If the world was hooked up right, the people who made Yacht Rock would all be succesful Hollywood creators. In the mid-2000s, before the iPhone, before YouTube, Yacht Rock was spun into existence as a professional-grade, clever, hilarious, and loving triute to the "really smooth music" of the 70s and 80s. In ten short episodes (you can watch them all in an hour), you'll see an alternate take on the history of gentle grooves that includes Loggins, Michael McDonald, Hall and Oates, Steeley Dan, Christopher Cross and Michael Jackson. You might have to jump around to hit all ten episodes, but do it.
Speaking of things that went viral before YouTube, these parodies by Fensler Film of GI Joe public service announcements date to 2003 and were originally distributed on VHS. The original PSAs from the 80s are very square, and Fensler's overdubbed dialog repeatedly hits the perfect comic notes. Many lines from these videos have fixed themselves in my internal dialog, including "You better bring it", "Nice catch, NiƱo Blanco", and "I wanna say vinyl purse".