Leisure Suit Larry

Leisure Suit Larry is a series of adventure games written by Al Lowe and published by Sierra from 1987 to 2009. The main character, is Larry Laffer who, though still somewhat lovable, is a balding, dorky, double entendre-speaking, leisure suit-wearing "loser" in his 40s. The games follow him as he spends much of his life trying (usually unsuccessfully) to seduce attractive women.