Big Brother 50

Big Brother Issue #50 (July 1999) celebrates the magazine's fiftieth issue with a retrospective looking back at the first four years of one of skateboarding's most controversial publications. Alongside its anniversary feature, the issue delivers a strong mix of skateboarding interviews, contest coverage and the deliberately offbeat humour that had become the magazine's trademark.

The centrepiece is The History of Big Brother, a "best of" retrospective revisiting the magazine's most memorable stories, pranks and controversies from its first fifty issues. Skateboarding features include interviews with Adam McNatt, discussing his career and outspoken views on skateboarding, photographer Rick Kosick, offering a rare look behind the lens at one of the most influential figures documenting the era, and Swedish skateboarder Mathias Ringström. The issue also covers the 1999 Big Brother Awards, the Tampa Pro Contest, plus regular departments including News, Skatepark Reviews, Skate Flicks, Goddamn Ams, Product Reviews, Video Game Reviews, CD Reviews and Last Call.

Outside skateboarding, the magazine continues its eclectic editorial approach with interviews featuring hip hop producer Prince Paul and electronic duo The Chemical Brothers, alongside reports from the bizarre Glissexpo trade show, an introduction to neighbouring publication Hot Boat, and Dave Carnie's satirical 12-Step Program. Equal parts anniversary celebration and snapshot of late 1990s skate culture, Issue #50 captures Big Brother at the peak of its influence, balancing genuine skate journalism with the provocative humour and cultural detours that set it apart from every other skateboard magazine of its era.