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VOICE OVER: Rebecca Brayton
While some of these artists had other hits, they're best known for one song. For this list, we'll be looking at the best songs released between 2000 and 2009 that we still love today. Our countdown includes “Milkshake”, "Bad Day", “American Boy”, “Hit Em Up Style (Oops!)”, and more!

#20: “1985” (2004)

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Bowling for Soup 80s nostalgia was big in the 2000s, and no song capitalized on it better than this one by Bowling for Soup. A cover of Baltimore band SR-71’s song, “1985” mixes pop culture touchstones like John Hughes movies, Whitesnake, and Madonna with a character study about a woman pining for her youth and the years she can’t get back. It’s a perfectly relatable song, not just for people who miss the 80s but also for anyone who longs for their own good ol’ days. Can we expect a hit song called “2004” that name-drops Bowling for Soup in a few years?

#19: “Boston” (2006)

Augustana When a relationship ends, it can be hard to understand what happened, especially if you didn’t initiate it. On “Boston,” San Diego band Augustana largely write from the perspective of the person cutting ties, explaining that their current relationship and current surroundings just aren’t good for them. Lead singer Dan Layus sings and plays piano with equal intensity, and by the end of the song, you understand his hurt as well as his acceptance of these new circumstances. What we want to know is how they got all of those pianos on the beach for the music video.

#18: “Milkshake” (2003)

Kelis Call it a hunch, but we don’t think Kelis was singing about an actual milkshake in this song. What exactly “[her] milkshake” is referring to is up for debate, but it’s clearly something irresistible, much like the song itself. Produced by The Neptunes, “Milkshake” manages to be playfully raunchy without ever crossing the boundaries of good taste or radio airplay. Kelis’ confident performance also surely influenced many contemporary R&B artists singing about the naughtier side of life. If you want to get people shakin’ on the dancefloor, put it on. This song? It’s better than yours.

#17: “Whine Up” (2007)

Kat DeLuna feat. Elephant Man A great debut single is a way to show the world just how much you have to offer. R&B singer Kat DeLuna did exactly that on “Whine Up,” an addictive banger about trying to seduce someone with every ounce of energy you can muster. The blaring beat is the perfect match for DeLuna’s vocals, which could fill a room on their own. She also performs a rap in Spanish, and Jamaican artist Elephant Man comes through with his own verse to keep the momentum going. With dancehall enjoying such prominence lately, there’s never been a better time to get down with “Whine Up.”

#16: “All the Things She Said” (2002)

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t.A.T.u. Some songs garner attention not only for their musical content but also for their thematic elements. Russian pop duo t.a.T.u. attracted plenty of controversy for their early 2000s single “All the Things She Said,” which deals with same-sex attraction between two teenage girls, at a time when such a topic was far more taboo. Some found the song and its video to be exploitative, being more about profiting off of gimmicks than about promoting love. But it also showed you could sing about topics that were previously considered off-limits and have a hit. Nearly 20 years later, and this song is still running through our heads.

#15: “American Boy” (2008)

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Estelle feat. Kanye West Even if you live in the places Estelle mentions on “American Boy,” like California and New York, her enthusiasm about them can easily rub off on you. The London singer created a multi-layered love song, showing affection both towards the titular American traveler as well as to everything he has to show her. The modern disco-funk sound is as fresh now as it was then, and along with Estelle’s sweet vocals, we also get a great self-deprecating feature from Kanye West, with plenty of British slang sprinkled in. We can all pledge allegiance to this song.

#14: “I Don't Wanna Know” (2004)

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Mario Winans feat. Enya & P. Diddy Like the Fugees before him with “Ready or Not,” Mario Winans created a hit based on a sample of Enya’s “Boadicea.” “I Don’t Wanna Know” takes a sad R&B ballad about infidelity and upgrades it with hard-hitting production that underlines the hurt Winans is feeling. Puff Daddy - then known as “P. Diddy” - comes through with his own message towards a former lover. But it’s Winans and his heartbroken delivery that will really have you in your feelings. If you’ve ever been afraid to come to terms with what you know is true, this song knows exactly how you feel.

#13: “Bulletproof” (2009)

La Roux Even more than “1985,” “Bulletproof” just screams “80s.” Specifically, it harkens back to a time when everyone on the charts was discovering synthesizers. Electropop duo La Roux’s hit song is full of retro delights that sound timeless when you consider how popular they’ve remained, like bouncy choruses and vocoder usage. But it’s not just production gimmicks that made this such an enduring song. There’s also the always-relevant message of moving on from a bad relationship and learning to love yourself. Want to feel bulletproof yourself? Just put on this song and watch as your confidence grows.

#12: “Collide” (2004)

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Howie Day Popular songs tend to be a little all-or-nothing when it comes to love. Either a relationship is perfect or it’s broken beyond repair. On “Collide,” singer-songwriter Howie Day finds a more realistic balance. Both he and his partner have their differences and have had their difficulties. But somehow, they find a way because their love for each other transcends these conflicts. “Collide” certainly has a heavy heart, but it also has hope that things will work out for the best. It shows that while love is certainly complicated, that doesn’t have to be a bad thing.

#11: “Teenage Dirtbag” (2000)

Wheatus Pining for someone who doesn’t seem to know you exist is a universally relatable experience, especially when you’re in high school. On “Teenage Dirtbag,” Wheatus gives a first-person account of someone with an unrequited crush on a popular girl. But one fateful prom night encounter changes everything and perhaps gave hope to other self-proclaimed “teenage dirtbags” trying to find their own Iron Maiden-loving sweetheart. With its sing-along chorus and catchy riffs, “Teenage Dirtbag” lets you feel the joys of angst all over again. Bucket hats might not always be in style, but this song hopefully will.

