25 Songs That Are STILL Good 25 Years Later
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VOICE OVER: Ryan Wild
Take a nostalgic journey through the musical landscape of 1999-2000 as we explore 25 iconic songs that have stood the test of time. From pop and rock to hip-hop and R&B, these tracks continue to resonate with listeners decades later, proving that great music is truly timeless. Our countdown features unforgettable hits from artists like Destiny's Child, Eminem, NSYNC, Britney Spears, and many more that defined the turn of the millennium and continue to be beloved today! Which of these movies do you think aged the best? Share in the comments.
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Welcome to WatchMojo and today we’re counting down our picks for 25 songs we’re listening to 25 years later. For this list we’ll be including songs that were released in 1999 but were popular in 2000.
While “Semi-Charmed Life” will probably always be their biggest song, “Never Let You Go” is a worthy listen. It really pulls you in, starting with its catchy guitar riff. It’s coupled wonderfully with the song’s lyrics. It builds nicely to the chorus which you can easily find yourself singing along with. It was well received by critics at the time of its release with praise for lead singer Stephan Jenkins’ vocals. The song was considered the standout track on the band’s second album, “Blue”. We definitely say we don’t want to let this song go.
This is the debut single from Ludacris and what a way to burst onto the scene. He would go on to have massive success in the following years but it all started with this track. Lyrically the song is all about sexual fantasies, so we can’t get into it as it is pretty explicit. But what we can say is that Ludacris brings it with his delivery and flow, especially with the stuttered delivery of the main hook. It’s a good introduction to Southern hip hop which has a distinctive flair from traditional hip hop.
What you may not realize is that this song's main riff was inspired by a Wu-Tang song. It’s got a deep driving hip hop beat that makes you want to move. Its drums are sampled from the jazz fusion group the Headhunters. The vocals are so smooth and effortlessly delivered by the Product G&B. All the elements work remarkably well together but what really kills it is Santana’s guitar playing. It transforms the track into something timeless. Its distinctive sound was sampled for the 2017 song “Wild Thoughts”.
This is the story of how a catchy chorus of a power pop song still rocks to this day. You can argue it’s a little cheesy but who doesn’t like cheese? It’s fun and upbeat nature just adds to the song’s charm. Guitarist and vocalist John Hampson wrote it after an argument with his then girlfriend and later on saw her smiling while in conversation. It’s sweet and endearing. It remains the band's only hit single but we’re not complaining. It’s a good hit single to have.
This is aggressive and right from the opening riff, you’re gonna wanna break stuff. Sometimes it’s one of those days where you need to let off some steam. This is the song to channel that anger. The music video is of particular note as it contains quite the collection of cameos. In it you’ll find Snoop Dogg, Dr. Dre, Eminem and his daughter, Pauly Shore, Jonathan Davis of Korn, Riley Hawk, son of Tony Hawk, and model Lily Aldridge. Still, it’s one of the group’s best songs and remains a staple of their live show.
For her album, “Music”, Madonna took an experimental approach incorporating various styles and genres to its tracks. “Don’t Tell Me” is a good example of that as it has a country and folksy vibe to it. But it also mixes in some electronic elements that make it very catchy and very danceable. The guitar on the track has a stutter effect which gives it a futuristic feeling. There are a lot of ideas going at the same time but it all works together beautifully. Critically, it was well received upon first release with some even saying it’s one of Madonna’s best ever singles.
After massive hits with “Just a Girl” and “Don’t Speak”, “Simple Kind of Life” wonders what life would be like away from all that success. It’s a deeply raw and personal song penned by vocalist Gwen Stefani. In it she poses what if she went and started a family instead of being a part of No Doubt. Its lyrics are somber and the music reflects that tone with its lo-fi sound. Critically the song was praised for Stefani’s approach and vulnerability put on display. We’re glad she chose to continue with her musical career.
There are not many quite as soulful and distinctive as Macy Grey. Her raspy voice just plays out beautifully in what is ultimately a breakup song. It just has the right tone to convince you that there’s hope in saving a relationship but if you listen carefully to the lyrics, it’s clear that one party isn’t ready to admit that it’s over. If you’ve ever been in that situation, it’s a painful place to be and Grey is able to capture the complexity of being in such a state.
