These artists absolutely dominated the airwaves (and our MySpace accounts) 20 years ago, and since then, time has taken them in some interesting directions. Let’s check in:1. Akon
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Akon had a string of huge hits in the 2000s, including “Lonely,” “Smack That,” and “Right Now (Na Na Na).” Although he continued to release music over the years, in the last decade, he has focused on other projects, including the philanthropic Akon Lighting Africa organization, which provides solar energy in various African countries, as well as the now-abandoned Akon City — a planned futuristic city in Senegal that was supposed to operate on Akon’s own cryptocurrency, Akoin.
2. Sum 41
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Sum 41 formed in the ’90s and grew in popularity until they were everywhere in the 2000s, with hit songs like “In Too Deep” and “Fat Lip.” They went on to release more music but never quite hit the same level of fame, and they officially disbanded in March 2025. Lead singer Deryck Whibley released a memoir in 2024 and now runs a sock company. Meanwhile, former drummer Steve Jocz is now a YouTuber, bassist Jason McCaslin hosts his own radio show, and guitarist Dave Baksh has a merch company.
3. Outkast
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Outkast were hugely influential in the ’90s and ’00s, with hits like “Ms Jackson,” “So Fresh, So Clean,” “Hey Ya!,” and “Roses.” They split up in 2007 (although temporarily reunited in 2014) and have since pursued their own things. Big Boi has released a few solo albums over the years and also dabbled in acting, while André 3000 has been more shy of the spotlight, although still exploring a range of creative outlets, including acting and instrumental music.
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In the ’00s, Avril Lavigne was known for her heavy eyeliner and iconic songs like “Complicated,” “Sk8er Boi,” and “My Happy Ending.” She disappeared from the spotlight for a while — to the point that there was a whole conspiracy theory that she’d been replaced by a clone called Melissa — but she was actually recovering from Lyme disease. In recent years, she’s returned to music and touring.
5. Imogen Heap
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While Imogen Heap was at her most famous in the mid-’00s as the “Mmmm watcha say” singer, thanks to the iconic use of her song “Hide and Seek” on The OC and the subsequent “Dear Sister” parody on Saturday Night Live, she’s had a varied career. She’s steadily released music, including the toddler parent fave “The Happy Song,” as well as composing for projects like Harry Potter and the Cursed Child. In recent years, she’s shifted focus to exploring the use of technology, like blockchains and AI in music.
6. Gym Class Heroes
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The mid-’00s were huge for Gym Class Heroes, with some of their most popular songs coming from collabs with other 2000s icons like Patrick Stump (“Cupid’s Chokehold”) and Adam Levine (“Stereo Hearts”). They’ve been on hiatus for more than a decade and have all had much quieter careers since. Matt McGinley now works as a music producer for “This American Life” and also composed music for podcasts like “Serial” and “S-Town”, while Eric Roberts opened a restaurant. As a group, the guys have announced plans to reunite and make new music in 2026.
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7. Damien Rice
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Any emotional scene in the 2000s — whether it was on TV or in movies or just, you know, people’s own personal lives — was sure to have a Damien Rice soundtrack at some point, particularly songs like “The Blower’s Daughter” and “Cannonball” from his album O. Although more low-key, his music career has continued with new releases and touring, and in 2023 he embarked on a unique kind of tour — performing on a sailboat at various ports across Europe.
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Lily Allen was an it girl in the 2000s; her biggest musical hits include “Smile” “The Fear” and “Not Fair.” In the 2010s and 2020s, she continued to release music while also exploring other creative outlets, including acting, writing a memoir, creating a sex toy, hosting a podcast, and launching a foot-centric OnlyFans. Recently, she also had a high-profile marriage — and breakup — with Stranger Things actor David Harbour.
9. My Chemical Romance
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My Chemical Romance were THE face of the emo movement of the 2000s, especially with songs like “I’m Not Okay (I Promise)” and “Welcome to the Black Parade.” While the band broke up in 2013, they have reunited in recent years and toured together. They all stayed busy with other things in the meantime — frontman Gerard Way not only worked on other music, but he also started writing comics, including co-creating The Umbrella Academy and working on its Netflix adaptation. Mikey Way also shifted his focus to writing comics, while Ray Toro and Frank Iero continued to work in the music industry. Bob Bryar retired from the music industry in 2014 and became a real estate agent; he passed away in 2024. Since then, My Chemical Romance reunited and announced a 2026 world tour.