#10: “Absolutely (Story of a Girl)” (2000)

Nine Days You know a song means business when it launches into the chorus right at the beginning. And frankly, hearing the chorus once is all it takes for it to get stuck in your head. This was a massive, worldwide hit that is still an incredibly catchy time capsule with the power to take you back to the era of cargo pants and TRL. The sweet, upbeat pop-rock anthem was written by guitarist/vocalist John Hampson about his wife, who he was dating at the time. These days, John Hampson is a middle school English teacher, but even if his days as a rock star are over, their song still lives on, gracing countless karaoke bars worldwide.

#9: “Smooth Criminal” (2001)

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Alien Ant Farm Covering Michael Jackson is a pretty bold move for any artist to attempt, especially a song as well known as “Smooth Criminal.” But what makes Alien Ant Farm’s version work so well is that they don’t just try to replicate Jackson’s original. Instead, the California band updated “Smooth Criminal” for the 2000s, making it the nu-metal anthem we never knew it could become. They might not have made it quite as big as the King of Pop himself. But with “Smooth Criminal,” Alien Ant Farm provided us with a great version of an already-great song.

#8: “Wherever You Will Go” (2001)

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The Calling The Calling frontman Alex Band wasn’t even 20 years old when “Wherever You Will Go” was released, but his gravelly voice and sensitive lyrics suggest someone with at least twice as much life experience. “Wherever You Will Go” is one of the decade’s most impactful debut rock singles, a passionate ballad about being devoted to another person with every fiber of your being. It might seem a little over-the-top, but it speaks to the emotional intensity of love. If there’s someone in your life you feel a special attachment to, you probably love this song.

#7: “Never Leave You (Uh Oooh, Uh Oooh)” (2003)

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Lumidee Featuring a modified version of the iconic Diwali riddim, Lumidee’s debut single was a perfect blend of R&B and Dancehall. It climbed to #3 on the Billboard Hot 100, charted all around the world, and brought countless people out on the dance floor. Lumidee’s voice was put to perfect use on this song. It perfectly captures the mood of a breezy, fun block party or summer barbeque. All these years later, it can still effortlessly get people to sing and dance along to it.

#6: “Hit Em Up Style (Oops!)” (2001)

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Blu Cantrell It’s hard to say why, but revenge certainly seems to inspire a lot of great music. And listeners are attracted to the drama like moths to a flame. Because of that, it’s not surprising that a song about a woman who decides to get payback on a cheating lover by hitting him where it hurts (his wallet) became a huge hit. It certainly helped that it was an instantly catchy, incredibly well-crafted song that you can’t help but sing along to. And Blu Cantrell’s sultry yet fed-up vocals really sold the narrative to make the song irresistible.

#5: “I Believe in a Thing Called Love” (2003)

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The Darkness To this day, it’s hard to know if this song is serious or not. The ridiculously over-the-top video certainly didn’t help. But its success was undeniable. The band’s unabashedly retro style and lead singer Justin Hawkins’ falsetto vocals made a surprisingly potent mix that seemingly no one could resist. It had people singing along even as they scratched their heads. It also turned the band into bonafide rock gods, at least for a little while. The song appeared in movies, video games, was covered on “Glee,” and Taylor Swift sang along to it in a commercial for Apple Music. It’s still fondly remembered as a testament to a bygone era when guitars ruled the world.

#4: “Stacy’s Mom” (2003)

Fountains of Wayne Blending new wave and power pop, this band crafted a timeless classic that’s as catchy and fresh today as when it came out. Although the song was clearly indebted to bands like the Cars, Fountains of Wayne made a song that was all their own and just as memorable. Its massive success was undoubtedly helped by a music video that was every bit as iconic. Filled with pop culture references and a humorous and endearing narrative, it became a mainstay on both MTV and VH1. The song earned the band two Grammy nominations and broke them through to the mainstream. Even today, this perfectly constructed piece of ear candy is still likely to get listeners singing about Stacy’s mom.

#3: “Bad Day” (2005)

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Daniel Powter Both incredibly catchy and undeniably relatable, this power ballad still serves as a perfect soundtrack for someone having a rough day. It’s a simple but incredibly infectious song that really does have the power to brighten up someone’s mood. And as a sure sign of the song’s ubiquity, Weird Al actually wanted to parody it; unfortunately, Powter turned down the proposal. The song was also used to send off contestants on the fifth season of “American Idol,” and it became the biggest single of 2006. Daniel Powter, himself, was reportedly not much of a fan of the song, but hopefully, he can take solace in the fact that he created something with universal appeal that’s still beloved to this day.

#2: “Crazy” (2006)

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Gnarls Barkley Do you remember when you lost your mind? Specifically, do you remember when you first heard this song? Gnarls Barkley arrived with an impressive pedigree, bringing together vocalist CeeLo Green and producer Danger Mouse. But if expectations were high for the collaboration, the duo arguably surpassed them in one song. “Crazy” takes familiar soul and funk elements like crooning vocals and bouncing basslines and gives them a new kind of haunting energy. And moments like the strings in the chorus add even more atmosphere. You could hear it in any decade and it would always sound fresh. You’re not crazy if you love this.

#1: “A Thousand Miles” (2002)

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Vanessa Carlton Sometimes a song comes along that both captures a moment in time and feels absolutely timeless. And that’s precisely what Vanessa Carlton’s debut single does. As soon as the simple and beautifully iconic piano intro starts, it transports you back to 2002 but still manages to feel incredibly fresh. If the song came out today, it would feel right at home on the radio and most likely still be a smash. Instead of dominating MTV, it would soundtrack a million Tik Tok challenges. The song climbed all the way to #5 on the Billboard hot 100 and was the sixth most-played radio single of 2002. And even two decades later, it still holds a special place in listeners’ hearts.

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