3. Pokemon Rival/Gary Oak (Pokemon)
We suppose this entry could go for all rivals in the Pokemon series, but none of the recent ones outdo the original. In Pokemon Red/Blue you begin your Poke journey watching the privileged grandson of a researcher take a starter with a type that counters your own. As you continue your quest he keeps showing up when you're at your most tired and weak, snidely bragging about his skills. He even bests the Elite Four and the Pokemon Champion before you! Sure you ultimately defeat him, but man, what a dick.
Your rival's pushy, blow-hard nature was taken to new extremes as Gary Oak displayed in the original run of Pokemon anime episodes. He had a personal squad of cheerleaders, virtually never lost, and rode to gym battles in a fancy car, all while taunting Ash at his slow progress. It took Ash 270 episodes to finally beat him, which was well past the point most people were watching the show. Today the internet has come to embrace him as the coolest guy that ever lived, but we'll never forget how he treated us on his way to the top.