1990s novel about a man trapped in simulated historic New York

Question

I read this in the late 1990s and I think it was fairly contemporary then. Some things I recall:

• The protagonist is part of the company that makes virtual reality simulations.
• Somehow he gets trapped in a simulation of a historic American city (fairly sure it is New York).
• At one point he is gaoled in a prison ship, where he befriends a Rastafarian.

Answer 1

I'm not quite sure but it sounds like Simulacron-3 (1964), a.k.a Counterfeit World, by Daniel F. Galouye.

Simulacron 3 is the story of a virtual city (total environment simulator) for marketing research, developed by a scientist to reduce the need for opinion polls. The computer-generated city simulation is so well-programmed, that, although the inhabitants have their own consciousness, they are unaware, except for one, that they are only electronic impulses in a computer.

The simulator's lead scientist, Hannon Fuller, dies mysteriously, and a co-worker, Morton Lynch, vanishes. The protagonist, Douglas Hall, is with Lynch when he vanishes, and Hall subsequently struggles to suppress his inchoate madness. As time and events unwind, he progressively grasps that his own world is probably not "real" and might be only a computer-generated simulation.