Richard Hilfiger (Son of Tommy Hilfiger)

Richard Hilfiger is the son of the famous fashion designer, Tommy Hilfiger. Richard didn’t pursue a career in fashion like his father, but rather made a name for himself in alternative rap music going by the name, Rich Hill. He was also reportedly dating Rita Ora for a good year before they split up in 2015. He apparently didn’t inherit good qualities either, being arrested after his breakup for possession of illegal drugs and involved in a club fight more than once. Being a kid of a celebrity sure isn’t easy!

Marston Hefner (Son of Hugh Hefner)

Hugh Hefner is one of the biggest names in the Hollywood industry and best known for his Playboy mansion and his Playboy bunny girlfriends. Hugh Hefner has a son named Marston. Hefner Junior gave his father headaches after making headlines all over the world as he was charged with domestic violence against one of Hefner’s bunnies, Claire Sinclair. Fortunately, his sentence was to join a domestic violence program for one year. On top of that, Marston has gotten a bachelor’s in philosophy and has apparently written a book about zombies that’s called Bleed.