23. Scott Disick
The notorious man-child who can always be counted on to produce a litany of toolish comments has been up to a lot this year. He tried to open a restaurant but, as expected, failed after the place had been open for slightly over six months. We're not surprised because Scott having a job wouldn't make sense: he's too good at spending money to make it.
He also continued to be a douchey "partner" to Kourtney Kardashian as he was spotted all over a blonde woman while Kourtney watched the kids. Finally, he dropped $15K to impress Yeezy. We're sure they will make great brothers-in-law.