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10. Sean Kingston
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Sean Kingston was just a teen when his fame exploded in the ’00s thanks to his debut single “Beautiful Girls”. Although he continued to work in music, he also had personal difficulties and controversies — in 2011, he nearly died in a jet ski accident, and this year he was sentenced to three and a half years in prison for his role in a million-dollar fraud scheme with his mother.
11. Limp Bizkit
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Limp Bizkit rose to fame in the ’90s, and by the mid-’00s, they were so huge that they’d already released a greatest hits album, featuring songs like “Nookie,” “Rollin,'” and “Behind Blue Eyes.” The band then went on hiatus, but has since reunited and resumed touring. In the meantime, they have occasionally drawn attention for different things (both positive and negative). For instance, while Wes Borland, DJ Lethal, and John Otto explored other music projects, Sam Rivers went into producing, and Fred Durst moved into the film industry as both an actor and director — but he also got into legal trouble and drew controversy for his fascination with Russia and his admiration of Vladimir Putin.
12. Ben Lee
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Ben Lee had his biggest international hit with the album Awake Is the New Sleep and its singles “Gamble Everything for Love,” “Catch My Disease,” and “We’re All in This Together” in the mid-2000s. He has continued releasing music and is currently touring for the 20th anniversary of Awake Is the New Sleep, but took some interesting detours in the meantime — including getting caught up in a couple of cults and an MLM company with his wife, actor Ione Skye. The pair now co-hosts a podcast called Weirder Together.
13. Death Cab for Cutie
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Like any band featured on The OC soundtrack, Death Cab for Cutie had a huge moment in the mid-’00s, especially with songs like “Soul Meets Body,” “I Will Follow You into the Dark,” and “Transatlanticism.” They’ve continued to release new music, while frontman Ben Gibbard has also released solo music and become a passionate trail runner. During the pandemic, he also did daily livestream concerts from his home. Guitarist Dave Depper has also released solo music and become a runner, while drummer Jason McGerr opened his own recording studio and works as a drum teacher. Former guitarist Chris Walla left the group in 2014 and went on to release solo music and run his own recording studio.
14. Vitamin C
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As Vitamin C, singer Colleen Fitzpatrick became forever associated with graduation ceremonies thanks to her single “Graduation (Friends Forever),” which reached its peak of popularity in the early 2000s. She was an actor both before and after her time as Vitamin C (she even played Amber in the original Hairspray movie), but in the early 2010s, she became a music executive at Nickelodeon and later went on to work at Netflix. She also recorded a new version of “Graduation” for charity during the pandemic.
15. Fall Out Boy
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Thanks to songs like “Sugar, We’re Goin Down,” “Thnks fr th Mmrs,” and “This Ain’t a Scene, It’s an Arms Race,” Fall Out Boy were one of the biggest bands in the world in the 2000s. They went on hiatus in the late 2000s but reunited in 2013 and have since released new music and continued touring. The band members have also pursued various projects over the years, including running record labels and production companies, clothing lines, and nightclub chains, as well as delving into acting and writing endeavors.
16. Dido
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In the late ’90s and early ’00s, Dido was hugely popular in her own right through her singles like “Here with Me,” “Thank You,” and “White Flag,” but Eminem sampling “Thank You” on the culture-shifting song “Stan” exposed her to an even wider audience. During the 2010s, Dido largely stepped away from fame and touring to spend time with her family, although she’s continued to release new music occasionally and, more recently, began touring again.
17. Clay Aiken
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After coming second on American Idol in 2003, Clay Aiken released a bestselling album, Measure of a Man, and then found a strong niche doing Christmas music and specials. Over the years, he’s also acted and appeared on reality TV. Plus, he’s delved into politics, running for the US House of Representatives in North Carolina twice, in 2014 and 2022.
Which other artists from 20-plus years ago are you curious about? Share them in the comments!
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