Washington Irving's story Rip Van Winkle was first published in 1819. The trope of someone falling asleep/under a spell/unfrozen caveman lawyer is as old as storytelling itself, and this trope is the basis for An American Pickle. Rogen plays Herschel Greenbaum, a ditch digger in a village in Eastern Europe in 1919. He marries Sarah, but on their wedding day the town is destroyed by Russian Cossacks, and it's on to America for Hershel and Sarah.
They want to get rich - for Sarah enough to buy her own gravestone, for Herschel, he just wants to try seltzer water. Herschel gets a job at the pickle factory, making enough to buy a small burial plot for the Greenbaums. His job is killing rats with a club, but one day a multitude of rats drives him to fall into a vat of pickles, just as the factory is condemned. Two kids find and awake him in the abandoned factory, in 2019, the pickle brine having kept him the same as he went in and in fine shape.
Herschel meets up with his great grandson, Ben (also played by Seth Rogen), who has a place in Brooklyn and has spent five years developing an app called Boop Bop, which gives companies ethical scores. The fish out of water part with Herschel is not overdone; he's not as interested in the new tech as the fact that Ben owns over 30 pairs of socks. Also, Ben has a Soda Stream so unlimited seltzer! Ben's parents are dead and Herschel drags him to the Greenbaum burial plot, now decrepit and stuck between highways, strewn with weeds and garbage, and with a huge billboard hanging overhead.
Herschel says prayers for the dead, Ben seems to have lost his faith, and when a crew shows up to put a new billboard (Russian vodka) on the sign, Herschel believes they are Cossacks and gets into a big fight. He and Ben are arrested for assault and this ruins Ben's reputation as an ethical coder. He's now unable to sell his app.
Ben and Herschel are at odds, and there's a lot going on. Herschel declares he will make $200,000 to buy the billboard and cut it down. Using items found in dumpsters, including cucumbers, he makes his own pickles (just cucumbers, salt and rainwater). His little pickle cart in Williamsburg takes off. Ben calls the health department and Herschel is shut down. Herschel bounces back by using a small army of NYU interns, gets the pickle business up to code, and makes the money he needs to cut down the billboard and clean up the Greenbaum plot.
There's a lot of silliness in this movie, but it has a sweet, heavier undertone of family and especially Jewishness. Herschel is not the smartest fellow, but he is a hard worker that puts family above all. He's also very religious.
When Herschel says some truly awful things about Jesus in a debate, he is the newest victim of cancel culture. He gets Ben to smuggle him to Canada, but pulls a switcheroo, Ben is arrested as the wanted Herschel and deported; Herschel returns to Brooklyn as “Ben.” The real Ben, back in Eastern Europe, gets in touch with his Jewish heritage and spends time in the synagogue. Herschel goes through some old pictures of Ben’s and realizes the Boop Bop app is named after Ben's parents. Herschel returns to Eastern Europe ( “Alexa told me how to get here”) to get Ben. They realize they are family and must stick together. The movie ends back in Brooklyn with both men saying prayers for the dead at the Greenbaum plot.
This was a surprisingly touching and sweet movie, despite all the silliness. Rogen was obviously struggling with his own Jewish identity, and this is a great love letter to his ancestors. Showing on the can-you-get-it HBO Max, you could do a lot worse than An American Pickle.