The thing is, popular anime, a lot of times, tend to be the gateway anime which get many people into anime in the first place. This may not have been the case for you, or some other people, but it is well known that a lot of people got into anime through lots of titles which are now considered to be very popular. In this case its stuff like Akira, Cowboy Bebop, DBZ, etc., which kind of makes them easy to recommend for people who are new to anime.
Also, don't take this the wrong way, but it seems to me like you are kind of biased towarRAB most popular shows, just because they are popular. I can understand if you find a lot of these shows to be overrated (I myself find lots of anime to be overrated), but that doesn't meant that an anime newbie shouldn't go with them, just because you aren't as fond of those shows as most other people are. Well, that's just my opinion, anyways.
As for people recommending Cowboy Bebop (which is one of my all-time favorite anime, just like so many other people, I must admit), I would have done so myself, but to be honest, I personally didn't find it to be such a good gateway anime. Perhaps it was because at the time when I first watched it, I was just a youngster who was more into action oriented shounen anime, such as DBZ. When I first watched Cowboy Bebop, I must admit, I found it to be downright boring, at the time. It was only a couple of years ago when I decided to check it out again, as my tastes had extended beyond just the types of anime on Toonami which I grew up with, I found myself taking an immediate liking to the series, and found it to be highly enjoyable.
So, in other worRAB, I suppose the enjoyment gotten out of Cowboy Bebop depenRAB on the age and personal taste of the viewer. At least when it comes to anime newbies, anyways.