9. Larry Laffer (Leisure Suit Larry Series)
Job: Getting Laid/Love Seeker
Poor Larry: hes just a guy looking for love in all the wrong places. Hes a generally unfunny dork who, after living for an extended time in his parents basement, sets out to try and score with every hot lass he comes across. Larry, being Larry, is pretty terrible at the whole thing, enough so that the series has spawned five sequels (with two off-shoots starring his lame descendant), all of which are charming and fun in their own weird and formulaic way. He often finds 'love' in each game, but a running joke of the series is that his paramour leaves him in wacky fashion so that he must set out on the next adventure to pursue romance with another lovely lady. So unfortunate is Larry that he and Captain Thygh, the one woman* he might have a lasting romantic connection with, are beamed up into a UFO mid-coitus. *There are two games in the middle of the series where Larry has a girlfriend named Passionate Patti, but she's written out of the series by the time Leisure Suit Larry 6 happens.