Vertigo is Hitchcock's best film and arguably the best film of all time. It's certainly the single greatest work of craftsmanship, audience manipulation, and cinematic language ever filmed. It's also one of the greatest moral explorations of film as a medium yet-produced.
The central theme in this film, which often goes ignored, is a kind of meta-commentary on both filmmaking and "star-making." If Inglourious Basterds is Tarantino's wild, uneven, and disorganized treatise on the power and danger of image creation (in IB's case, most specifically w/r/t history and history-making), Vertigo is Hitchcock's interrogation of the same--but with a much more honed, subtle, and personal focus. Vertigo is, above all else, about the power and destructive capacity of artifice and fantasy on the explicitly human (rather than the global) level. In many ways, the most similar film to Vertigo is David Fincher's the Game, which treads similar narrative and thematic ground, except it's not very good.
Rear Window is Hitchcock's earliest overt (and his most obvious) interrogation of "cinematic ethics" and his first film in which implication of the spectator (a theme explored in Vertigo and taken too far in his later work: e.g. Marnie) is the central theme. Vertigo does Rear Window one better. While Rear Window's window-as-movie-screen conceit is an obvious metaphor for and exploration of cinematic voyeurism and obsession and it hooks you on this concept from the start, Vertigo lets you go along for the ride with Ferguson for half the runtime, and then the film's subtext is delivered later--and in a more subtle payload. The same beautiful fantasy that entrances Ferguson entrances you--and Hitchcock's use of familiar narrative tropes and expertly placed POV shots (alongside his standard limited range of narration) align you so closely with Ferguson that you want (for the film's first half), almost as desperately as he does, for the whole bizarre fantasy to be real.
If the first half of the film is the fantasy, the latter half is its deconstruction. In the key scene where Judith's true identity is revealed to us but not Ferguson, Gavin is essentially also revealed as a sort of pseudo-filmmaker, who presents Ferguson with a wonderful but impossible story to cover up his wife's murder. The brilliance of the film's construction is that it drives a wedge between the audience and Ferguson at this juncture by giving the audience privileged narrative information (that Judith is Madeleine). Our knowledge of Judith's true identity (which comes before Ferguson's own realization of it) transforms Ferguson from a dramatic protagonist to more of a tragic one. (In Marnie, by contrast, the audience remains aligned with Mark even as he essentially rapes Marnie--which makes the film that much harder to watch and far more abrasive, unpleasant, and inelegant than Vertigo is.)
In many ways, Ferguson's later attempts to transform Judith into Madeleine are analogous to the contemporaneous Hollywood star-making process: her physical transformation is portrayed as painful and drastic and, ultimately, she is forced to lose her identity to become an inauthentic figure of fantasy and obsession. Ultimately, Ferguson's tragedy is that the beautiful story of mystery and death in the film's first half (the same one that is so attractive to us, the audience) leads him to recreate the story in his own mind, to the extent that he not only recreates Madeleine but also kills her once more. If, in Rear Window, Hitchcock is asking to what extent cinematic voyeurism is truly a one-way street, in Vertigo he's asking to what extent the beautiful violent fantasies films present can repeat themselves in their spectator's lives--while also revealing the pain and artifice behind the fantasies themselves. The whole film is a story of spiraling, circuitous obsession--a metaphor for the madness and obsession of making such a film, but also of falling prey to its beautiful, deceptive fantasy.