In order to say both "happy New Year" and "happy birthday Scotty", here's a picture saved by Non Stop - clipped from a very early copy of Sidewalk - that didn't readily fit into any of the loose themes of previous posts.
I'd date it at around 1995-96 - and its an ad for the 1990s home-grown skate company STM, based within Rollersnakes, which produced boards, clothes and, more importantly, a zine ('The System') and a VHS video magazine ('VideoLog) in the mid 1990s. I say "importantly" with reference to the contributions both the zine and video mag made to UK skate history, as 'The System' provided early jumping points for Sidewalk dons Andy Horsley (as photographer/editor/writer) and Ben Powell (who I clearly remember being pictured in one issue, ollieing over one of the benches in Broadmarsh bus station).
Anyway, all of the Rollersnakes/STM output of the time was in keeping with the now well-established tradition of royally ripping the piss out of beloved co-conspirators, American skateboard heroes, and cross-over attempting corporate giants alike.
This STM ad combines all three elements. Dope photo of bonafide street urchin with a long-expired nickname (does anyone still call Scotty 'smudge'?); a piss-take of American pro-shoe ads (with features including "toe venting system, infused with the power of the dark one.... authentic dog shit smell"); and a photo of wrecked pair of Reebok's abortive attempt to copy Airwalks with 'Scotty' written on them in tippex.
Scott rips on a skateboard, and has far smarter trainers these days.
My first ever skateboard was a Rollersnakes complete with an STM deck (maroon, with a simple Dark Side of the Moon-style pyramid line drawn motif), purchased in the summer of 1996 during a weekend visit to Nottingham, after watching Rob Johnson fly over a full-sized road cone in Market Square. I decided it was the dopest thing I'd ever seen, and I had to at least give it a try.
On the subject of dope things, check this photo of Gaz Jenkins from Sidewalk in the early 2000s conquering the National Watersports Centre steps. Happy New Year.