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About This Time 20 Years Ago…

It’s The Hits Of September-ish 2005!

September 7, 2025
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The Hottest Hit On The Planet…

"Album cover for Kanye West's 'Gold Digger' featuring Jamie Foxx."

It’s “Gold Digger”
by Kayne West

He seemed so nice at first. Being nice “for a rapper” was pretty much his defining feature.

And when I say “nice”, what I guess I really mean is, “middle-class.” Respectable.

"Close-up of a man wearing sunglasses against a colorful background, featured in The Guardian in 2017."

The kind of rapper The Guardian might like to interview.

The rapper whose first paid job was not as a drug dealer. This felt important. It made him stand out.

Kanye was the rapper who liked his mother: Donda.

Kanye was the rapper whose mother was an English professor, Chair of The English Department At Chicago State University.

"Smiling woman holding a baby, showcasing a joyful moment of connection."

Kanye was the rapper who spent a year in China when he was 10, because his mother was on an exchange there,  and there aren’t many rappers who feature details like that in their origin story. Later on, Kanye’s mother would become his manager. This felt important. It made him stand out.

Kanye may not have spoken particularly clearly early on, but that wasn’t because he had bullet fragments in his tongue like 50 Cent. It was because the doctors had to wire his jaw shut after he’d been in a car crash.

Kanye West in hospital after a serious car accident, highlighting a pivotal moment in his life.

And sure, that crash was largely Ye’s fault because he’d fallen asleep at the wheel, but that’s just because he was working so hard.

But more importantly, he survived because he wasn’t too cool for a safety belt. Kanye West was the rapper who rapped about the importance of safety belts. This felt important. It made him stand out.

Kanye was the rapper who dressed like a college student, complete with backpack.

"Portrait of a man in a red jacket with a Louis Vuitton backpack, posing confidently."

Sure, it was a Louis Vuitton backpack, and it likely contained not a single book – what with Kanye being a proud non-reader of books and all –

But it still felt important. It made him stand out.

Kanye was the rapper whose first three album titles:

  • College Dropout
  • Late Registration
  • and Graduation

…were seemingly chosen to appeal to his college student target demographic. That made him stand out.

In a rap world that was split between the thug-gangsta rap of 50 Cent on one side:

"50 Cent's album cover for 'Get Rich or Die Tryin'' featuring a muscular man with a shattered glass effect."

…Which sold gargantuan numbers of copies,

…and the socially conscious rap of Common on the other:

(Which sold considerably less…)

Album cover for "Like Water for Chocolate" by Common, featuring a vintage black and white photo with a green border.

Kanye rose up through the middle with a little bit of everything.

Of course, a lot of people hated Kanye from the start.

Hating Kanye, amongst certain corners of the Internet, was as guaranteed a like-magnet as hating Nickelback. Hating Kanye was easy. You didn’t even have to listen to his music.

All you had to say was “I’mma gonna let you finish”, or “I’m a proud non-reader of books”, or “WE THE ROCKSTARS!!!!”

Kanye West performing live with a microphone, wearing sunglasses and a black shirt.

In fact it was probably easier not to listen to the music, because then you’d have to admit that the music undermined your entire joke. Because the music was frequently brilliant.

I mean, sure, Kayne’s tendency to put his foot in his mouth during interviews was only matched by his tendency to put his foot in his mouth during his recorded works.

Screenshot of a Tinder chat featuring humorous messages about using Kanye West quotes for dating.

Rare is the Kanye track that doesn’t feature a line so corny you can’t help but conclude he put it in there on purpose to make sure you were paying attention.

If being the nice, respectable rapper was Kanye’s most distinctive feature early on, it was soon overtaken by another: his conviction that everything he said and did was of historical significance.

This is a guy who started the video for “Diamonds From Sierra Leone” – the single before “Gold Digger:”

Quote by Kanye West about Sierra Leone and diamonds.

–  with an historical quote from that fearless leader… himself!

