NOTE: This spoiler was submitted by Jeremy

1919 – In the Eastern European town of Schlupsk, Herschel Greenbaum (Seth Rogen) works as a ditch digger. The job is thankless and he endures harsh conditions and a number of broken shovels, but his life changes forever when he meets the love of his life, Sarah (Sarah Snook). Herschel works twice as hard to make more money, and he uses it to buy Sarah some food. She then reciprocates his feelings as the two begin to spend more time together and discuss their dreams. Sarah wants to be rich enough to buy her own family graveyard plot, while Herschel’s is to be able to drink seltzer water.

Herschel and Sarah are married, but their wedding is ruined by invading Cossacks. With all their loved ones dead, the couple move to America in the hope of a better life. Sarah becomes pregnant with their child, and Herschel gets a job at a pickle factory and only earns a nickel for every ten rats he kills. However, Herschel makes enough to buy Sarah her family plot like she wanted. One day, he is standing on a ledge when a whole pack of rats corners him. He falls backwards into a vat of pickles, which becomes sealed instantly just as the factory manager tells the workers that the factory is now condemned.

100 years later in Brooklyn, two boys play with a drone, which flies into the pickle factory. The drone bumps off the lid from the pickle vat, and the boys discover Herschel alive. He is brought before a press conference where a doctor concludes that the pickle brine kept Herschel preserved. He is overwhelmed at waking up in a new era, especially now that he learns that Sarah has been long dead. After running more tests and going through more files, the doctor tells Herschel that he has one current living relative, a great-grandson named Ben (also Seth Rogen).

Herschel meets Ben, both of them happy to know they still have living family. Ben brings Herschel back to his apartment to try and introduce him to modern technology and music. He shows Herschel that he has his own machine to create seltzer water, allowing Herschel to finally taste it. He asks Ben why there are no pictures of his family, and Ben takes out a photo album of past Greenbaums. There is a picture of Sarah, as well as her and Herschel’s son Mort. Mort had a son, David (Geoffrey Cantor), who married a woman named Susan (Carol Leifer), and they became Ben’s parents. Sadly, they died in a car accident years earlier. Herschel asks Ben what he does for work, and he says he’s a freelance app developer, and he’s been working on an app called Boop Bop for five years. The purpose of the app is to scan products and determine how ethical the company’s practices are.

Herschel asks Ben to take him to Sarah’s grave. They find that the family plot is near a bridge under a rusty billboard that drips sludge onto Sarah’s tombstone. Herschel is dismayed that she would be resting under these conditions. To make matters worse, a group of working men arrive to put up a billboard for vodka, which makes Herschel think they are Cossacks. He proceeds to fight the men, and when Ben tries to break it up, he gets punched, and the two are arrested. Ben manages to pay off their bail, but he is angry at Herschel for getting him into trouble.

Ben scores a meeting with an investor named Liam (Jorma Taccone) to potentially buy Boop Bop. However, Liam tells Ben that they cannot fund the app after his arrest, because an app that determines ethics would not look good under someone with a criminal record. Herschel proposes that they start a pickle business because “it’s a good Jewish business” and they could earn enough money to buy the billboard and tear it down, but Ben rejects the idea and Herschel himself, saying that Sarah would be ashamed to see him if she were alive. Enraged, Herschel disowns Ben and sets off to make it on his own.

Since Herschel has no money to buy cucumbers to brine, he digs some out of a dumpster, along with a bag of salt, and then uses rain water to create the brine. He gathers a cart and puts jars of pickles out. A couple, Christian (Eliot Glazer) and Kevin (Kalen Allen), come across the cart and think Herschel is selling artisanal pickles. They find it pungent and strong but they are curious to try it, and Herschel quickly starts to make money off the pickles once Christian and Kevin help get the word out. While Ben continues to try and get Boop Bop back up-and-running, he sees that Herschel’s pickles have taken off. Feeling angry, he makes a call to the health department, and a health inspector comes by to shut the stand down after it is revealed Herschel gets the cucumbers from the dumpster.

