Mike Enslin (Cusack) is a skeptic and author who debunks supernatural occurrences after the untimely death of his daughter Katie. After his latest successful book, he receives an anonymous postcard of the Dolphin Hotel in New York City bearing the message "don't enter 1408." Viewing this as a challenge, Enslin attempts to book a reservation in room 1408, but the hotel will not rent him the room. However, after being informed by Mike's agent (Shaloub) that the Fair Housing Act requires hotels to rent unoccupied rooms the Dolphin reluctantly reserves room 1408 for Enslin.

Arriving at the Dolphin, Mike is pulled aside by the hotel's manager Gerald Olin (Jackson), who warns him that no one has lasted more than an hour in 1408. Olin offers Enslin an upgrade to the penthouse suite, access to documents regarding the deaths in 1408, and an $800 bottle of cognac. Mike accepts the documents and the cognac but insists on staying in the room, frustrating Olin. The manager gives him the key, warning him that "It's an EVIL  room."