I guess Simon won. He's turned a bunch of amateur talent contest shows into mega hits, he has a good eye for spotting crappy music that teen girls love, he bangs lots of hot women, owns a yacht, and when he wants a baby, he just knocks up his buddy's wife because he thinks she'll make a good mom. I guess he's missing shit like humility and dignity and decency and a bunch of other stuff that no guy can really be expected to care about when he's banging hot women on his yacht. If life were Monopoly, Simon would own Boardwalk and Park Place, all the Utilities, and be forcing Rich Uncle Pennybags to blow him behind the Reading Railroad station. Fuck that smile.
Photo Credit: WENN [gallery ids="1520972,1520982,1520992,1521002,1521012,1521022,1521032,1521042,1521052"]