé has helped renew public interest in traditional pop standards and the Great American Songbook.

His debut album would make it into the top 10 in Canada and the United Kingdom in 2003. Subsequent releases would only help him expand his reach into the U.S. and Australia.

In his early career, he would release BaBalu in 2001 and Dream in 2002. 2003’s Michael Bublé would be his breakthrough, and in the 2000s, he would also release It’s Time, Caught in the Act, Call Me Irresponsible, and Crazy Love.

Some fantastic moments include “Fever,” “Cry Me a River,” “Me and Mrs. Jones,” “Lost,” “Save the Last Dance for Me,” “Sway,” “Everything,” “Home,” “Haven’t Met You Yet,” and “Feeling Good.”