Jackie Brown (Miramax, 1996)
Or should we now refer to it as "the third film by Quentin Tarantino"? A character comedy in the guise of a crime thriller, Jackie Brown is a long love letter to blaxploitation icon Pam Grier. The two-disc DVD is loaded with fun stuff: QT interviews, MTV appearances by the cast, and more than a dozen trailers for Grier's 70s films, leading to the question "How many of those Filipino-women-in-prison pictures did Grier make?"
Rushmore (Criterion, 1998)
There are two Rushmore DVDs on the market. You want the Criterion, which costs twice as much as the bare-bones Touchstone DVD but has three times the stuff: a commentary by director Wes Anderson and co-author Owen Wilson, auditions and screen tests, Anderson's obsessively detailed storyboards and the MTV Movie Award recreations of Armageddon, Out Of Sight and The Truman Show by the Max Fischer Players.
Amélie (TF1/Miramax, 2001)
A beautifully constructed DVD made in the spirit of the film it surrounds, which is either an irresistible sweet-toned fantasy or a toxic charm dump. Included are Audrey Tautou's screen test, the director's commentaries in English and French, a gallery of the garden gnome's travel Polaroids, cast interviews and short films.
A Bug's Life: Collector's Edition (Pixar/Disney, 1998)
One could pick any of the Pixar packages - Monsters Inc. has the funniest outtakes and best menus, and the Toy Story three-disc box is awesome - but A Bug's Life is my favourite Pixar movie, in part because of the jaw-dropping cast. Kevin Spacey as the leader of the grasshoppers! Denis Leary as the ladybug! Also, I'm a sucker for unofficial remakes of The Seven Samurai. Great extras, including a sound-effects-only audio track and the usual Pixar behind-the-scenes stuff.
Fight Club (20th Century Fox, 1999)
The two-disc special edition (the "brown paper" cover) is officially out of print, but it's still out there. Great transfer, four commentaries, complete promotional gallery and an assortment of extras that systematically undermine the experience of watching the film - a catalogue of 'fight club" wear, for example.
The Matrix (Warner, 1999)
There was a time when if a person owned a DVD player, odds were one in three that he also owned a copy of The Matrix, the first great hit of the digital age. Even after the sequels and the fact that the film's signature moments have been copied and parodied to death, The Matrix is still a visual extravaganza and more fun than any philosophically pretentious dystopian action movie has a right to be.
Memento: Limited Edition (Columbia TriStar, 2000)
Chris Nolan's backwards-unfolding story of a man in search of revenge but unable to form new memories has either the coolest or the most annoying second disc of any special edition. Working through the menus to get to things like the chronological cut of the film is like trying to unravel a Rubik's cube.
Terminator 2: The Ultimate Edition (Artisan, 1991)
Theoretically superseded by the "Extreme" edition, with its version that can only be played on a Windows Media 9 player, the Ultimate still contains the greatest Easter egg of all time. There's the theatrical version, the extended DVD cut and the hidden, even longer, third cut of the film accessed by punching in the "Judgment Day" date at the appropriate point in the menu.