The filming location for Harvey Milk's business, Castro Camera, was the real storefront where the actual business had once been. At the time of filming (mid-2008), it was a gift shop called "Given"; the film crew worked with the owner of the gift shop to recreate the look of Milk's camera store inside the space and restored it to its 2008 appearance after filming.
During the sequence dealing with Proposition 6, one of Milk's friends says "Even Reagan doesn't support it." Former Governor Ronald Reagan was so opposed to the measure that he publicly went against the Republican Party on the issue, even though he had been mentioned as a serious candidate for the Presidential election in 1980 and risked alienating his conservative support base. His support was given a great deal of credit for Proposition 6's defeat and contributed to his growing national profile ahead of his two elections as President of the United States.
The last public appearance of Harvey Milk's life, two days before he was killed, was attending a San Francisco Opera performance of Puccini's opera "Tosca" featuring the legendary Italian soprano Magda Olivero, on Saturday, November 25th, 1978. Not only is this event depicted in the movie, but it was in honor of that appearance that the filmmakers chose to use "Tosca" for all the operatic music heard in the film.
The film made Roger Ebert's year-end list of the 20 best movies of 2008. Ebert did not rank his picks that year, opting instead for an alphabetical list. He later said that the film was the most deserving of all the Best Picture Oscar nominees.
According to Josh Brolin, the scene where Dan White is on his underwear looking scared through the window was not scripted like that, but was just the result on actor and director trying different things to convey White's state of paranoia.
Veteran police officer and actor Brian Danker, seen in this movie in his first speaking role in the homicide scene, actually served in Vietnam from 1970 to 1971 in the same unit as Dan White - the 173rd Airborne.
It was widely reported that while filming a scene at the old Castro Camera, some of the actors claimed that they saw a man come in and sit on a couch. After the scene was filmed, nobody else claimed to have seen the man, and the actors themselves went on to claim that it was perhaps the ghost of Harvey Milk.
During a July 2008 interview with the Orange County Register about Pineapple Express (2008), the interviewer told Seth Rogen and James Franco that he prepared for the interview by watching the classic stoner comedy Fast Times at Ridgemont High (1982) the night before. When he asked Rogen and Franco if they prepared likewise before making Pineapple Express, Franco said he prepared by making out with Spicoli (a reference to his having filmed Milk (2008), in which he and Sean Penn play lovers).
The movie starts out with Harvey Milk talking into a tape recorder on Saturday, November 18th, 1978, the same day as the Jonestown Massacre. The People's Temple was based in San Francisco before departing for Guyana in 1977.
In 2016, while a guest on the National Public Radio program "Fresh Air," Cleve Jones told the interviewer Terry Gross that several weeks before filming on Milk began, he and Emile Hirsch (who played him in the movie) met and started spending time together so that Hirsch could base his portrayal on the real Jones: "I got to show him my neighborhoods and places I'd lived. We had meals together. We became friends. And it's a peculiar sensation to know that you're being watched by an actor who's going to portray you. And I will say that there was one moment...when I'm driving around town and I suddenly realized that I was trying to butch it up. I was so horrified when I realized what I was doing. That's when I took him back and made spaghetti and said, now listen, you know, OK, I'm a big old queen but I'm not a cartoon. I'm not a caricature, and you better get this right. But he did, he did. I loved the movie."
Some of the clothing worn in the movie by Sean Penn was borrowed from Gilbert Baker, a friend of Harvey's. Gilbert Baker is famous for being the creator of the Rainbow Flag, the symbol of the LGBTQ+ Community. His clothes were another authentic piece of history added to the movie.
Deliberately released two weeks before California voted on Proposition 8, a referendum to overturn the legality of gay marriage. California passed the proposition, though this has since been overturned.
Developed concurrently with "The Mayor of Castro Street" which was scripted by Oliver Stone with Bryan Singer attached as director. This project was ultimately shelved, torpedoed by the writers' strike.
The trivia items below may give away important plot points.
At the end of the film, images of the actors costumed as their characters are replaced by photographs of the real people the actors portrayed. Many of these photos were taken by Daniel Nicoletta, who is the photographer played by Lucas Grabeel in the movie.
Daniel Nicoletta: The real Danny Nicoletta has a cameo in the film as the person in Harvey Milk's office just before Harvey Milk was assassinated by Dan White. In real life, Nicoletta was the last person to speak to Harvey Milk in his office at San Francisco City Hall, shortly before Harvey Milk was assassinated, perhaps the same moment Dan White assassinated mayor, 'George Moscone (I)', that Monday morning, November 27th, 1978.