Howard is not witty (except when being fed lines). As an interviewer he constantly interrupts and steps on his guests funny lines. He isn't very intelligent or at least he is incredibly uninterested in learning about politics, history, music, sports, etc. About the only real talent I have seen in the guy is that he lies flawlessly and he and his agent are masters at self promotion.
Here are some others without talent who have made it "big" (not counting realty tv people) in entertainment or broadcasting without deserving it in my opinion:
Adam Sandler, Queen Latifah, Keanu Reeves, Larry King, Ben Stiller, Chris Berman, Tim McCarver, Barbara Walters, Dick Clark, Rick Dees, Jimmie "JJ" Walker, David Brenner, Greta Van Sustern, Andrea Mitchell, David Bowie, Brittney Spears, Jackie Mason, Rachel Maddow, Glenn Beck, Adam Durwitz (or whatever the name is for that horribly off key, pretentious singer for the Counting Crows), Dan Rather, and Robin Quivers (although it's stretching it to say she made it big, she is without any talent and is very well known).
Anyone else you can think of who made the big time with as little talent as Howard?