Herschel Greenbaum and his spouse, Sarah Greenbaum, are struggling Jewish laborers. They emigrate from their shtetl to America in 1919 after their village is rampaged by Russian Cossacks. Herschel finds a job at a pickle factory, and is able to save up for two graves at a Jewish cemetery. One day, while working at his job, he falls into a vat of pickles as the factory is closed and he is brined for 100 years.
Having woken up in Brooklyn, 2019, Herschel discovers that his only living relative is his great grandson Ben. Ben works as a freelance app developer and is currently developing his own app “Boop Bop”, a service that checks companies’ ethics when buying their products. Ben reluctantly agrees to go with Herschel to the cemetery where Sarah and his son are buried, along with Ben’s parents. Herschel is disgusted to find that the cemetery was left in shambles, along with a Russian vodka billboard overlooking it. This causes him to assault the construction workers putting up the billboard, leading to his and Ben’s arrest.
Ben is able to bail them out of jail; however, he is now unable to get investors for his app due to his new criminal record, causing him to disown Herschel. Herschel decides to begin a pickle business in order to buy and take down the billboard overlooking the cemetery. Herschel’s business is a huge success over social media. However, Ben tells health inspectors that Herschel has been using produce found in the trash bins, causing him to be charged $12,000. Herschel is able to come back from this with the assistance of unpaid interns, causing his business to become even more popular and allowing him to refurbish the cemetery and remove the billboard. Herschel’s success leads to Ben envying him even more.
Ben then tells Herschel to download Twitter, and he begins tweeting controversial statements. While initially met with protests and boycotts, Herschel is then seen as an icon of free speech and empowerment. While Herschel is hosting a friendly debate, Ben shows up and questions his thoughts on Christianity. This leads to a rant about Christianity, causing Herschel to become despised by the public. His immigration files are also not to be found, causing the government to try and deport him.
Herschel arrives at Ben’s apartment, and Ben reluctantly agrees to help him get to the Canadian border. Through this, Ben and Herschel begin to reconcile their relationship. However, Ben admits that he tried to sabotage Herschel’s business, causing Herschel to admit that he is disappointed that Ben is more committed to his app than his family’s legacy, leading to a physical fight between the two. Herschel is able to steal Ben’s backpack, and uses his razor to shave and puts on his clothes to pose as Ben, alerting the police that the real Ben is Herschel. This causes the real Ben’s arrest and deportation.
While at Ben’s apartment, Herschel discovers that the app’s name, “Boop Bop”, was actually the nickname Ben gave his late parents, leading Herschel to realize that family was always in Ben’s heart. He returns to his home country to find Ben, who is staying at a local synagogue. They reconcile, and sometime later return to Brooklyn, hoping to develop a pickle-selling website.