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Line Rider was a memorable part of my early internet days too. I remember seeing one of those McDonald's commercials on TV and thinking it was the tightest shit. I even made a fake Pokemon card of the Line Rider (who I didn't know at the time had an actual name, Bosh), back in November '08 if the modified date is to be believed. https://puu.sh/GLlhD/b37547e714.JPG
Nice, did you ever draw your own track, record it, and then upload that video to YouTube?
I certainly drew my fair share of tracks, but sadly I never recorded them. I do have a video of a track I made in Line Rider 2 Unbound, but that's a completely different beast than the flash game, with different physics, more line types, new graphics (though I'm using the Classic graphics in the vid), and other additions/changes. Here it is if you wanna check it out anyway: https://www.youtube.com/watch?v=Je0Yg04006o
A couple more bits about Unbound you might find interesting: It's not featured in the video, but Bosh has voice acting by Tom Kenny, who I'm sure you know voices SpongeBob. Also, the game has a puzzle mode, where you're given an incomplete track, and you have to complete it to get the rider(s) to the end. The puzzle mode tracks are designed by none other than TechDawg.
This is all (very interesting) news to me; I largely stopped paying attention to Line Rider after 2008, except for watching the occasional video on YouTube. (I also enjoyed the Jack Black octagon reference you placed at the end. How many years has it been since that meme appeared on YouTube, again?)
The original video was uploaded July 18th 2008, so that'd make it 12 years. I remember when I first saw it back then, my first reaction was that it was so LAME that a COOL GUY like Jack Black was on a DUMB BABY SHOW like Sesame Street, though as you can imagine, my opinion has changed since then. :)