The Roaring Twenties (perhaps accompanied by documentary materials, newsreels etc. about the twenties, the gangster world, etc.)
Alternately the same kind of thing could be done with a set including Little Caesar and The Public Enemy. Perhaps these are among the titles in the upcoming WB gangster films set?
the original 1931 version (AKA "Dangerous Female")
the 1936 version "Satan Met A Lady" (starring Bette Davis)
A 30-minute radio adaptation of The Maltese Falcon on CBS’ “The Lady Esther Screen Guild Players” on September 20, 1943, with Bogart, Astor, Greenstreet, and Lorre enacting their original roles.
The WB cartoon "Hollywood Steps Out."
#2 The Complete Woodstock
Along the lines of Criterion's "The Complete Monterey Pop Festival", this would include the director's cut of the film, plus the "Lost Woodstock Perfomances" laserdisc, the complete Jimi Hendrix performance, and any other material they can license (hopefully all of the Who, the Grateful Dead, and Creedence Clearwater Revival).