Edited clip attached (~ 30 sec)
I suppose this is kinda like a football coach going for it on 4th down and 5, down by 3, with 7 minutes left in the game. If you make it and everything turns out OK, you look clever. If something goes wrong, you look like an idiot.
Clearly in this case the outcome was that - in spite of the pilot making every effort to obscure the content of his transmission - the controller understood who he was and what he was saying. The frequency was not super-congested, and it didn't sound like the controller workload was very high (from the radio traffic, anyway...)
Having said that, while I love hearing when a controller and a pilot can share a laugh, I'm not a fan of non-standard phraseology - especially when every part of one's transmission consists of it. Excusing it by saying, "it wasn't very busy, and she ended up understanding what he meant" just seems to me a little like saying "hey, this approach is like the last hundred, we can afford a little complacency, right?"
And while I haven't yet commented on the specific content of his transmission, as far as judging "how cool he sounds", I have to point out that "Double-3 Double-6 Flagship" has the same number of syllables as "Flagship Thirty-Three Sixty-Six", which was how the other voice from the cockpit ID'd as he confirmed their taxi instructions after landing, later in the archive. And "Watch out for the turb." Really? That just sounds like trying a little too hard.