The fact that Kanye was struggling with these issues – between the lure of bling and its real-world costs – felt like a big deal. Or at least it would have if the original version of “Diamonds From Sierra Leone” had actually dealt with the issue outside of the song title. If he then didn’t proceed to rap about… stuff like this:

 “If your stripper name “Porsche” and you get tips from many men
Then your fat friend, her nickname is “Minivan””.

That feels a little bit off-topic, Ye.

Kanye had apparently already written his verses before Q-Tip tipped him off about blood diamonds and how they were funding a civil war, sending Ye down a rabbit hole. It’s not always a good idea to send Kanye down a rabbit hole, but this time it turned out kind of nice (“Diamonds From Sierra Leone” is a 10.)

“Diamonds From Sierra Leone” may be the most typical Kanye track: Obsessed with bling, but self-consciously so.

Early on his career, it was the ethics of bling-obsession that was his favourite topic. “Gold Digger” fits this theme; a discussion of the economic realities of dating a gold digger – you can win the Superbowl and still drive off in a Hyundai – whilst providing sage advice to prospective gold diggers to consider their investments from a long term perspective; look for the guy with ambition in his eyes, this week he’s mopping floors, next week it’s the fries… with the punch line at the end that, for all your efforts, you may still be traded in for the inferred ultimate in blingy accessories: a white girl.

"Musician performing on stage in green attire with a band, featuring a vibrant set design."

It had been about two years since Outkast had dropped “Hey Ya:”

Somebody needed to come along and fill that “rap stars that white people like” shaped-hole. And “Gold Digger” is roughly as joyous a track as “Hey Ya”.

If Andre 3000 could create a party classic about getting divorced, Kanye could make one about how when she leaves your ass, she gonna leave with half… unless of course you ain’t no punk, and holler “WE WANT PRE-NUP YEAH!” (that line pretty much filling the “ICE COLD!!” shaped hole of audience participation.)

And yet for all of this, the main reason “Gold Digger” instantly became the biggest hit Kanye had yet grabbed:

– arguably the biggest hit that Kanye would ever grab – was doubtlessly due to the Ray Charles sample. Or more specifically:

Most Jamie Foxx… doing a Ray Charles impersonation… over the top of a Ray Charles sample.

"Collage of Jamie Foxx portraying Ray Charles in various performances."

Jamie Foxx’s performance in Ray the year before was still enormously popular. For many people, “Gold Digger” may as well have been a movie soundtrack hit. For many people, those Ray/Jamie bits of “Gold Digger” are the only parts they like.

I feel sorry for those people.

"Stylish duo posing against a vibrant pink background."

“Gold Digger” is a comedy routine in which virtually every line is a punchline.

It’s a comedian routine that at least tries to empathize with both sides; the economic realities that governs both the gold digger and her mark. That’s a lot for a pop song to carry and still be catchy. But “Gold Digger” succeeded. And in doing so, it made Kanye feel important.

It stood out.

“Gold Digger” is a 9.


Meanwhile, in Mash-Up Land…

Alt text: "Album cover for 'Doctor Pressure' by Mylo vs Miami Sound Machine."

It’s “Dr Pressure”
by Mylo

Mylo was a clever lad.

Almost certainly the most famous dance-producer/pop star to come out of the quaint and chilly village of Portee on the Isle Of Skye, Scotland.

Before he decided to become a dance producer/pop star however, he went to Oxford to study Psychology, Philosophy and Physiology…

Before heading off to Los Angeles to study even more Philosophy.

Young man sitting casually against a wall, wearing a green sweatshirt and jeans.

Turns out that there isn’t actually a good buck in that racket, so he went back to Scotland to try and be the new Daft Punk or something.

None of that is immediately apparent on “Dr Pressure.”

Or in fact, anything else that Mylo recorded, most of which was clever, but in that dumb, “anybody could do that… but why didn’t I think of it?” kind of way.

I guess it takes a certain genius to mash-up “Bette Davis Eyes” and “Waiting For A Star To Fall”?  

Now, the Isle Of Skye was exactly known for its dance scene – a DJ did move to Skye in the late 90s, but Mylo had already moved out – so Mylo had mostly grown up on cheesy 80s soft rock, the only music the local station Atlantic 252 would play. It makes perfect sense that “Bette Davis Eyes” and “Waiting For A Star To Fall” would be the first songs that Mylo would think of when he turned to making dance hits.

