I've never seen a movie or production of Annie where the con artists (Rooster, Lily, or Miss H) are played as actually convincing.
I have never seen a convincing production of Annie since the original, seen on tour, directed brilliantly by Mike Nichols. The biggest reason for this is that Nichols understood to play the piece for honest emotion, not push too hard. Now I mean that in musical comedy terms. Few posting here don't realize that there is no real reality when dealing in musical theater, people do not break into song the way characters do in a musical (present company, me, excepted).