In this special Halloween episode, Kelly is joined by the ultimate Crime Junkie, Ashley Flowers, to chat about all things true crime and the weird and spooky. Ashley and Kelly talk about the Menendez trial, OJ Simpson, and their shared obsession with Court TV. The Deck Investigates host gives her honest opinion on the Karen Read trial, the supernatural mystery of the crying boy paintings, and Kelly shares a ghost story of her own!

Kelly is joined by everybody's teen crush, actor and producer Rob Lowe. He gives updates on the St. Elmo's Fire sequel, which of the original actors are set to return, if he's in contact with Judd Nelson, and whether or not he had a crush on Demi Moore. Rob shares his thoughts on the infamous NY Magazine Article that birthed the term "The Brat Pack" and gives his honest opinion on Andrew McCarthy's documentary BRATS. Kelly gets intel on his friendship with Oprah and Rob shares his favorite Lorne Michaels quotes and how his wife Sheryl locked him down.

The hilarious Chelsea Handler joins Kelly to explain her process and practice as a self proclaimed "farm to table gynecologist", and her special talent of dosing out street drugs. The two Jersey girls bond over their similarities and love of therapy. Chelsea shares what it was like growing up as the youngest of six in a house with no rules and talks about her upcoming Little Big Bitch Tour.