In sampling the latter, Mylo was being weirdly prescient.

For “Waiting For A Star To Fall” had a weird little revival in 2005, with two different dance-covers of the song reaching the UK Top 5.

Alt text: "Official Singles Chart entry for 'Waiting for a Star to Fall' by Boy Meets Girl, peaked at number 9, November 26, 1988."

I mean, sure. It’s a cute song, I’ve always liked it.

But that’s crazy.

Of course, everybody was doing that sort of mash-up thing at the time.

Mylo got the basic idea from LMC’s “Take Me To The Clouds Above” which had mashed up Whitney Houston’s “How Will I Know” with U2’s “With Or Without You”. And despite the fact that it was not actually Whitney – they rerecorded it with a house diva of moderate renown – it still managed to become a UK #1.

This sort of stuff was clearly in the air.

It definitely takes a certain twisted genius to decide to sample “Invocation for Judgement Against and Destruction of Rock Music” by the Church Universal and Triumphant.

Man standing in front of a church tower on a clear day.

Not a band, but a religious organization – a pretty major one, with 30,000 adherents….

…Who would later become famous for predicting the end of the world by way of nuclear apocalypse in 1990, much to the disappointment of their followers when it never happened – that Mylo found on a compilation album:

"Cover art for 'The Sounds of American Doomsday Cults' featuring a lighthouse and coastal buildings."

The compilation was called Sounds Of American Doomsday Cults Volume 14 despite the likely non-existence of volumes one through to 13.

It was released by a label called Faithways International, whose only other release was by Aum Shinrikyo, the Tokyo sarin gas attack organisation.

Anyway, that’s my favourite Mylo track.

Even if most of the thrill is from actually hearing all these 80s acts – mostly iconic, some largely forgotten – one after another, and particularly the enjoyment obtained from hearing them mispronounce Cyndi Lauper (“Cyndi… Looper?”) (“Destroy Rock’n’Roll” is a 9.)

Given that so much of Mylo’s work is made up of costly samples, it’s lucky for him that his biggest hit – “Drop The Pressure” – sampled:

Himself.

DJ performing live with electronic equipment in a vibrant atmosphere.

Just singing into the microphone: “Motherf%@ker’s gonna drop the pressure.”

He sang that motherf&@ker was going to drop the pressure, then he motherf&@ker than he was, did indeed drop the pressure, going all Daft Punk on it’s ass.

“Motherf%@ker’s gonna, f%@ker’s gonna
F%@ker’s gonna, f%@ker’s gonna
F%@ker’s gonna, f%@ker’s gonna
F%@ker’s gonna, f%@ker’s gonna
F%@k, f%@k, f%@k, f%@k”

(sorry, Link.)

Naturally, teenage boys loved it. And those who are teenage boys at heart.

I for one am appalled to discover that it doesn’t appear to be available in the karaoke format.

KaraFun search results for "Drop The Pressure" by Mylo, currently unavailable.

Maybe it was the swearing that the critics dug.

For compared to virtually any other Top 40-centric dance producer – and make no mistake, Mylo was definitely aiming for the Top 40 – the critics absolutely loved Mylo. Pitchfork gave the Destroy Rock’n’Roll album an 8.4. That’s 1% off Best New Music! Armand Van Helden must’ve been pissed.

And it takes a certain twisted genius to take that and combine it with Miami Sound Machine’s “Dr Beat.” But Mylo himself was not that twisted genius.

Credit for “Doctor Pressure” must go to two guys called Phil’n’Dog, who’d already had some success with another mash-up, of the Muppet Show theme with, um, Electric Six’s “Gay Bar.” I’m not sure that I’d go as far as calling it “good” exactly, but… it got them played on alternative station XFM, specifically “The Remix” show.

Phil’n’Dog seemed to spend a lot of time mashing up silly songs together. They also called themselves Radio Earwax, an obvious riff on Radio Soulwax, possibly the most popular mash-up makers of all.

