Leisure Suit Larry 5 expands on the multi-character feature of the previous installment, with control periodically passing between Larry and Patti. The overall difficulty is greatly reduced in comparison with past games; neither character can become trapped or die, and losing the game is impossible. Many of the items players collect on their journey are merely optional, and will not affect the game's progress.
The absence of a "Leisure Suit Larry 4" forms the basis of this newest installment, as Julius Biggs has stolen the 'missing floppies' of the game and caused Larry Laffer to become amnesiac. Larry is now in the adult film industry, working for a mob-connected company known as PornProdCorp. His boss sends him across the United States to scout for models to appear in "America's Sexiest Home Videos".
Meanwhile, Patti is recruited by the FBI to dig up incriminating evidence on two record companies which are suspected of hiding subliminal messages in their songs. At the same time, PornProdCorp schemes to eliminate the competition in their industry by donating money to CANE (Conservatives Against nearly Everything).
Al Lowe has offered several reasons for the numbering discrepancy in the Leisure Suit Larry games, ranging from a scrapped sequel to an internal office prank. In truth, a multiplayer Leisure Suit Larry game was apparently in the works, designed to be played over Sierra's burgeoning online service. The project was canceled due to hardware difficulties, inspiring Lowe to skip the "4" title entirely.
Unlike the previous games in the series, Larry cannot die, and the game cannot be brought in an unwinnable state. Al Lowe stated that he intended this game to be an interactive cartoon, therefore explaining Leisure Suit Larry 5's lack of interactivity. This led to a marked departure from the black humor seen earlier in the series.