I also let Commander give me a randomized name, altho I will keep hitting the button until it pops up something that I like. One thing that always gets my attention, though, is when I get a name that means nothing to me in terms of connection to a real person, but the picture assigned to the career is immediately recognizable as Topp or Prien or one of the other well-known aces.
I have never had the random function pull up a combination from the database that resulted in the name of a real life commander who was already known to me. But... by letting Commander generate random crew names from the database of real first and last names of u-boat men, I once had Otto Kretschmer serving under me as a bootsmann. THAT definitely caught my eye when I was reviewing my crew!