Nothing else Phil’n’Dog did was as popular as “Doctor Pressure.” Or even as popular as “Gay Muppet Bar.” But there was a huge appetite for mashups: MP3 blogs like Boomselection and nightclubs like Bastard, who played nothing but.

You could smash any two random songs together and feel pretty sure that some DJ somewhere would play it in their set.

Medical personnel attending to a patient on a stretcher in a clinical setting.

Now, as you will notice from the “Drop The Pressure” video, Mylo spends a lot of his time in a hospital, after falling off his motorcycle.

Presumedly it was this that made them think of “Dr Beat”, and the “emergency… paging Dr Beat” intro.

Incredibly, it worked, not a given in the world of mashups. Phil’n’Dog were constantly coming up with ideas for songs to mash together. Sometimes they’d spend entire days working on these ideas, only to find that all of their ideas were bad.

“Doctor Pressure” was not one of those bad ideas.

Miami Sound Machine’s 1984 hit “Dr. Beat” came after their initial Miami wedding band phase, and before they descended into gloopy wedding ballads.

A time when they realized that what the world really wanted was a cheesy tune filled with ambulance sirens, and a video featuring a suicidal Gloria Estefan and a crazy mad-scientist doctor in a stupid hat… and by “the world” I mean “Europe,” who liked that sort of thing. But it was too cheesy for Reagan’s America.

“Doctor Pressure” was instantly huge, and not just amongst the party-people at Bastard.

It got so big that Mylo rerecorded it himself, and it was an official proper record.

CD cover for Mylo's "Drop the Pressure" featuring bold text on a black background.

This was a rarity in the world of mashups. Most records were unofficial, and kind of illegal, because, y’know, copyright.

But “Doctor Pressure” was a proper record. And a proper hit.

Mylo could not possibly have made much money out of all his work. For “In My Arms” for example, he appears to have made none, the rights holders for both “Bette Davis Eyes” and “Waiting For A Star To Fall” asking for 50% each. But I’m sure he was philosophical about it all.

“Doctor Pressure” is an 8. (“Drop The Pressure” is a 9.)

Meanwhile in Emo-Land… 

"Fall Out Boy 'Sugar, We're Goin Down' album cover featuring silhouettes of men against a teal background."

It’s “Sugar, We’re Going Down”
by Fall Out Boy

So. We’ve already covered the folk side of emo, but what about the punk side of emo?

The guys with eyeliner side of emo. The side of emo that combined the immaturity of post-Blink 182 punk-pop, with the plot of their favourite teen-coming-of-age movie. And no emo-punk band was bigger that Fall Out Boy, a band from pretty much the same north Chicago suburbs as John Hughes movies, from Shermer, Illinois, if Shermer, Illinois actually existed.

This feels relevant. Fall Out Boy songs featured a lot of movie references.

They had one song called “Of All the Gin Joints in All the World.” A lot of teenage coming-of-age movie references. They had one song called “Nobody Puts Baby In The Corner.” They had another called “A Little Less Sixteen Candles, A Little More ‘Touch Me’”, although the video makes it look as though the song was written as an excuse to make a vampire movie.

Another thing you might notice from “A Little Less Sixteen Candles…” is just because you have an excellent song title – and Fall Out Boy, in classic emo-band style, always had excellent song titles – it doesn’t mean that the words in that song title needs feature in the lyrics at all!

Fortunately, in the case of their first big hit, “Sugar, We’re Going Down”, the lyrics did. The lyrics also featured yet another movie reference.

But before we get into that, just who was Fall Out Boy?

"Close-up portrait of a man with dark hair and eyeliner against a blue background."

Pete Wentz – distantly related to Colin Powell apparently–  was by some distance the most famous member of Fall Out Boy even though he wasn’t the singer.

Instead of being the singer, Pete was the one who wrote the lyrics. He was the one who frequently freaked out and had anxiety attacks; at one point in 2005 attempting to commit suicide after an overdose of his anxiety medication. His obsession with the Boxing Day tsunami a few months earlier also appears to have something to do with it.

Most importantly, Pete had the most emo hair.

Not just in the band, but quite possibly in the whole of America.

