220px-mrhankeyschrismasclassicscoverTrey Parker – “Merry Fucking Christmas” – (1999)

Probably one of the most offensive Christmas songs of all time, but then again it is from an album called “Mr. Hankey’s Christmas Classics.” I’ll admit, I don’t watch South Park and haven’t seen an episode in a long time, but I have seen the Mr. Hankey episode. You might not like it, but this song is actually very funny.

220px-the_phantom_menace_ostJohn Williams & the London Symphony Orchestra and the London Voices – “Duel of the Fates” – (1999)

“Duel of the Fates” is a seriously epic piece of orchestral music. With the choir, it has a very “O Fortuna”-feel to it. Originally featured in Star Wars:Episode 1 – The Phantom Menace, the piece has been a recurring piece of music throughout every successive piece of Star Wars film. It’s great – and, it actually appeared on TRL for 11 days. 

Mariah Carey feat. Joe & 98 Degrees – “Thank God I Found You” – (1999)

This song is from Mariah Carey’s “Whisper Period” – those years in the late 1990s/early 2000s where she barely made any noise on any of her songs and it just sounds like she’s humming words in the next room. Fortunately, this track features boy band 98 Degrees and late-90s R&B dude Joe to provide actual lyrics. Because it is a Mariah Carey song technically from the 90s, it obviously went to #1. But it’s by no means the best of them.

Gloria Estefan & ‘N Sync – “Music of My Heart” – (1999)

There are two big names behind this song. No, not Gloria Estefan and ‘N Sync – but Diane Warren and David Foster. If you don’t know who they are, look them up as their hit-writing/producing ability is pretty strong. This song was nominated for two Grammys and an Oscar. It was a #2 hit on the Hot 100 and as I’ve had a 90s music listening resurgence lately (this includes a lot of ‘N Sync on my car radio) – I must say, this song is pretty good. Although Joey Fatone’s super red hair in the video really isn’t.

Eric Benet & Faith Evans – “Georgy Porgy” – (1999)

Cover songs have their place – sometimes they are a terrible idea and sometimes they make a good case for themselves. This is an really chill version of Toto’s 1978 hit (I hate myself for saying “chill” but I don’t know how else to put it). The very talented Eric Benet teamed with Faith Evans to cover this in 1999. It only made it to #55 in the U.S. – but it was a #2 hit in New Zealand.

Aaron Lewis & Fred Durst – “Outside” – (2000)

Fred Durst was a big deal in 1999 and 2000. Limp Bizkit was huge and they did this little (okay it was huge) tour called “The Family Values Tour” with Korn, Orgy, Primus, Ja Rule, Method Man & Redman, DMX, Filter, The Crystal Method, and a little known band called Staind. That was the 1999 lineup and it was huge. “Outside” (which would later become a hit for Staind – a band led by Aaron Lewis and promoted and produced by Durst) was first performed live and acoustically in Biloxi, Mississippi in 1999 by Aaron Lewis featuring backing vocals by Durst. Some of the lyrics were made up on the spot. Radio stations started playing the acoustic version and it ended up at #56 on the Hot 100 in 2001. Later that year, Staind released Break the Cycle – which was a monumental album (in popularity). This song, for me, marked a transition from the bubblegum pop of 1999/2000 and the more rock-oriented days of 2001 and on.

Britney Spears – “From the Bottom of My Broken Heart” – (1999)

Ah Britney in the good ol’ innocent days. This was the last single from Britney’s debut album in 1999 and it peaked at #14 on the Hot 100. It had some TRL airplay but nothing compared to the three singles that preceded it nor the one that would follow it – which just shows that the TRL audience didn’t care for the emotional ballad-type songs put out by artists who were supposed to make us happy.