JLo was riding high when this song was released. It was the lead single off her second album, which is her highest selling. It’s not hard to see why. It’s got an addictive beat along with catchy lyrics. It also focuses on relationship dynamics where Lopez presents a woman who is not motivated by expensive material goods from their partner. It’s a strong message that pushes back against the idea that women are gold diggers. It’s definitely a standout song for Lopez as it was part of the Super Bowl Halftime Show she did along with Shakira.
Hope rings eternally in this tune from the Irish rockers. After experimenting with electronic dance music previously, the group was looking to get back to their earlier sound with critics having particular praise toward the Edge’s guitar tone. Overall, everything is just so very uplifting. The lyrics have a good balance of letting go of the past and looking towards the future. Upon listening you can’t help but feel like things aren’t so bad. So if you’re in a bad mood or feeling down, put this on and you’ll realize it is a beautiful day.
If you need an anthem to pump your fist to and just belt out the lyrics, this is the song for you. Bon Jovi is in top form with this composition. There’s a larger than life chorus and there’s even a reference to Tommy and Gina from “Livin’ on a Prayer”. It’s a song that many people can relate to because, ultimately, it allows the listener to place themselves front and center and say, “this is my life”. It’s something Jon Bon Jovi noted in the years since the song’s release saying that he didn’t think that the phrase, “it’s my life” could be “about everyone”.
Back in the late ‘90s and early 2000s, Faith Hill and several other women artists such as Shania Twain and Reba McEntire, were dominating the pop-country space. Hill’s album, “Breathe” is one of the best selling country pop albums of all time. With songs like “The Way You Love Me”, it’s not hard to see why. It’s just so fun and light hearted. Hill’s voice is just warm and uplifting, you just can’t help singing along. Anytime we hear it, it definitely brightens up our day. We love the way we love this song.
Appearing on the soundtrack for the film “Loser”, this song brings you back to your high school days and acts as a rallying cry for anyone who wasn’t with the cool group. It has a rockin’ chorus that you just can’t help but sing along with. It’s gritty but doesn’t take itself too seriously, telling a relatable story of a social outcast vying for the attention of a girl. She, unexpectedly, returns the feelings of interest revealing she is also a teenage dirt bag. You can present us with two tickets to Iron Maiden and we’d be thrilled. Better yet, make that two tickets to Wheatus.
Moby’s fifth album, “Play”, brought mainstream attention to the artist on a global scale. One of the most successful singles off the album was “Porcelain”, a slow, reflective piece about a relationship ending. With the use of a reversed strings sample and slow, hypnotic vocals, Moby creates a song that is emotional and distinctive. Incredibly, he was unhappy with the production and his vocals on the track. He didn’t want to include it on the album but was ultimately convinced to do so. Thankfully, he did include it because it’s still worth listening to.
A change of pace for a band known for their immaturity in their songs. Here things are slowed down as the song speaks about mental health and depression. The lyrics are more contemplative and reflective. The song was almost left off the album “Enema of the State”, as it was written later in the production cycle and bassist Mark Hoppus was concerned that it was too depressing. However, after playing it for the group, they were receptive to it and thought the song was really good.
Even though it deals with a dark subject matter, there’s a lot that keeps this record spinning time after time. There’s the driving guitars backed by aggressive drums topped off with lead singer Jacoby Shaddix’s cutting delivery. It successfully taps into a sense of angst and despair present in a lot of nu-metal tracks at the time. What really catches your attention is the a cappella intro and then you’re just pulled in once the music hits. There’s rawness present in the track that made it stand out back when it was first released and it still resonates to this day.
When Christina Aguilera first came on to the scene, she was pure pop. Her songs were light, up beat, fun and full of innuendo. And that’s exactly what we get here. Aguilera had more control over the direction of the single version of the song and the changes she made make the track a little bit spicier compared to the album version. In fact, it was too spicy for Radio Disney which actually banned the song from being played until a version came out with the racy parts removed. All we want is to keep listening to this song.
