A Look at Skateboarding’s Most Iconic Covers

Before the rise of social media and the internet, how did people who were obsessed with skateboarding learn about the newest names, tricks, and boards? Two ways — they watched skate videos, and they read skate magazines.

The history of skate magazines is filled with massive names, but nothing in the world of skating was more influential — particularly in the 1980s and 1990s — than the covers. Landing a cover image on one of the top skate mags was basically the highlight of a skater’s career, way before the arrival of the X Games or skateboarding’s spot in the summer Olympics.

Here are some of the most incredible skate mags in history and a few of their killer covers.

Meet Thrasher

If you’ve skated, you’ve heard of Thrasher Magazine. Considered by most (people with brains) to be the most influential skateboarding magazine in history, Thrasher magazine was founded in 1981 and is still going strong both in print and online.


Thrasher Magazine represented everything skateboarding was in its early days—rebellious, counterculture, and unfocused on what the establishment thought was ‘cool’ or acceptable. It was focused on the skaters, and landing a Thrasher cover or Skater of the Year award was the absolute top of the mountain for pro skateboarders everywhere.

Thrasher still commands a huge following, but it’s hard to overstate just how significant it was in its heyday through the 80s and 90s.

Transworld Strikes Back

Two years after Thrasher came onto the scene, a rival stepped into the ring. Transworld Skateboarding, or TWS, was everything Thrasher wasn’t — and that was the point. The Transworld founders thought that skateboarding’s popularity meant that the world deserved a less harsh, more ‘accessible’ magazine that kids could enjoy.

While this might seem like the most uncool, least-skateboarding-like move of all time, Transworld actually turned out to be a respected mag—even if it never got quite the same iconic status as Thrasher.

Transworld built a big following and ultimately lasted until 2019 before shutting down production. Before that, it helped launch the careers of many a skating pro and inspired generations of riders to pick up a board.

Big Brother is Watching

A decade after the founding of Thrasher and Transworld, a new challenger showed up. Founded by Steve Rocco in 1992, Big Brother was the unofficial-official magazine of street skating. As the 90s saw street skaters become the biggest names in the sport, Big Brother took advantage of that changing culture and gave them a magazine that focused on their interests—and a whole lot more.

Big Brother loved controversy from the beginning, its founders getting high off the act of pushing as many buttons they could. Along articles and photos relating to skateboarding was content about how to create fake IDs, scam people, and even commit suicide.

Photo credit: Ginko Press

Still, Big Brother managed to hold on for over 20 years, finally closing down shop in 2004. Many believe that the magazines’ interest in stunts, pranks, and all-around craziness led to the rise of the massive show Jackass and its stars, with many of the show’s creators pointing to the magazine as inspiration.

Will a new skate magazine rise to take the place of these classics? What does a ‘modern’ skate mag look like in the digital world? Only time will tell, but in the meantime, we have these classic mags to look back on and remember the way things were.