Transworld 2008 25th Anniversary Issue

Transworld Skateboarding – 25th Anniversary Issue

This special edition marks 25 years of Transworld Skateboarding with a dense, nostalgic, and celebratory look back at the culture, personalities, and moments that shaped skateboarding since the mag’s first issue dropped in 1983. It opens with a nod to the very first subscriber and quickly dives into highlights both quirky and iconic: Top Fives, “Must Haves,” and a revisiting of Back in the Day with none other than Spike Jonze.

There’s a heavy emphasis on evolution—in skate style, magazine format, and media itself. “Beyond the Pages” takes you into Transworld's foray into video, a move that helped define modern skate media. “Look Forward to the Past” reverently revisits earthshaking tricks like Mike McGill’s McTwist and Heath Kirchart’s El Toro lipslide—each still too gnarly to wrap your head around.

The mag also puts the spotlight on its inner circle, giving love to both pro skaters and the editorial team that shaped TWS’s voice. “Pro Staffed” acknowledges how many legends walked through its offices, while “Judging It by the Cover” dissects the most iconic and controversial TWS covers ever made.

A few standout sections reflect on rivalry and legacy—like “Transworld vs. Thrasher,” framed as a battle of “Skate & Create” vs. “Skate & Destroy.” The issue even pokes fun at itself while owning its influence, joking about being called the “Bible of skateboarding” before cheekily suggesting, “Let’s call them the Koran.”

Wrapping things up, Check Outs gives belated nods to guys like Koston, Penny, and MJ, and Last Words closes on a strong note with Andrew Reynolds—the Boss himself—symbolizing the future of style and drive in skating.

A sincere, self-aware, and packed issue—this one’s part time capsule, part love letter to skateboarding’s ever-evolving universe.