Christian and Kevin help Herschel get back on his feet by inspiring to hire interns since he wouldn’t have to pay them. He gets a bunch of interns to properly brine and package the pickles, and they quickly go back to business, all while Ben continues to struggle. Herschel secures enough money to purchase the billboard and take it down so it can no longer bother Sarah’s grave. He brings the billboard back to Ben’s apartment to proclaim his victory, but Ben just wants him to go away. After Herschel says something insensitive, Ben then suggests to Herschel that he create a Twitter account to get the word out about his business.

Herschel goes ahead and makes a Twitter account and has his intern Clara (Molly Evensen) look over his posts. They are extremely offensive to women, the disabled, and homosexuals, but Herschel makes Clara post them. He is soon met by protesters boycotting his pickle business, and Clara joins them. However, despite the controversy, Herschel earns support from conservative groups who think he is just fighting for free speech. He gets selected to appear for a debate with a college professor on the subject of ethics. Ben crashes the debate and pretends to disguise himself so Herschel won’t recognize him. He asks Herschel a question about Christian prayer, and Herschel proceeds to call the Virgin Mary a prostitute. Cue Herschel being chased down the street by angry conservatives.

With enemies on both sides, people start calling for Herschel’s deportation back to Schlupsk. He has no choice but to run back to Ben for help. He decides to help Herschel cross the border into Canada. When they get close, Ben feels bad and comes clean to Herschel about being responsible for causing all his recent problems. Herschel knocks Ben out and shaves his own beard, pretending to be Ben when border patrol agents show up. He tells the officers that Ben is Herschel, and Ben goes through a hopeless trial that leads to him being sent to Schlupsk, where nobody speaks English and he is completely on his own.

Herschel stays in Ben’s apartment and goes through his things. He looks at the pictures of Ben’s family and finds a drawing from Ben’s childhood. It turns out “Boop Bop” were nicknames he gave to his parents. Herschel, having thought Ben never cared about his family, realizes that that wasn’t true.

Herschel travels to Schlupsk to find Ben staying in a synagogue. He apologizes to him over getting him in trouble. They reconcile and go by a spot that Sarah used to love being at. Herschel tells Ben that Boop Bop’s problem was not that Ben wasn’t good at what he did, but it was that he was too scared of failing his family. The two then start to discuss going into the pickle business together, where they can pickle more than just cucumbers. Herschel likes the idea. The two return to Brooklyn and pay a visit to Sarah’s grave, where they start to pray together.

During the credits, Ben puts on “Yentl” for Herschel, and he finds himself smitten with Barbra Streisand.

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Herschel Greenbaum is an Eastern European immigrant who travels to America with his wife Sarah in 1919 to escape their dreadful home life. While working at a pickle factory, Herschel falls into a vat and remains preserved in the pickle brine for 100 years. He wakes up in the present day and discovers he has a great-grandson, Ben, who is a freelance app developer.

Herschel's old-fashioned way of thinking gets him and Ben in trouble with the law, which leads to them falling out since it ruins Ben's chances of getting funding for an app he's been working on. Herschel decides to start a pickle business by gathering pickles and salt from a dumpster and creating brine with rainwater. The pickles are a big success with New Yorkers, but Ben continues to sabotage Herschel's business by getting him to reveal his bigoted way of thinking.

When all of New York appears to have turned on Herschel for his statements, Ben tries to help him cross the border to Canada, but after Ben confesses that he was trying to sabotage Herschel, Herschel knocks Ben out and assumes his identity, causing Ben to be deported back to Herschel's hometown of Schlupsk. When Herschel goes back to Ben's apartment, he finds out that Ben was making his app in honor of his late parents.

Herschel goes back to Schlupsk to reconcile with Ben and bring him back home, and they decide to go into the pickle business together.