The first one is the best though and the only one I've watched religiously, especially as a hockey fan.
There's Most Vertical Primate where he skateboards and Most Xtreme Primate where he is a snowboarder.
Most Vertical Primate is funny because it co-stars Richard Kern (Al Borland from Home Improvement) as a former-skater "cool older guy" who runs a skateboard shop. There's also a Bob Burnquist cameo but I can't find a screenshot online