Even though it has a slow tempo, this song is no bore. It actually features a mix of musical genres such as EDM, trip hop, house and R&B. Critics at the time noted that it had a futuristic sound. Aaliyah's smooth vocals add a hypnotic element to the whole thing where you just can't stop listening. Her voice just glides effortlessly throughout. Overall, the song’s optimistic nature, in that it encourages a partner not to give up if things don’t work out right away. Unfortunately, Aalyilah would tragically pass away just over a year after this song’s release.
This song presents a stylistic shift for the Chili Peppers now that guitarist John Frusciante returned to the band. This is a dark and somber tune that speaks to some of the seedier elements of Hollywood. It’s remarkably different from their early albums. Don’t forget, these were the guys who would perform wearing nothing but socks over their groins. However, the song’s themes remain ever present as it speaks to the shallowness of celebrity. With the increasing influence of social media making it possible for almost anyone to achieve notoriety, the Chili Peppers definitely had their finger on the pulse.
Probably one of their more underrated songs but it hits hard with its fast paced drum and bass that form the foundation of the track. Built on top of that is a mix of styles and sounds including rap, organs and gospel but yet, somehow, it all works. According to Big Boi, Outkast was looking to do something different from what was popular at the time and they sure nailed it. Despite it not being a huge hit in terms of sales, it has received tons of critical acclaim over the years.
Ostensibly this song is about moving on but even after all this time, we still can’t get it out of our heads. Upon first release, it marked a big shift for the group. Not only was it the first single off their, at the time, upcoming album but they had also just split from their former label and manager after being defrauded financially. The result is the band waving bye, bye, bye to the past and onto new beginnings. What we’re left with is an edgier sound and a killer music video to boot.
Back when Eminem was just starting to hit his stride, this song introduced his alter ego, Slim Shady, to a wider audience. It lets the world know that Slim will attack anyone in ruthless fashion if you find yourself in his crosshairs. Aside from airing his views on the state of pop music at the time, he also showed some of his masterful and complex rhyming schemes. Incredibly, this track almost didn’t make it onto the final cut of “The Marshall Mathers LP” as it was only completed hours before the album was finalized.
The title track off of Spear’s sophomore album let you know she’s back when it was released in April 2000. Though some have called “Oops” a retread of “Baby, One More Time”, we certainly don’t have a problem with it as both are certified bangers. The difference here is that this time round Britney presents a woman who knows the game and is playing with someone’s emotions and it’s all pulled off with pop-y flare. Of course there’s the music video that features Spears in a now iconic red jumpsuit along with excellent choreography.
If upon hearing the intro to this song doesn’t get pumped to do something, you need to start listening to this song more. The beat is so infectious, it just pulls you in and DMX’s gruff vocals mesh so well with said beat that you may not even notice the threatening tone of the lyrics. But what you will notice is the chorus which is just so infectious that no matter where you are or what you’re doing, you’ll feel compelled to sing along with. It’s a call to action and still rings loud and clear all this time later.
The music video for this song introduced two new members of the group, Michelle Williams and Farrah Franklin. The thing is, it’s not their vocals you hear. There had been some behind the scenes issues with previous members, LeToya Luckett and LaTavia Roberson, who were dismissed from the group. Still, that doesn’t change the fact that Destiny’s Child hit it out of the park with this song. Of particular praise was Beyonce Knowles’ vocals, which had a rap-like flow to them at a time when that wasn’t typical. Given the relatability of its subject matter, this is one that will continue to be popular for the foreseeable future.
What’s your favourite song from 25 years ago? Let us know in the comments!
Matrix link: insert here
Freelancer Notes (optional):
Welcome to WatchMojo and today we’re counting down our picks for 25 songs we’re listening to 25 years later. For this list we’ll be including songs that were released in 1999 but were popular in 2000.
#25: “Never Let You Go” (2000)
Third Eye BlindWhile “Semi-Charmed Life” will probably always be their biggest song, “Never Let You Go” is a worthy listen. It really pulls you in, starting with its catchy guitar riff. It’s coupled wonderfully with the song’s lyrics. It builds nicely to the chorus which you can easily find yourself singing along with. It was well received by critics at the time of its release with praise for lead singer Stephan Jenkins’ vocals. The song was considered the standout track on the band’s second album, “Blue”. We definitely say we don’t want to let this song go.
