During a photo session inside of Merlot's studio, Merlot announces that her team of models have been accepted to host a line of perfume, with Sherry as the spokes model. To celebrate, Merlot decides to throw a party on her yacht the Coral Clipper in Miami. Sherry is about to get on board the yacht when a cigarette boat called the LookSea slammed into it to avoid a manatee. The yacht begins to sink and everyone on board, including Sherry, dies. However, Sherry realizes this was all a dream and has just seen a terrible premonition on the brink of happening. Sherry creates a fit and manages to drag her boyfriend, a few other models, and a photographer named Gunter Nonhoff off the yacht before it sets sail. She also desperately tried to get Merlot off the ship but she stayed on, even after much protest. While the gang waits at Pier 13, they see the yacht crash and sink, just like Sherry predicted. As the ship is sinking, a piece of debris comes flying over and maims Sherry's face beyond recognition. Sherry goes into a coma for a month, her only contact being Cabernet herself; her boyfriend had dumped her and started to date Rose, one of the survivors. After awaking from the coma and staying in the hospital for three months, she is released and goes back to her apartment, where her friend throw her a "Welcome Home" party. During the party, Gunter gives Sherry a mask of what she used to look like, which only disgusts how her friends treat her. She screams for all of them to leave and horrible with how she looks, Sherry later attempts to commit suicide via hanging. Before she can, the chair she's standing on breaks and she receives a phone call from Death to meet her at a café. As she arrives, she finds Death posing as an elderly African American man with gray hair and a gray suit on. He gives Sherry an ultimatum to grant her face back as long as she assists him in killing her so-called "friends." Sherry agrees and begins to go around causing the deaths of every survivor in the story or preventing their aid during their time of peril, most notably when she did nothing to save Chablis from having her face eaten away by chemicals, Chardonnay when she was drowning in her hottub, or stopping Rose from having liposuction with outdated mahcinery, which sucked out all of her organs. As each survivor dies, her face is slowly reconstructed by Death.
It wasn't until Sherry met with Gunter after Cabernet went into labor that her secret was slowly being revealed. While talking about Death and all of the mysterious accidents, Sherry accidentally shouted out that it was Chablis, Shiraz, Chardonnay, Rose, and Brut's time to go. However, Gunter was unaware of Brut's death and just as he puts the pieces together, he is severed in half by a truck. Sherry watches the photographer die right in front of her and more of her face is repaired. With only one survivor left, Sherry goes over to Cabernet's room after Death forces her to watch her die. But as she's watching her in labor, she suddenly remembers that Cabernet was the only person who bothered to visit her while she was in a coma, crying and pleading for her to wake up. Sherry runs out of the room into a bathroom, crying and talking to a disembodied form of Death in the mirror. Sherry breaks her deal with Death, saying she won't watch how Cabernet die, and smashes the mirror before collapsing to the floor.
Cabernet eventually had the baby and lived, but Sherry was admitted into a Psych ward for the breakdown and shouting out she cheated Death, where the only visitor was Cabernet herself. While recovering, Cabernet learned of a facial reconstruction program and Sherry went into the program, where her face was fully prepared.
Sherry is the last survivor of the Coral Clipper accident to die.
Getting ready to spend some time with Cabernet, Sherry leaves her apartment and sees her sitting in her limo with her son. While crossing the street to get in the car, her cellphone rings. Sherry stops running and looks down and realizes the person calling her reads, "DEATH". Sherry looks back up and sees a bus driven by Death himself that appeared out of nowhere coming right at her.
- In Sherry's vision of the yacht sinking Sherry died when she drowned due to the pressure of the sinking vessel dragging her underwater as she tried to swim back to the pier.
- Sherry died out of order; she was supposed to have died after Cabernet, but Sherry intervened and let her live. Had Sherry observed Cabernet during childbirth, she would've died, but Sherry broke her deal with Death after realizing her only friend is Cabernet.
- Sherry's death occurs a year after the Coral Clipper accident.
- The destination sign on the bus reads TERMINAL.