A number of heroic, lovable rogues and bad-ass outright villains have appeared throughout this list. Harry Flashman is neither of these. He's a liar, a scoundrel, a coward, and a fraud. Through the course of twelve books, he squirms into and out of a host of sticky situations, usually through blind luck and obsequious charm. He likes to drink, to seduce women, and to stay alive. He's sort of a James Bond without the courage or skill. (Coincidentally, or perhaps not, Flashman author George MacDonald Fraser also penned the screenplay for seminal Bond film Octopussy).
Fraser yanked Flashman from the pages of Thomas Hughes' classic Victorian text Tom Brown's Schooldays, wherein Flashman was a fiendish bully (think Kirk's Finnegan from Star Trek's Shore Leave episode). Fraser conceived of an entire backstory for this two-dimensional blackguard, granting him a hedonistic, slippery personality and using his ejection from Rugby as the launching pad for an epic narrative of unintentional martial adventure and ungentlemanly conduct. An example: the first thing young Flashman does upon his expulsion from school is to attempt to rape his father's mistress in the family home. Right away you know you're dealing with a morally vacuous creature. And from there the character stays true to form, owing as much to Hefner as Kipling, copulating and dissembling his way across the British Empire and beyond. He's not sympathetic or likable, and yet he's utterly human and somehow it all works. Despite every ounce of your modern sensibilities raging against the chauvinism and racism and dishonesty and selfishness of the bastard, you root for him anyway.