Heidi Montag – $1,000,000
The former reality TV star got famous by appearing in The Hills with her boyfriend, now husband, Spencer Pratt. The couple were loved and hated far and wide, and Heidi got a ton of grief for her decisions to go under the knife. She says that she was so deeply insecure that she once had ten procedures done in one day! She regularly speaks out about her regrets about how much money she blew on her previous lifestyle, as well as her LA plastic surgery obsession.