Do you headcanon that Gary teased Ash not just to get under his skin but also because he's secretly insecure of living up to the expectations of being Professor Oak's grandfather? I kinda like the idea.
I mean, he has a cheerleader squad that he calls them (in the Japanese version) his girlfriends, catches (correct me on this) 40 Pokémon and badges just to flex on him. I like to imagine he's also doing this to make himself look cooler so he wouldn't look "disappointing".
Oh yeah, Gary totally was a jerk to Ash in the beggining because of the expectations weighted on him for being the "Pokemon professor's grandson" (and is also one of the reasons why I think Daisy doesn't exist at all in the anime. The way Gary acts leads me to believe all those expectation went on Gary and Gary alone).
We even see how bad he was in battles or how little he seemed to care for them during the Kanto arc, with the way he gets disqualified in the Indigo league even before Ash (both sucked BAD but the fact Gary showed much more interest in catching good pokemon hints at how perhaps battles were not the thing he likes ever since then). And the way he drops gym challenges imediately after losing to Ash in the Johto league implies a lack of attachment to that that is very contrasting to Ash, who adopts the "challenger" title as a core aspect of him by Johto's end.
And of course, the biggest proof that he totally has insecurities about the big shoes he has to fit in is the way he acts in his Chronicles episode.
He's doing something even more similar to Oak and as such, something that puts much more pressure on how good he has to be in it (also I doubt is a coincidence he is voicing those uncertainties when is just his Grandpa and Tracey around, and how he acts much more diferently when the "rival he's supposed to surpass in every level" is around).
And I don't know if I ever mentioned that, but that is a recurring theme all of Ash's most remarkable rivals have: The need to become a sucessful trainer, with a side of proving themselves worthy/better than an older male figure.
Paul's whole thing is becoming a strong trainer, much to the detriment of his relationships with both people and pokemon. All because he wants to be better than his brother.
Trip met Alder when he was a kid and that was what made Trip want to become a trainer. He focuses on being strong to be able to not only again meet Alder but surpass him.
Alain started his journey in mega evolution because of Sycamore. Once he was hired into Team Flare he had to become a strong trainer worthy of collecting keystones not only for himself but to live up to both Sycamore and Lysandre's expectations.
Even Sawyer's progress is delegated on how much he wants to become an equal to Ash.
Gladion worked to become a strong trainer both to protect his pokemon but also to generally prevent that what happened to Lillie when she was younger happens again. And with the way he uses his father's pokemon and is one of the people actively searching for him once they discover Mohn is alive, is very implied Gladion was doing all that as a "replacement" for the father they assumed was dead.
Similarly, when Gary gets his first pokemon there's a caravan of people waiting for him. Those people were most likely there because of his connection with Oak (the cheerleaders are even mentioned to be hired by his father in the novels). And after being disqualified from the Kanto League even before Ash, he becomes a much more capable trainer in Johto.
Just like all of other Ash's rivals, Gary becomes a stronger better trainer because he has to prove himself to/than a man he deems important.
And lastly Gary, like all other main rivals, is meant to be a foil for Ash, two side of the same coins. So of course Gary mirrors many of the same struggles Ash (very heavily implied in-anime and outwardly stated in-novel) has.
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