To answer the question though, I believe the first person to don the heavy energy drink branding was Sandro Dias, rocking the Red Bull helmet and water bottle for the on-the-deck shots. I have no clue what he would've been making but I'd imagine it was some pretty good coin, there were a lot of televised vert events. I'd imagine he's a pretty cool person if you were to reach out to him with questions on social media.
he was rocking it as early as 2003 -
that is at least the oldest clip i could find
this is around the time i first remember red bull even really getting popular. We didnt get it in Canada til a little bit later
I thought Sheckler might have been one of the first to wear the actual New Era Fitted hat, but the earliest clip i could find of him repping the bull was 2009!! i really cant remember who the early riders were. Maybe he was the one to start that lame ass trend though!
i feel like it really took off once sheckler was on
nyjah rebrand was 2012 and thats when the monster hat came into effect. Him, Lutzka, and Pudwill were already wearing the kooky hats ~2007 (this was the tail end of the tall T era). Chris Joslin came on the scene shortly after I feel like and cemented in the hat
Thanks for your insight on this Salman
thats cool we have someone who was around the contest scene to give us the history!!!