#24: “What’s Your Fantasy” (2000)
Ludacris feat. ShawnnaThis is the debut single from Ludacris and what a way to burst onto the scene. He would go on to have massive success in the following years but it all started with this track. Lyrically the song is all about sexual fantasies, so we can’t get into it as it is pretty explicit. But what we can say is that Ludacris brings it with his delivery and flow, especially with the stuttered delivery of the main hook. It’s a good introduction to Southern hip hop which has a distinctive flair from traditional hip hop.
#23: “Maria Maria” (1999)
Santana feat. the Product G&BWhat you may not realize is that this song's main riff was inspired by a Wu-Tang song. It’s got a deep driving hip hop beat that makes you want to move. Its drums are sampled from the jazz fusion group the Headhunters. The vocals are so smooth and effortlessly delivered by the Product G&B. All the elements work remarkably well together but what really kills it is Santana’s guitar playing. It transforms the track into something timeless. Its distinctive sound was sampled for the 2017 song “Wild Thoughts”.
#22: “Absolutely (Story of a Girl)” (2000)
Nine DaysThis is the story of how a catchy chorus of a power pop song still rocks to this day. You can argue it’s a little cheesy but who doesn’t like cheese? It’s fun and upbeat nature just adds to the song’s charm. Guitarist and vocalist John Hampson wrote it after an argument with his then girlfriend and later on saw her smiling while in conversation. It’s sweet and endearing. It remains the band's only hit single but we’re not complaining. It’s a good hit single to have.
#21: “Break Stuff” (2000)
Limp BizkitThis is aggressive and right from the opening riff, you’re gonna wanna break stuff. Sometimes it’s one of those days where you need to let off some steam. This is the song to channel that anger. The music video is of particular note as it contains quite the collection of cameos. In it you’ll find Snoop Dogg, Dr. Dre, Eminem and his daughter, Pauly Shore, Jonathan Davis of Korn, Riley Hawk, son of Tony Hawk, and model Lily Aldridge. Still, it’s one of the group’s best songs and remains a staple of their live show.
#20: “Don’t Tell Me” (2000)
MadonnaFor her album, “Music”, Madonna took an experimental approach incorporating various styles and genres to its tracks. “Don’t Tell Me” is a good example of that as it has a country and folksy vibe to it. But it also mixes in some electronic elements that make it very catchy and very danceable. The guitar on the track has a stutter effect which gives it a futuristic feeling. There are a lot of ideas going at the same time but it all works together beautifully. Critically, it was well received upon first release with some even saying it’s one of Madonna’s best ever singles.
#19: “Simple Kind of Life” (2000)
No DoubtAfter massive hits with “Just a Girl” and “Don’t Speak”, “Simple Kind of Life” wonders what life would be like away from all that success. It’s a deeply raw and personal song penned by vocalist Gwen Stefani. In it she poses what if she went and started a family instead of being a part of No Doubt. Its lyrics are somber and the music reflects that tone with its lo-fi sound. Critically the song was praised for Stefani’s approach and vulnerability put on display. We’re glad she chose to continue with her musical career.
#18: “I Try” (1999)
Macy GreyThere are not many quite as soulful and distinctive as Macy Grey. Her raspy voice just plays out beautifully in what is ultimately a breakup song. It just has the right tone to convince you that there’s hope in saving a relationship but if you listen carefully to the lyrics, it’s clear that one party isn’t ready to admit that it’s over. If you’ve ever been in that situation, it’s a painful place to be and Grey is able to capture the complexity of being in such a state.
#17: “Love Don’t Cost a Thing” (2000)
Jennifer LopezJLo was riding high when this song was released. It was the lead single off her second album, which is her highest selling. It’s not hard to see why. It’s got an addictive beat along with catchy lyrics. It also focuses on relationship dynamics where Lopez presents a woman who is not motivated by expensive material goods from their partner. It’s a strong message that pushes back against the idea that women are gold diggers. It’s definitely a standout song for Lopez as it was part of the Super Bowl Halftime Show she did along with Shakira.
