Throughout his long career, Clint Eastwood has had a number of iconic roles. He's been a boxing coach, a man with no name, a secret service agent, and an outlaw. He is perhaps best known however for playing a cop, Inspector 'Dirty' Harry Callahan.

Harry Callahan, a San Francisco police detective, was featured in five separate films from 1971 until 1988. He battled street thugs, organized crime, and more than one less-than-sane individual, and through it all he carried with him his trusty .44 Magnum, or, as he called it, “the most powerful handgun in the world.” Harry Callahan was the prototypical “cop on the edge.” He battled lieutenants and mayors as hard as bad guys, and his partners had a terrible way of winding up injured or worse.

The first film in the series, Dirty Harry, is unquestionably the best in the franchise. Directed by Don Siegel (Two Mules for Sister Sara), the film is a hard-nosed, straight, tough, cop movie. It, more than any of the sequels, seems to truly inhabit San Francisco, making the city almost a bystander to the murder and mayhem that takes place within it. As Callahan, Eastwood grits his teeth and snarls his way to a brutal, harsh ending that was inevitable from the moment Harry's prey, a sniper, executed his first victim.

From the next film, Magnum Force, to The Enforcer, Sudden Impact, and finally The Dead Pool, the films become progressively weaker. Partners, the best of whom was Tyne Daly in The Enforcer, come and ago, but Harry is unchanging. Harry faces down new bosses and loses partners with the same regularity that most of us change our socks.

That would be okay — there's some humor in seeing Harry argue with every Mayor of San Francisco that the citizens choose to elect — but the problem is that the argument is unchanging. From the first movie to the last, the warning Harry receives is something akin to “the city of San Francisco is changing. Your brutal methods, which worked at one time, will no longer be tolerated. I, your lieutenant, won't accept them, the mayor won't accept them, and the good people of San Francisco won't accept them.” Harry then goes out and kills people, but still manages to find himself on the force at the start of the next film. It all becomes a bit clichĂ©d by the third movie.

Of course, anything beyond bloodlust in his character is hugely variable from film to film. The system doesn't work for Harry in the first film, so he takes matters into his own hands. By the second film he shows that he still believes in the system and is against police becoming judge, jury, and executioner. However, down the line, in the fourth film, he seems more accepting of vigilantism in general.

Each of the films in the series features a decent amount of shoot 'em up excitement, with people being dispatched in new and sometimes interesting ways. It's just that by the fifth film, the series has become a caricature of itself. It's more about scenery chewing with bits of humor thrown in than a possible looking-glass reflection of our society. Jim Carrey, even with little on screen time, doesn't work as a drug-addled hardcore rocker, especially when lip-syncing “Welcome to the Jungle.” And, when the scariest thing Harry faces in the whole movie is a remote control toy car with a bomb, it seems as though a good decision was made in not resurrecting the franchise for a sixth go-around.

The biggest letdown in the films is not the fact that they become silly or derivative at any point, but rather their incredibly poor representation of women. In Harry Callahan's world women are purely sexual, psychotic, or just plain weak. Even Tyne Daly's appearance as Harry's partner in The Enforcer does little to bolster the franchise's depiction of women. Even if it did, the depiction instantly goes back to nil with Sondra Locke's rape victim turned killer in Sudden Impact.

The recently released, remastered DVDs make a well put together set. The original film is a two-disc edition and all the films contain commentary tracks (but only The Enforcer has the director, James Fargo in that film's case, providing the track). There are also more featurettes than one can shake a stick at, with examinations of Harry's place in society and film history, looks at violence in movies, and examinations of Eastwood's career. True Dirty Harry fans can purchase a single boxed-set “ultimate collector's edition” which features an extra DVD that has a feature length documentary on Clint Eastwood, a brief hardcover book, a replica Dirty Harry wallet (complete with police badge), a reproduction (miniaturized) of a one-sheet, production correspondence, and a poster-sized map of San Francisco that shows Harry's hunt for Scorpio, the killer in the first film.

The truly amazing thing about Dirty Harry, is just how iconic a figure he really is. There are actually bits and pieces of all five movies that are memorable in their own right; heck, it isn't until Sudden Impact, the fourth film (and only one in the series directed by Eastwood) that Harry says the classic line, “Go ahead, make my day.” Watching the films, listening to the commentary tracks, and viewing the featurettes in the DVD collection one can see reflections of Harry and the films Harry inspired through the present day.

As a reflection on our world and our times, one could do better than watching the Dirty Harry movies. At least early on, the films do have a strong point of view about where our society is headed. It's not a pleasant view, and hopefully one that has been proven wrong, but it is there.

Dirty Harry is, without a doubt, a product of his times. The filmmaking, not the plots, do still stand up today, but Clint Eastwood is really the reason to watch these movies. He appears in each film with as much seriousness and grit as he can possibly muster. Even in a bad movie, he is good to watch.