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The ESRB doesn't see the full game anyway. Developers and publishers submit videos to the ESRB showing examples of potentially rating-increasing content, someone at the ESRB watches the video, and they decide on a rating, tags, and, if the game is a major enough release, a paragraph on the ESRB website about the most important things to know before buying the game.
For something like a Leisure Suit Larry game, there's so much the ESRB needs to know that either they'll fail to find everything or, more likely, the video is missing something.
An example is Rain City, that point-and-click game released a month ago. One of the ESRB tags concerns drugs and alcohol use (tobacco included, for the record). Early in the game--early enough that it's in the demo--you see a bunch of NPCs smoking and drinking beer in an apartment room appropriated into a bar. The player character even buys a pack of cigarettes from a vending machine to give to an NPC who really wants something to smoke. The ESRB didn't have this tag for Rain City because, most likely, the publisher didn't include that for the ESRB to see.