- Matt Damon was originally cast as Dan White, but had to back out due to scheduling conflicts with Green Zone (2010).
- Thousands of people agreed to take part in the film as extras for free.
- 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 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 shot Milk (2008/I), in which he and Sean Penn play lovers).
- 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.
- Proposition 6 was defeated in part due to the intervention of former California Governor, but not yet President, Ronald Reagan. Reagan spoke out publicly against the initiative and turned a great deal of public opinion against it. This is also viewed as the origin of the Log Cabin Republicans.
- Director Gus Van Sant has been involved with the making of Harvey Milk projects for over fifteen years. For his unsuccessful attempt to film The Mayor of Castro Street (2011) in the early 1990s, many actors were under consideration for the role of Harvey Milk including Robin Williams, Richard Gere, Daniel Day-Lewis, and James Woods.
- 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.
- During the filming of the scene in which Dan White's son Charles is christened, the real Charles White was on the set.
- On Roger Ebert's year-end list of the 20 best movies of 2008. Ebert did not rank his picks this year, opting instead for an alphabetical list. (He later said that Milk (2008/I) was the most deserving of all the Best Picture Oscar nominees.)
- On the American Film Institute's year-end list of the 10 best movies of 2008 (this list is decided by a group of film scholars, journalists, and professionals, including Jeanine Basinger, Mark Harris, Elvis Mitchell, Daniel Petrie Jr., Richard Schickel, Robert Towne, and Leonard Maltin).
- Number 2 on Lisa Schwarzbaum's Entertainment Weekly Magazine list of the 10 best movies of 2008.
- Number 9 on Owen Gleiberman's Entertainment Weekly Magazine list of the 10 best movies of 2008.
- Sean Penn's cosmetic transformation in the film included a prosthetic nose and teeth, contact lenses and a redesigned hairline. His makeup was done by Academy Award winner Stephan Dupuis.
- Actor Denis O'Hare who plays ant-gay Senator John Briggs in the film is in reality openly gay.
- The real Cleve Jones has a cameo in the film as Don Amador.
- The apartment that was used in the film is the real apartment Harvey Milk lived in on the Lower Haight in San Francisco.
- Scott Smith's last name is never mentioned until the epilogue, and Jack Lira's last name is only given in the credits.
- Cameo: [Carol Ruth Silver] The real Carol Ruth Silver has a cameo in the film as Thelma.
- When Gus Van Sant was planning a biopic of Milk in the early 90's he offered the part of Cleve Jones to River Phoenix, who he had just worked with on My Own Private Idaho (1991).
- Sean Penn became only the ninth actor to win two Academy Awards for Best Actor after winning for this movie.
- Josh Brolin doesn't appear until 45 minutes into the movie.
- 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. 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.
- After his first kissing scene with James Franco, Sean Penn texted his ex-wife Madonna saying, "I just broke my cherry kissing a guy." (Her texted response: "Congratulations.")
- Cameo: [Dustin Lance Black] The screenwriter appears as one half of the couple that walks by the Castro camera shop after it's closed, when Harvey Milk is inside and one of the men asks if Harvey was going to win this time.
- Bradley Cooper auditioned for the role of Scott Smith.
- Chris Evans auditioned for the role of Scott Smith, but lost out to James Franco.
>>> WARNING: Here Be Spoilers <<<
Trivia items below here contain information that may give away important plot points. You may not want to read any further if you've not already seen this title.
- SPOILER: 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.
- SPOILER: CAMEO(Daniel Nicoletta): The real Danny Nicoletta has a cameo in the film as the person in Harvey Milk's office before Milk gets assassinated by Dan White.
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