I used to know a guy that fit the description.
I'm not sure if he had low self esteem or what, but he always had to talk about what he had, money, women, etc. It was off putting to the point where people would basically tell him they didn't want him around. Strangely enough he kept coming back time and time again, acting the same way and expecting different results. He seemingly thought that we would eventually come around to his odd way of thinking.
He'd show up to parties or gatherings and he would just always talk about the same things over and over. If you had a story, he had a better (or often times conflicting) story. He knew everything about everything, or so he believed. He was actually pretty smart and decently educated, but for some reason had to prove himself to no end.
Sadly he could have been a decent person. He was decent looking but drove good women away with weird ego problems and ended up with sub par relationships.
He just didn't get that nobody cared about how much money he (supposedly) had, how many women he'd been with, how hot/rich they were, or anything else.
He's pretty much a burn out now, but still tries to come around.
We're all too nice to ban him from our lives, but man that guy is annoying.