While not a "funny joke", there's a nice in-joke on one of the radio stations (I can't remember which it is right now), there's a girl speaking that's scared crazy of all modern technology, and a caller calls in talking about a super computer and identifying himself as "Emmanuel from Long Island" (I could be "Eric from Long Island" as well), the interesting part is that it is the actual voice of Eric Corley, a.k.a Emmanuel Goldstein (he really is from Long Island), a well known computer hacker, radio talkshow host (he had a great call-in show in the late 80's now available online) and founder of the 2600 magazine.
I saw on his credits that he also appeared in GTA III, though I can't remember hearing him there.
Being a fan of his radio shows, and recently having listened through all his "Brain Damage" shows (aired 1988-1995) I reacted instantly to hearing his voice on that vice city radio station.
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