"Smiling young man with red and black hair, wearing a white shirt and red jacket."

Pete was already pretty famous as the moody, verbose poet and ultimate emo-pin-up boy, but he’d become famouser still a year or so later when he started dating Ashlee Simpson. Later on, he’d marry her. Still later on, they’d get divorced.

That Pete might one day marry a minivan pop princess probably seemed unlikely a couple of years earlier, when he was playing in a bunch of hardcore bands.

"Black and white image of a lively punk rock concert with fans passionately singing and playing bass."

Including one called Racetraitor, famous for calling their audience “crackers”, and singing, seemingly exclusively, about racial politics.

Pete would later study Political Science. Pete Wentz is far more serious than you might expect from a punk-popper with stupid hair married to Ashlee Simpson.

So serious, that, in 2005 – the same year as “Sugar, We’re Going Down” hit – Pete also dropped a novel.

Okay, maybe that’s overstating it. It was an illustrated novel. It was named after a Smiths song:

The Boy With A Thorn In His Side. It was about the nightmares he had as a kid.

Alt text: "Cover of 'The Boy with the Thorn in His Side' by Peter Wentz, illustrated by Joe Tesauro."

So, the Pete Wentz C.V. includes:

  • lyricist
  • bass-player
  • published author

… but not the lead singer of Fall Out Boy.  

That job went to Patrick Stump.

Compared to Pete Wentz – compared to anyone really, compared to me, compared to you – Patrick Stump did not look much like an emo-punk star.

Man in vintage attire smiling while holding a classic telephone.

Or a rock star of any description.

He looked as though he’d just walked out of a Charles Dickens novel. I’m certain that whenever he meets someone he calls them “guv’nor.”

When Pete and Patrick first met, Pete thought Patrick looked like Marcie from Peanuts.

Which cannot possibly be a compliment.

"Cartoon character with short black hair and round glasses, wearing an orange shirt and black shorts."

I have a theory that it was Patrick’s glasses that inspired the Fall Out Boy moniker.

According to Fall Out Boy-lore, they were announcing their new band name one night at a show – some pretentious, arty name that they thought was clever, and was apparently also extremely long, as long as their song titles – and some drunk dude in the crowd yelled out “screw that, you’re Fall Out Boy”… and so they would become.

It’s likely the dude just meant that Patrick Stump looked like Milhouse:

"Animated character Milhouse from The Simpsons dressed as a superhero."

Who, you will remember, if you are a Simpsons nut, got the role of Fall Out Boy in the Radioactive Man live-action film.

Patrick Stump just looked like any cartoon character with glasses. Even in a post-Weezer world, Patrick was always going to get second billing.

The typical Fall Out Boy band photo features Pete out the front, whilst Patrick is in the background.

Sometimes far in the background. He’s just one of the out of focus guys, a reference I’m sure the members of Fall Out Boy would appreciate.

"Two images of a rock band featuring male members, showcasing different styles and settings."

Sometimes Patrick wears glasses. Sometimes he doesn’t. But he always wears a stupid f*cking hat.

"Four musicians posing together, showcasing diverse styles and expressions."

“Sugar, We’re Going Down” was a big chart hit, the chorus featuring one line that followers of big chart hits could appreciate: “I’ll be your Number One With A Bullet”.

Although not as obvious a movie reference as “Nobody Puts Baby In The Corner”, that line is almost certainly a reference to the bit in High Fidelity:

Where Rob (John Cusack), is compiling his Top Five Breakups List. Rob doesn’t want his most recent ex-, Laura, to make the list, just to spite her – although she isn’t aware of the list, because it’s just his own inner monologue.

"Scene from a movie featuring a young man saying 'Number five with a bullet. Welcome.'"

But when she does make the list she’s… well she doesn’t come in at Number One, she sneaks in, at “number five… with a bullet.”  

Emo bands were big fans of High Fidelity: the year before Taking Back Sunday released a song actually called “Number Five With A Bullet”. Clearly, in the emo-GOD!DAMN! ARMS! RACE! Fall Out Boy had to do better than that.

"High Fidelity playbill featuring a man in headphones at the Imperial Theatre."