#16: “Beautiful Day” (2000)
U2Hope rings eternally in this tune from the Irish rockers. After experimenting with electronic dance music previously, the group was looking to get back to their earlier sound with critics having particular praise toward the Edge’s guitar tone. Overall, everything is just so very uplifting. The lyrics have a good balance of letting go of the past and looking towards the future. Upon listening you can’t help but feel like things aren’t so bad. So if you’re in a bad mood or feeling down, put this on and you’ll realize it is a beautiful day.
#15: “It’s My Life” (2000)
Bon JoviIf you need an anthem to pump your fist to and just belt out the lyrics, this is the song for you. Bon Jovi is in top form with this composition. There’s a larger than life chorus and there’s even a reference to Tommy and Gina from “Livin’ on a Prayer”. It’s a song that many people can relate to because, ultimately, it allows the listener to place themselves front and center and say, “this is my life”. It’s something Jon Bon Jovi noted in the years since the song’s release saying that he didn’t think that the phrase, “it’s my life” could be “about everyone”.
#14: “The Way You Love Me” (2000)
Faith HillBack in the late ‘90s and early 2000s, Faith Hill and several other women artists such as Shania Twain and Reba McEntire, were dominating the pop-country space. Hill’s album, “Breathe” is one of the best selling country pop albums of all time. With songs like “The Way You Love Me”, it’s not hard to see why. It’s just so fun and light hearted. Hill’s voice is just warm and uplifting, you just can’t help singing along. Anytime we hear it, it definitely brightens up our day. We love the way we love this song.
#13: “Teenage Dirtbag” (2000)
WheatusAppearing on the soundtrack for the film “Loser”, this song brings you back to your high school days and acts as a rallying cry for anyone who wasn’t with the cool group. It has a rockin’ chorus that you just can’t help but sing along with. It’s gritty but doesn’t take itself too seriously, telling a relatable story of a social outcast vying for the attention of a girl. She, unexpectedly, returns the feelings of interest revealing she is also a teenage dirt bag. You can present us with two tickets to Iron Maiden and we’d be thrilled. Better yet, make that two tickets to Wheatus.
#12: “Porcelain” (2000)
MobyMoby’s fifth album, “Play”, brought mainstream attention to the artist on a global scale. One of the most successful singles off the album was “Porcelain”, a slow, reflective piece about a relationship ending. With the use of a reversed strings sample and slow, hypnotic vocals, Moby creates a song that is emotional and distinctive. Incredibly, he was unhappy with the production and his vocals on the track. He didn’t want to include it on the album but was ultimately convinced to do so. Thankfully, he did include it because it’s still worth listening to.
#11: “Adam’s Song” (2000)
Blink-182A change of pace for a band known for their immaturity in their songs. Here things are slowed down as the song speaks about mental health and depression. The lyrics are more contemplative and reflective. The song was almost left off the album “Enema of the State”, as it was written later in the production cycle and bassist Mark Hoppus was concerned that it was too depressing. However, after playing it for the group, they were receptive to it and thought the song was really good.
#10: “Last Resort” (2000)
Papa RoachEven though it deals with a dark subject matter, there’s a lot that keeps this record spinning time after time. There’s the driving guitars backed by aggressive drums topped off with lead singer Jacoby Shaddix’s cutting delivery. It successfully taps into a sense of angst and despair present in a lot of nu-metal tracks at the time. What really catches your attention is the a cappella intro and then you’re just pulled in once the music hits. There’s rawness present in the track that made it stand out back when it was first released and it still resonates to this day.
#9: “Come On Over Baby (All I Want Is You)” (2000)
Christina AguileraWhen Christina Aguilera first came on to the scene, she was pure pop. Her songs were light, up beat, fun and full of innuendo. And that’s exactly what we get here. Aguilera had more control over the direction of the single version of the song and the changes she made make the track a little bit spicier compared to the album version. In fact, it was too spicy for Radio Disney which actually banned the song from being played until a version came out with the racy parts removed. All we want is to keep listening to this song.
