Kelly Osbourne is the daughter of heavy-metal musician Ozzy Osbourne and talk-show host Sharon and sister to Jack. She entered the public eye in 2002 by being her outspoken wild self on the MTV reality show about her family. She parlayed the show’s monster success into a record deal with Epic where she released Shut Up and a cover of Madonna’s “Papa Don’t Preach” and a fashion line called Stiletto Killers. Her life has been a series of ups and downs. When The Osbournes was cancelled and she was dropped from her label, she started partying hard, admittedly taking 60 Vicodin a day for a spell. She entered rehab in 2004, and again in 2005 and 2009. She wrote a cathartic 2009 memoir, Fierce, but was arrested that same year for allegedly hitting a journalist at a nightclub. She placed third on Dancing With The Stars, slimmed down and started modeling for labels like Heatherette and spent five years as a Fashion Police correspondent. Two engagements — to Luke Worral in 2011 and to vegan chef Matthew Mosshart in 2014 — were ended before the aisle. She will next be seen as a judge on Lifetime’s spinoff Project Runway Junior.