#84 – The Bloodhound Gang – “The Bad Touch” – (2000)

Okay, so this album (and single) was released in Europe in 1999 but it didn’t reach American shores until 2000, thus its inclusion on this countdown. And what can you say about it? The chorus: “You and me baby ain’t nothing but mammals, so let’s do it like they do it on the Discovery channel” is fairly famous and hilarious – especially for a pop song that would end up charting at #1 in a handful of countries. It received sizeable airplay in the U.S. (and still gets some). The lyrics are fantastic – I’ve never heard so many double entendres compacted in such a short span. I really don’t know what else to say: electronic beat and almost-rap vocals. Only in 1999/2000 would this song have been a hit. It was a different time.

#17 – Garbage – “The World is Not Enough” – (1999)

Garbage was an awesome band in the 1990s. Shirley Manson has one of the best female voices in rock and roll, but this song is not their best – but it’s still decent. Okay, I feel like in every one of these Bond Song posts, I’ve just dumped on why they aren’t good. I don’t dislike them all, but if I’m counting down the Top 25 – and there are only 25 songs to choose from. Then some of them are not going to be reviewed positively. And I can’t promise when this trend will change. But there are some good ones, and while this isn’t #1, it isn’t terrible.

#11 – Incubus – “Drive” – (1999)

When I went to check my list to write this post, I thought I had made a mistake. I could’ve sworn this song was in the top 25 of our Top 200 Songs of the 90s countdown. But it wasn’t – so in that regard, I had made a mistake (I think it was actually left off that list because, although Make Yourself was released in 1999, “Drive” wasn’t released as a single until 2000). Either way, this song is amazing. This was a top ten on the Hot 100 and Mainstream Rock chart as well as a #1 on the Modern Rock chart. I like songs from Incubus from before this album, and after. But nothing they’ve done matches this, as far as I’m concerned. It’s mellow and not overly heavy but I think that is to its advantage. “Would you choose water over wine? Hold the wheel and drive.” These wonderfully delivered lyrics by Brandon Boyd really help make the song and give it the relaxed vibe that it has.

#13 – Rage Against the Machine – “Guerrilla Radio” – (1999)

Grammy Award-winning “Guerrilla Radio” was the first of three big singles from The Battle of Los Angeles. Rage Against the Machine was a pretty political band and I’m sure there is some fine meaning behind this, but I don’t care enough to figure it out. Rage only released one album after this, but this was their final album of original songs and this was the best of them.

#15 – Limp Bizkit – “Break Stuff” – (1999)

Limp Bizkit was huge at the end of the 1990s. I don’t remember hearing their music much on the radio (not this album, anyway) and especially not this song, which is packed full of profanity. Censoring music isn’t something I enjoy (I loathe it). I can see why people want to do it – all in the name of “protecting” the youth. Whatever, this is a song that you must listen to uncensored. It’s so angry and it was the ultimate pump-you-up song to listen to before sports games. It still works, too. Fred Durst just yelling about having a bad day is a great thing. You can totally relate and on days like that, this is the perfect song to listen to. You couldn’t find bigger rock stars in 1999 than Limp Bizkit and this remains my favorite song of theirs. The music video has a bunch of cameos from people popular in the day, like Seth Green and Pauly Shore.

#23 – Buckcherry – “Lit Up” – (1999)

Buckcherry used to be a badass hard rock band before they released the song “Sorry” in 2007, which ruined them forever in my mind (it was way overplayed on Top 40 radio). “Lit Up” was their first single and it received a fair amount of airplay back in 1999 – on rock stations. Gotta love a song whose primary lyrics include “I love the cocaine, I love the cocaine.” If you say “Buckcherry,” this is the song I think of. Rightfully so.

#32 – Blink-182 – “What’s My Age Again?” – (1999)

This is, hands down, my favorite Blink-182 song. It’s upbeat and definitely more pop-punk than straight punk (which I prefer). This was the first single from Blink that really showed you where they were headed and what they were going to do. There are lyrics in the jokes – well the album title is a great joke in itself (Enema of the State). It’s about growing up but acting like a kid – which is pretty much what Blink-182 was all about. Or at least they were back when this was a regular on TRL. Another great song from 1999.

