Brazil ( Criterion, 1985)
The only argument against including Brazil in this list is the possibility that Criterion might decide to do anamorphic remasters of the two separate and very different prints of the film, the 142-minute director's cut and the 90-minute "love conquers all" version proposed by Universal studio boss Sid Scheinberg, included in this three-disc set. The middle disc has Jack Mathews's documentary The Battle Of Brazil, which recounts in exacting detail the fight between director Terry Gilliam and the studio.
From Dusk Till Dawn (Dimension, 1996)
The second disc of this Tarantino/Robert Rodriguez vampire flick contains Full Tilt Boogie, a casually demented documentary about an itinerant film crew stuck in a small hotel in the middle of nowhere. One of the best making-of docs ever, because it isn't focusing on the genius of the creators or even the making of the film in question.
Magnolia (New Line Platinum, 1999)
If you're not exhausted by Paul Thomas Anderson's 188-minute epic about a day in the life of a dozen characters in the San Fernando Valley, put on the second disc for That Moment: Magnolia Diary, Mark Rance's 75-minute video diary. See Anderson and then girlfriend Fiona Apple argue; watch Anderson address the film ("You're too long and don't have an ending"). Hear Bill Macy's comments during a hyperbole-crazed junket ("You know, Paul ground the lenses for the film...").
Twelve Monkeys (Universal, 1995)
It's no accident that documentary filmmakers are drawn to Terry Gilliam. He seems uniquely willing to let people see the worst moments of his productions. Running 90 minutes, The Hamster Factor And Other Tales Of Twelve Monkeys follows the film from pre-production to marketing focus groups, and may be the best making-of documentary of the past decade, unless one counts Lost In La Mancha, which is by the same filmmakers and has the same director at its centre.
Singin' In The Rain (MGM/Warner Video, 1952)
Of all the PBS/History Channel/TMC documentaries that have found immortality as DVD supplements, few have more value than Musicals, Great Musicals: The Arthur Freed Unit At MGM, from PBS's American Masters series, about the creative core of MGM when it produced Singin' In The Rain.