It’s logical to have expected activity in the film world over the issue of gays in the military. Most of the films have been small, and there may have been missed opportunities.
One of the oldest was a television film, “Matlovich vs. The U,S. Air Force” on NBC in 1977, about Tech Sgt. Leonard Matlovich.
One of the first important Clinton era films was “Serving in Silence” on NBC, about the case of Washington National Guard colonel Grete Cammermeyer, as played by Glenn Close. I remember a scene near the end where the Army JAG lawyer for the government describes her as a fine person.
There was talk in the 1990’s that there would be films about both Joseph Steffan and Keith Meinhold, but they did not come about.
An important film about tension within the ranks. would be “Any Mother’s Son” on Lifetime, in 1996, about the murder of gay sailor Allen Schindler, from the Belleau Wood, by off-duty sailor Terry Helvey in Sasebo, Japan, in 1992, a killing that was in the same league as that of Matthew Shepherd.
In 2003, Showtime aired “Soldier’s Girl”, the tragic story of a solider (Barry Winchell) who fell in love with a trangendered person (Calpernia Adams) and was bludgeoned to death by unit mates, at Fort Campbell, KY.
In 2008, Johnny Simmons produced an important documentary “Ask Not” giving the history of the “Don’t Ask, Don’t Tell” policy,
There is a similar film in 2009 by Tom Murray, titled “Tell”, having mostly interviews of soldiers, and attorneys including Dixon Osburn.
Ned Farr’s “A Marine’s Story” presents a lesbian kicked out of the Corps telling her backstory as she trains a delinquent girl with tough love.
“Out of Annapolis”, by Steve Clark Hall, presents gay alumni of the Naval Academy.
In 2012, Marc Wolf produced the film “Don’t Ask, Don’t Tell” on Snag Films, his monologue based on his play “Another American: Asking and Telling”, which I had seen at the Studio Theater in Washington DC in April 2000.
The best history film on the policy is probably “The Strange History of Don’t Ask, Don’t Tell” (Fenton Bailey and Randy Barbato) on HBO, airing in October 2012. The film did a particularly good job of distinguishing between the “privacy” issue and “unit cohesion”, which is a bit more subtle.
And there is the one hour history “Do Ask, Do Tell: The Documentary” on YouTube by Ali Sue.
There are many films in the past that have tangentially brushed the issue of gays in the military, including the 1929 silent classic “Wings” set in WWI, and even “A Few Good Men” in 1992.