No Stupid Questions

It makes people feel better about their own accomplishments while also implying they are better than others.

People should know my dick was bigger than theirs

It's a way to mask one's general insecurity by loudly stating one's boons (most likely God-given, like having rich parents or being pretty)... or a social faux pas/bad habit from someone who was just raised by silly people.

Because it's usually not a concious rational decision. People having the urge to brag may, for instance, come from a household where this was their only chance to get recognizion or attention.

“See? Dad? I was better than John. Isn't that great dad?"

Yes, John was always your favorite child. The firts born. But where is he now? Not in law school eh?

The point? We can't interact directly with reality, only with our perception of reality. People don't see what you've done unless you draw attention to it. Hard work isn't enough to succeed in social situations, you also need to persuasive present your accomplishments to those who can reward you for them.

To play devil’s advocate, strategic bragging can get you noticed by influential people who can change the trajectory of your life.

Sure, it won’t make you happy, but just look at how rich and powerful politicians leverage bragging to get their way and influence their followers.

Strong man diplomacy, while deeply flawed in the long run, can still be very effective over a single lifetime.

If you never brag at all, you’ll likely see a bunch of possibilities go to others that do, even if the brag is hollow.

"dick measuring contest." where its thier only worth., poor example, but much like with musk and bezos went in thier penis spaceships of who can do it better.

Depending on culture it can be seen as an indicator of confidence, intelligence, fun, etc.

Remember that your perception of someone is yours. Someone else can see something different. They can see a leader despite not knowing everything. They can just fully buy into what they're pitching.