#38 – Supergrass – “Pumping On Your Stereo” – (1999)

Supergrass was a British alternative rock band and this was their biggest charting single – in that it charted on the most charts, although not in the U.S. I do, however, distinctly remember seeing the crazy music video on MTV and MTV2 back when it was released. It’s a pretty kick-ass song. I’m not sure what it means, unless “pumping” is some kind of weird British slang meaning “rocking.” But I’m no linguist. Oh, and Happy Leap Year!

#41 – Crazy Town – “Butterfly” – (1999)

Hey, man, what the hell – this song hit #1 in 2001. Yeah, yeah. But this album was released in 1999. You could say that this song totally doesn’t belong here but whatever I’m calling it a “grey area” and leaving it here. I do remember it more for its post-2000 radio play, but at the same time, in my mind, the 90s continued on up until September 11, 2001. That’s when the fun of the 90s kind of ended. And this was a #1 in March of 2001… within the year and a half of leftover 90s that were 2000 and 2001. Crazy Town popped up near the end of the popularity of rap rock or nu metal – genres more or less owned in those days by Limp Bizkit – but Fred Durst never had a #1 hit.

#46 – Korn – “Falling Away From Me” – (1999)

Korn’s Issues was released near the end of 1999 and this was the album’s first single. It’s awesome. So is the music video. This was the follow-up single to “Freak on a Leash” which has one of the best music videos of all time and this one, while not nearly as cool, is still pretty good and I distinctly remember it owning TRL for a little bit – the mark of any successful song from 1999. Actually, the video was directed by Fred Durst of Limp Bizkit. This song came out during a time when TRL (the then-current barometer for music popularity) featured songs from bubblegum Britney Spears backed up against alternative metal songs like this. It was an interesting (and awesome) time to be a music fan. Korn rocks.

Britney Spears – “Sometimes” – (1999)

This was Britney’s second single and while it was nowhere near as successful as the title track from …Baby One More Time, it almost cracked the top 20 in the U.S., peaking at #21. The music video was a TRL mainstay for the duration of its eligibility – and let’s be honest, Billboard’s inconsistent and screwy chart rules in the mid and late-90s made it so TRL was almost a more recognizable form of song popularity. The video features really lame choreography because Britney was nursing a wounded knee during its shoot. It’s basically Britney in white showing that she was “pure” – in contrast to the “Baby One More Time” video which was kind of the opposite. This song might be kind of annoying today but back in 1999 it was just another pop hit.

Kenny G – “Auld Lang Syne (Millennium Mix)” – (1999)

Why is Kenny G always barefoot on his album covers? Put some shoes on, it’s weird. Bizarrely, this album charted in the top five on the Hot R&B/Hip-Hop Albums chart. This version of the song was a top ten hit in the U.S. at the end of 1999. It features sound clips – a walk through the history of the 20th century. It made everybody nostalgic, and since everyone thought the world was about to end, I guess that was a good thing. The song is less about Kenny G, really, and more about the sound clips which are pretty interesting. It’s like a first-hand version of “We Didn’t Start the Fire.” Plus, “Auld Lang Syne” is the New Year’s song for whatever reason (it’s got something to do with Scotland).

Fiorello & the Guy Barker International Quintet feat. Jude Law & Matt Damon – “Tu Vuo’ Fa L’Americano” – (1999)

This song was originally written in 1956 by, guess who, Renato Carosone. This is my favorite version of it. It featured Jude Law and Matt Damon singing from the movie The Talented Mr. Ripley (which is an awesome movie). This song was – in a way – very popular during 2010. Yolanda Be Cool & DCUP used it in their hugely popular “We No Speak Americano.” When I think “Italian songs,” I immediately think of “Tu Vuo’ Fa L’Americano.”

