“I was alone in the car and I said it out loud to myself, 'That guy’s pretty fly for a white guy'. And it was like, ‘ding, ding, ding!’”: Dexter Holland on how The Offspring’s silliest hit came about

The Offspring in 1999
(Image credit: Getty Images)

The Offspring had a worldwide smash on their hands with their 1998 single Pretty Fly (For A White Guy), but there might not have been a song at all if frontman Dexter Holland hadn’t fancied a Latte Macchiato from his local Starbucks (we’re presuming Holland is a Latte Macchiato kind of guy, he seems like he is). It was there whilst he was queuing to order that Holland spotted the figure who'd become inspiration for the song. Speaking to The New Cue a couple of years ago, he explained how the track came about.

“I remember driving to Starbucks one day and there was a white kid with a sideways hat,” Holland said. “Orange County is a pretty middle of the road place and he was definitely out of his element in how he was presenting himself, right? He was trying to be something he definitely wasn’t. I was alone in the car and I just said it out loud to myself, like, 'That guy’s pretty fly for a white guy'. And it was like, ‘ding, ding, ding!’, like, whoa, that’s a good line, I’ve got to remember that for something.”

At the same time, Holland continued, he’d been working on a new piece of music and realised the line would fit perfectly. “It had kind of a Latin vibe to it in a way with the chord progressions,” he said, “a little bit of a Oye Como Va vibe, it’s almost taking some of those elements and playing them in more of a punk style, taking a riff that wouldn’t normally be a punk riff and doing it with distorted guitars and seeing what you’ve got. Musically, that was the vibe.”

Holland remembers being keen to get the song out because he felt sure someone else was going to release a track that tapped into the same themes. The Offspring got there first, though. “I remember when we were recording the album in the studio,” he recounted,  “I felt like ‘someone is going to hit on this theme, I can’t believe no-one has done a song about a white guy trying to be gangster and I’m sure any day the Beastie Boys are gonna put something out, somebody’s gonna put something out, we’ve got to get this thing done’. Luckily, no-one did it before us.”

Acknowledging the song’s novelty attributes, Holland says the band’s managers were split in opinion, wondering if it was too wacky. “I remember doing some of our very first press with Australia and the lady said, “we don’t know quite what to do with the song, half of us love it and half of us hate it”,” he laughed. “I don’t know if that’s what I wanted to hear on my first interview but I just thought, ‘Well, that’s good. Half of you love it, I guess’. Maybe it was one of those kinds of songs where it was a love it or hate song and that added to its appeal. It got a reaction out of people.”

As it was, most fans fell into the former category and a new wave of listeners fell for the US punk rockers, sending Pretty Fly (For A White Guy) to the top of the UK charts. The moment Holland realised his song was connecting on a huge scale was at a show in Italy, he said. “We went to a club after and people were coming up and I was signing some things and this guy with a really thick Italian accent said, “I know a guy exactly like that guy in my school”. To me, that was the most incredible thing because I knew guys like that in Orange County and, in my head, I could see how this could translate to California or maybe the US, but the idea that a guy in Italy had the same reaction, the same feeling was like, ‘wow, this is really a global thing that I hadn’t realised.’” 

Niall Doherty

Niall Doherty is a writer and editor whose work can be found in Classic Rock, The Guardian, Music Week, FourFourTwo, on Apple Music and more. Formerly the Deputy Editor of Q magazine, he co-runs the music Substack letter The New Cue with fellow former Q colleagues Ted Kessler and Chris Catchpole. He is also Reviews Editor at Record Collector. Over the years, he's interviewed some of the world's biggest stars, including Elton John, Coldplay, Arctic Monkeys, Muse, Pearl Jam, Radiohead, Depeche Mode, Robert Plant and more. Radiohead was only for eight minutes but he still counts it.