#8: “Try Again” (2000)
AaliyahEven though it has a slow tempo, this song is no bore. It actually features a mix of musical genres such as EDM, trip hop, house and R&B. Critics at the time noted that it had a futuristic sound. Aaliyah's smooth vocals add a hypnotic element to the whole thing where you just can't stop listening. Her voice just glides effortlessly throughout. Overall, the song’s optimistic nature, in that it encourages a partner not to give up if things don’t work out right away. Unfortunately, Aalyilah would tragically pass away just over a year after this song’s release.
#7: “Californication” (2000)
Red Hot Chili PeppersThis song presents a stylistic shift for the Chili Peppers now that guitarist John Frusciante returned to the band. This is a dark and somber tune that speaks to some of the seedier elements of Hollywood. It’s remarkably different from their early albums. Don’t forget, these were the guys who would perform wearing nothing but socks over their groins. However, the song’s themes remain ever present as it speaks to the shallowness of celebrity. With the increasing influence of social media making it possible for almost anyone to achieve notoriety, the Chili Peppers definitely had their finger on the pulse.
#6: “B.O.B” (2000)
OutkastProbably one of their more underrated songs but it hits hard with its fast paced drum and bass that form the foundation of the track. Built on top of that is a mix of styles and sounds including rap, organs and gospel but yet, somehow, it all works. According to Big Boi, Outkast was looking to do something different from what was popular at the time and they sure nailed it. Despite it not being a huge hit in terms of sales, it has received tons of critical acclaim over the years.
#5: “Bye Bye Bye” (2000)
NSYNCOstensibly this song is about moving on but even after all this time, we still can’t get it out of our heads. Upon first release, it marked a big shift for the group. Not only was it the first single off their, at the time, upcoming album but they had also just split from their former label and manager after being defrauded financially. The result is the band waving bye, bye, bye to the past and onto new beginnings. What we’re left with is an edgier sound and a killer music video to boot.
#4: “The Real Slim Shady” (2000)
EminemBack when Eminem was just starting to hit his stride, this song introduced his alter ego, Slim Shady, to a wider audience. It lets the world know that Slim will attack anyone in ruthless fashion if you find yourself in his crosshairs. Aside from airing his views on the state of pop music at the time, he also showed some of his masterful and complex rhyming schemes. Incredibly, this track almost didn’t make it onto the final cut of “The Marshall Mathers LP” as it was only completed hours before the album was finalized.
#3: “Oops!... I Did It Again” (2000)
Britney SpearsThe title track off of Spear’s sophomore album let you know she’s back when it was released in April 2000. Though some have called “Oops” a retread of “Baby, One More Time”, we certainly don’t have a problem with it as both are certified bangers. The difference here is that this time round Britney presents a woman who knows the game and is playing with someone’s emotions and it’s all pulled off with pop-y flare. Of course there’s the music video that features Spears in a now iconic red jumpsuit along with excellent choreography.
#2: “Party Up (Up in Here)” (2000)
DMXIf upon hearing the intro to this song doesn’t get pumped to do something, you need to start listening to this song more. The beat is so infectious, it just pulls you in and DMX’s gruff vocals mesh so well with said beat that you may not even notice the threatening tone of the lyrics. But what you will notice is the chorus which is just so infectious that no matter where you are or what you’re doing, you’ll feel compelled to sing along with. It’s a call to action and still rings loud and clear all this time later.
#1: “Say My Name” (1999)
Destiny’s ChildThe music video for this song introduced two new members of the group, Michelle Williams and Farrah Franklin. The thing is, it’s not their vocals you hear. There had been some behind the scenes issues with previous members, LeToya Luckett and LaTavia Roberson, who were dismissed from the group. Still, that doesn’t change the fact that Destiny’s Child hit it out of the park with this song. Of particular praise was Beyonce Knowles’ vocals, which had a rap-like flow to them at a time when that wasn’t typical. Given the relatability of its subject matter, this is one that will continue to be popular for the foreseeable future.
What’s your favourite song from 25 years ago? Let us know in the comments!
