Transworld May 2001

Transworld Skateboarding – 2000 (Exact Month Unclear)

This issue of Transworld Skateboarding finds itself right at the edge of two skateboarding generations—one defined by monster ramps and larger-than-life contests, the other by gritty street skating and global exploration. The cover sets the tone with Colin McKay unleashing a kickflip into the terrifying roll-in of the Super Ramp, a move that would rattle most skaters just looking at it. McKay, always in control, turns a nightmare drop into a precision move. The mood continues with Kenny Anderson in the contents section, making clean use of Toronto’s architecture with a stylish 180 fakie pivot grind to fakie—a technical trick matched by the sleek modern backdrop.

Inside, the issue kicks off with familiar columns like Gasbag, Litterbox, Volume, and Tangent, where the magazine’s voice speaks with equal parts sarcasm, insight, and love for the culture. Any One Thing and Starting Point bring in micro-features and glimpses from around the world, while the Trick Tip helps readers level up, and Check Outs and Last Words keep the focus on the next wave and lasting impressions.

In the features section, “Toner 01” signals a fresh update in skate tech and gear coverage—new product lines and aesthetics to match the new decade. “Winging It From Coast to Coast” follows Globe’s tour across the U.S., tracking their team’s movement and chaos in equal measure. “The Good Fight” brings things back to the road as a band of nomadic skateboarders make their way to the Texas Skate Jam 2000, braving breakdowns, busted spots, and all the beautiful mess that comes with travel skating.

Brian Wenning holds down the 20 Questions segment with a raw and confident tone, offering a glimpse into the mind of one of the Northeast’s rising stars—known for his effortless style and heavy tricks. The FDR Skatepark feature captures a moment of transformation, documenting its new facelift and the way this legendary DIY space continues to evolve into a fortress of East Coast skating.

Then things take a surreal turn with “Skateboard Vampires,” a strange and theatrical trip through Europe with the DVS crew. The old-world backdrop adds a moody energy to their sessions, contrasting elegance with absurdity. The issue finishes strong with “The Seven Day War,” a wild faceoff between Cronan and Newsome, where creativity, ego, and ability collide over a week of nonstop skating.

This issue blends chaos and control, showcasing a generation unafraid to hit vert, street, or cobblestone with equal determination. From McKay’s fearless drop to Wenning’s street finesse and DVS’s vampire tour, the mag captures skateboarding at its most versatile and unpredictable.