History’s Most Famous Lotharios

They wined, they dined, they were banned from entire countries for their womanizing. Meet four seducers (one present, three past) who rewrote the book of lovemaking.

Giacomo Casanova (1725-1798) was the 18th-century version of a platinum status player. The famous Venetian adventurer, writer and social icon was notorious for his prolific womanizing, and the boasting that followed hot on its heels. His weapons of choice were charm, lies, and even intimidation, which led to him being banned from certain countries (the 18th-century equivalent of girldon’tdatehim.com.) His actual “number” remains unknown, but in his autobiography, Histoire de Ma Vie, Casanova cites 122 sexual conquests.

Frank Sinatra (1915-1998) The Crooner was so much more than just the voice that made (makes?) women swoon. Ole Blue Eyes himself may have been a bit of a tramp. Despite that Italian mobster charm, he worked his bad boy appeal without getting too grimy. The secret to his seduction? An impulsive romantic streak which enabled him to sweep more than a few starlets off of their kitten-heels and into hasty marriages. Who doesn’t love a man who loves commitment?

John F. Kennedy (1917-1963) owned the Presidential Suite at Hotel Seduction. Though the slick willy of the ‘60s kept his personal life under wraps as much as possible, his torrid affairs and infamous escapades, with the likes of Marilyn Monroe, eventually leaked out. America’s 35th President was a sweet talker, and though he reportedly lacked the physical virility he exuded, the manner in which he wielded his power drew many admirers. Though, cue the collective sigh: Cheat on Jackie O., how could you?

George Clooney (1961- ) The contemporary romancer who doesn’t even have to try. His boyish good looks, crossed with smoldering bedroom eyes, give this actor an edge that allows him to seduce without even breaking a sweat. Breezing through a brief marriage years ago, this modern-day Casanova keeps it casual: no kids, no emotional baggage, and an angel-meets-imp demeanor on-screen. It’s a combo that would have any red-blooded woman yelling “Action!”