GAIL DAUGHTRY and the Celebrity Sex Pass

The film opens in a small Kansas town. A mailman named Frank (Fred Melamed) narrates about the people in the town, saying that he likes everyone, but his personal favorite is Gail Daughtry (Zoey Deutch).

Gail is a hairdresser who works with her best friend Otto (Miles Gutierrez-Riley) and has never left her hometown. She is engaged to Tom (Michael Cassidy), her high school sweetheart.

Gail and Tom are in line at the book store for a celebrity signing. After having a discussion with Otto, Gail asks Tom who his “celebrity sex pass” is (a celebrity that they would sleep with if given the consent from their partner). He claims it’s Tilda Swinton, and Gail says hers is Jon Hamm. They enter the store, where Jennifer Aniston is reading from her recipe book. After Gail and Tom meet her, Tom pretends that he left his jacket inside. After over an hour, Gail goes back into the store to find Tom having sex with Jen, as he told her it would help them through their relationship, though Jen realizes that’s not the case at all and tries apologizing to Gail.

Gail later joins Otto on a trip to California to see a celebrity stylist, Remy Fontaine (Thomas Lennon). At the airport, two guys – Sergio (Joe Lo Truglio) and Marco (Matthew Jason Cwern) – get excited when they see Henry Winkler. Gail takes pictures for them, inadvertently mixing up their suitcases.

Sergio and Marco get into a limo with their boss, a criminal named Ludovica (Sabrina Impacciatore). She opens their case and sees Gail’s belongings, so she kills Marco for taking his hands off the case. Ludovica orders Sergio and his new partner Niccolo (Mather Zickel) to track Gail down, find the real case, and kill her. They start by trying to track a selfie Gail and Otto took in front of Grauman’s Chinese Theater.

Gail and Otto visit a psychic named Charlotte (Kerri Kenney-Silver), who knows what Gail has gone through and why is is troubling her. Charlotte gives Gail her solution: in order to save her relationship with Tom, she must use HER celebrity sex pass and sleep with Jon Hamm.

The two friends start by asking a map salesman (Michael Ian Black) for directions to find Hamm’s house, but he points them out to the Creative Artists Agency. There, they meet a young aspiring agent named Caleb (Ben Wang), who tries to help by talking big to his boss…which gets him fired. However, he managed to swipe Hamm’s home address off a desk at work.

Gail, Otto, and Caleb arrive at a mansion, which turns out to be owned by Weird Al Yankovic. He bought the house from Hamm a long time ago, and Al prepares to defend his property by shooting at the trio. They make their escape and run into a paparazzo named Vincent (Ken Marino). He was a hotshot photographer for People Magazine, but getting a pic of Hamm has been his “great white whale” since he never got his shot and has been disgraced ever since. Vincent joins the trio in search of Hamm.

Vincent uses his connections to track down the address of Hamm’s former “Mad Men” co-star John Slattery, who has not had a lot of work in recent years. He tries to keep the group away with self-defense, but Caleb gets him in the balls first. Slattery is not too keen on helping them, but Caleb delivers a speech to convince him to join them. Slattery looks through a bunch of unanswered texts from Hamm to get a lead.

The group arrives at Hamm’s new location at the Chateau Marmont. They meet his security guard Terrence (Tobie Windham), who refuses to let them in. Gail explains her whole situation to Terrence, who takes pity on her. He comes back out after a moment of speaking to Hamm, who says he will meet with them if they bring him a pitch for a movie that he can star in.

The group leaves to work on their idea, with Vincent being the writer, Caleb pitching it to Hamm, and Slattery being set to star in it. When Gail opens her briefcase, she sees that she has the wrong one. Inside are a bunch of classified documents and government papers. They use it as the basis for their film.

Everyone starts to head back to the hotel when they are found by Sergio and Niccolo, just as the hairstyling convention with Remy is starting. Niccolo tries to shoot Gail, but Otto steps in the way. A metal plate in his head causes the bullet to bounce back towards Niccolo’s skull, killing him. Remy also burns Sergio with curling irons to the face since he and Niccolo back their truck into him.

Ludovica and Sergio end up taking Gail and Otto hostage, and then order Slattery, Caleb, and Vincent to bring her the briefcase or they’ll die. They arrive at an abandoned film set, where Ludovica gets what she wants but still orders her men to kill the group. Slattery then unleashes his self-defense moves to kill all the henchmen, ending with him kicking Sergio’s face clean off. Ludovica tries to escape, but each member of the group takes a shot at punching her in the face, even as Gail tries to be reasonable with her. The adrenaline in her takes over, and Gail just beats Ludovica to a dead bloody pulp.

The group returns to Hamm’s hotel room, where they meet the man face-to-face and pitch their film to him. Although he thinks it’s a good idea, he chooses to pass on it. Gail steps forward and admits her whole mission to sleep with him and how she was helped by her best friend and new friends. Touched by this, Hamm helps the group with certain things, like getting Vincent his photograph, getting Caleb his job back, and Slattery getting a new movie role. Gail and Hamm end up having crazy sex that she enjoys.

Gail and Otto return to Kansas in time for Gail’s wedding. However, after the adventure she’s had, Gail says she cannot marry Tom since there is so much of the world she wants to see. Hamm them shows up in a hot air balloon and whisks Gail away to parts unknown, agreeing to keep things casual.

Frank ends the story, saying he doesn’t know what happened to Gail because she literally just left, and he starts ranting to the audience about why people don’t give a shit about him.