Dr. Sexy is the main character of the fictional hospital drama Dr. Sexy, M.D. which is a guilty pleasure of Dean's. Dean denied liking the show until Gabriel sends Sam and Dean into a realm in which Dr. Sexy is "real." Gabriel is disguised as the doctor himself, which Dean points out; "The thing that makes Dr. Sexy sexy is the fact that he wears cowboy boots. Not tennis shoes."
- Season 4
- The Monster at the End of This Book (mentioned only)
- Season 5
- Season 7
- Hello, Cruel World (mentioned and voice)
- Dr. Sexy is likely based on Derek Shepherd (played by Patrick Dempsey) from Grey's Anatomy. Patrick and Jensen Ackles both starred in a short movie called Blonde, in which Patrick's character's name was Cass.