When they made the High Fidelity Broadway musical a year later, it would also include a song called “Number Five With A Bullet.” I just listened to it. It displays no emo-influence.

So, “Sugar, We’re Going Down” is very much a this-is-going-to-be-the-biggest-breakup-of-your-life song. It’s full of Patrick singing mean things that Pete had written.

Mean things like:

“I’m just a notch in your bedpost, but you’re just a line in a song”, which is even less than the girl in “I Slept With Someone In Fall Out Boy And All I Got Was This Stupid Song Written About Me.”

An actual song that actually exists.

"Fall Out Boy album tracklist featuring 'I Slept With Someone In Fall Out Boy' and 'Champagne For My Real Friends.'"

This is not the impression you get from the video, which is all about the touching love story between a girl and a dude with deer antlers on his head. I guess nothing captures the essence of teen alienation quite like having deer antlers on your head.

That the video is a touching story is at least in keeping with the song title, which comes from a surprisingly sweet place.

The word “sugar” was chosen because Pete noticed that all of his dad’s old records featured the endearment, and he thought it was sad pop songs didn’t use “sugar” anymore. Also “honey.” Most of those old songs didn’t sound like “Sugar, We’re Going Down” though.

Most of those “honey”, “sugar” songs sounded more like this:

Were Fall Out Boy trying to write an Archies song? They certainly had a similar dedication to catchy hooks and ear-wormy melodies.

“Sugar, We’re Going Down” didn’t make it to Number One with a bullet. But they’d got closer than any other emo-punk band.

Unless you want to include Plain White T’s.

“Sugar, We’re Going Down” is an 8.


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Your friendly - if snarky - pop music historian!

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rollerboogie
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rollerboogie
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September 8, 2025 7:14 am

In the early to mid 00s, I was working at a church as an accompanist for a teen choir. Down the street was a Knights of Columbus hall where lots of local bands would play all-ages shows. Many of the kids in the choir went to those shows and one of the girls was a ticket taker at the door. They talked about the various bands that would play there, and one of them was Fall Out Boy. They mentioned their fondness for those shows in an interview after they got famous.

It’s interesting they came up today here. My daughter is learning to drive, and we went driving last night. She asked me to put on a Radiohead song on Spotify, and somehow that eventually led to Alice in Chains playing. and then other grunge followed. I never thought I would see the day when she would want to hear any of this, but she’s getting more into 90s harder stuff. I began thinking about the lack of band culture in the era she is growing up in. Kids in high school aren’t starting bands very much at all and haven’t been for quite awhile. It’s non-existent at her school. I felt kind of sad she was missing out on it, and was thinking about the days like the one mentioned above, where bands would play and kids would congregate. Not sure if those days will ever return. Even if rock and roll does make a comeback, cell phones and video games have taken over the culture so much, that getting kids to leave the house and gather in masses is not actually as easy as it sounds. I guess you never know what could happen, but right now, it’s not looking likely for near future.

Virgindog
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Virgindog
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September 8, 2025 7:24 am

Thanks for explaining why people liked Kanye. I never got the appeal. Now I do. Too bad he flaked out.

Zeusaphone
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Zeusaphone
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September 8, 2025 9:19 am

On the country side of the tracks, Lee Ann Womack is having man trouble…

https://www.youtube.com/watch?v=af-G7pN4XrU

JJ Live At Leeds
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September 8, 2025 12:50 pm

I liked early Kanye. Let me rephrase that; I liked the records, I wasn’t totally sold on the man. Turns out he was just easing us in gently to his character. Gold Digger is an 8. Kanye is a 0.

I know Fall Out Boy come in for stick but I don’t mind them. Never chosen to listen to them but they’re always a welcome listen on the radio. Super catchy tunes. Sugar We’re Going Down doesn’t quite match up to This Ain’t A Scene but its an 8 as well.

I haven’t thought about Mylo in a long time. The Destroy Rock And Roll album was all the rage with the trendsetters. Then he disappeared and we’re still waiting on the follow up. Found an article from 2016 where he said new stuff was on its way.

19 years and counting for a new album, I think he might have missed his moment.

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