Transworld Feb 1999

This issue of Transworld Skateboarding delivers late-‘90s heaviness with a tone of raw commitment and serious progression. The cover features Heath Kirchart in full send mode, locking into a lipslide down a twenty-stair handrail. The photo, taken by Swift, captures the sheer board bend beneath him—an image that perfectly reflects Kirchart’s reputation for skating with near-reckless control and next-level confidence. It’s more than just a trick; it’s a defining moment of calculated risk.

Inside, the contents photo doesn’t let up. Andrew Reynolds is shown mid-kickflip out of a frontside bluntslide at the Santa Barbara rails—one of those “how did he even get out of that?” moments. It’s a sequence so coveted the mag jokes about having to physically fight people off to protect it. Shot by Atiba, it radiates the explosive control and pop Reynolds was just beginning to be fully recognized for.

The columns set the rhythm: Gasbag and Litterbox deliver the magazine’s attitude and pulse, Jam Sandwich layers in offbeat cultural snippets, and Tangent dives into skate-life ephemera with wit. Starting Point brings the trip updates and snapshots of the moment, while Check Outs and Last Words give both newcomers and seasoned voices their time to shine.

The features are anchored by a major Heath Kirchart profile, diving deep into the mind and mission of one of skating’s most enigmatic and hard-hitting pros. His skating is cold and calculated, his presence larger than life—this piece captures both. Then there’s The Suitcase Life, a look into the constant movement of the skateboarding lifestyle—chronicling van rides, airport floors, and the blurred line between living and filming.

This issue is pure late-'90s Transworld: powerful visuals, no-fluff features, and a roster of skaters either cementing their legacies or pushing hard to break through. With Kirchart and Reynolds leading the charge, it reflects a moment when style and fearlessness ruled the rails—and the magazine pages.