Energpisy – “Joselito” – (1999)

“Joselito” is an instrumental flamenco song. Flamenco music originated in Spain in the 18th century and today has become famous for featuring amazing guitar work. And adding Flamenco + Spain = Flamenco dancers, which I expected to see everywhere (which was a dumb thing to expect). I did see one in Park Guell in Barcelona. This is the kind of music you hear in your mind walking around Spain – or the kind of music you hear on some kind of travel documentary while a camera man is walking around Spain.

#15 – Prince – “1999” – (1982)

If you wanna hear this on YouTube, be quick – Prince is notorious for not allowing anyone to hear and song he is even associated with unless they are throwing all kinds of money at him. Not only is this one of the best songs of the 80s, it’s one of the best songs of the 90’s as well – having re-charted and received a lot of airplay in its title year. It was this party anthem that put Prince on the map. The follow up single, “Little Red Corvette” made it into the Top 10 and after that, “1999” made it to #12. In 1999 it re-charted at #40, making it Prince’s last Top 40 hit. I think this has to be Prince’s defining song. “Purple Rain” gets a lot of attention, but that was because of the accompanying movie. If “1999” was a movie, then this would surely get more attention.

#1 – Santana feat. Rob Thomas – “Smooth” – (1999)

Here it is, number one. This song was, well, massive, and I didn’t care for it much at the time (as it was overplayed). But man, oh man, how I love it now. It was the last #1 single of the 1990s and of the 20th Century. It spent 12 weeks at the top but it considered the most popular #1 single of all time (if you take into account total sales and time spent on the chart). It won 3 Grammys and Billboard ranked it #2 on their list of all-time #1 singles (behind “The Twist”). Oh, and it’s completely kick-ass. Chorus: “And just like the ocean under the moon / Well that’s the same emotion that I get from you / You got the kind of lovin’ that can be so smooth / Gimme your heart make it real / or else forget about it.” Not only are the lyrics delivered with severe punch from Mr. Thomas but ol’ Carlos on the guitar really tears it up. This song provided a real comeback boost for Santana, as they’ve had multiple hits since (and this was their biggest hit since 1971). The other from Supernatural was “Maria Maria” (also a #1 hit featuring The Product G&B). Other awesome lyrics: “Man it’s a hot one / like seven inches from the midday sun / I hear you whisper and the words melt everyone / but you stay so cool / my muñequita, my Spanish Harlem Mona Lisa / you’re my reason for reason / the step in my groove.” This song was an excellent way to end the 90s and really the only way to end this countdown. After 6 months and 200 tracks it’s finally over, but we’ll be back in a few months with another countdown (but don’t expect it to be 200 songs).

#7 – Ricky Martin – “Livin’ La Vida Loca” – (1999)

This song kicked off the Latin music boom of 1999. I remember where I was when I first heard this song and I knew right away it was going to be huge. It is catchy in a way that most songs can only hope to be. It hit #1 on the Hot 100. Everyone thought they could speak Spanish when they became able to roughly translate “la vida loca” into “the crazy life.” Congratulations multi-lingual population. Ricky had some other hits in the 90s before moving into the 00s. Also from his self-titled album was “She’s All I Ever Had.” “The Cup of Life,” from a year earlier, was named the official song of the 1998 FIFA World Cup. Some lyrics: “She’ll make you take your clothes off and go dancing in the rain. She’ll make you live her crazy life but she’ll take away your pain. Like a bullet to your brain, come on!” And the chorus: “Upside inside out, she’s livin’ la vida loca. She’ll push and pull you down, livin’ la vida loca. Her lips are devil red, and her skin’s the color mocha. She will wear you out, livin’ la vida loca.”

#25 – Third Eye Blind – “Never Let You Go” – (1999)

This is my favorite Third Eye Blind song – no it isn’t as good as “Jumper” and nowhere near the level of “Semi-Charmed Life” – but the way in which it is sung is very catchy. Blue was released in 1999, after the band’s popularity had peaked but it still managed another hit single: the slower “Deep Inside of You.”