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Larry Laffer, the series' main protagonist, was modeled after a salesman for Sierra Game, whom the developers hated, as he would return from sales trips and brag about how he got lucky with women.
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A Leisure Suit Larry 4 was once in production. According to Al Lowe, the game was meant to be the first multiplayer online adventure game, and was going to use a new way to play the game. However, there were many problems with the technology they had at the time, so the game was shelved. The ending to Leisure Suit Larry 3 was also very definite and had almost no way to lead to another game. Because of both of these reasons, the developers decided to skip 4 and go straight to 5 to be able to do what ever they wanted with it. The 4th game is now considered an in-joke among fans and developers.
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According to Al Lowe. There were plans for a live-action FMV Leisure Suit Larry adventure game. The only thing that came out of it was a test video shoot that everyone disliked when it was finished. Al later scrapped the game believing that Larry was more suitable for animation instead of live-action.