Dent is even more clueless and out of his depth than Bilbo, though, I think.
Dent is a clueless passenger through most of the books and all he ever really wants is a nice cup of tea and foir people to stop trying to kill him, whereas Bilbo yearns for adventure and gets it.
Dent <> Bilbo
All Rincewind ever wanted was to not get involved in adventures and, needless to say, he didn't get his wish. IMHO, Rincewind is at his best in Sourcery.
In the land of the blind, the one-arm man is king.