Superhero movies tend to come in just one of two flavors: Exceptional and terrible.

They either work as visually breathtaking, escapist fun… or they don’t. This summer features a slew of upcoming superhero movies, including The Wolverine and Kick-Ass 2. The latest, Zack Snyder’s highly anticipated Superman reboot, Man of Steel, soars into theaters on Friday.

The movie tells Superman’s origin story, with Henry Cavill (“The Tudors”) stepping into the iconic title role, Amy Adams as his perennial love interest Lois Lane and always creepy Michael Shannon as big bad General Zod. The impressive supporting cast includes Kevin Costner, Diane Lane, Laurence Fishburne and Russell Crowe. Will Man of Steel fare better than the franchise’s last reboot, 2006’s middling Superman Returns? Hard to say at the moment, but we’ll find out soon enough whether this latest Superman soars into the heavens or plummets down to Earth.

To celebrate Man of Steel’s release, join us as we take a look back at some of the best and worst superhero movies of the past two decades.

Worst

Steel (1997) super2

1997 saw the release of two horrible superhero movies—the lesser-known being this DOA story about a military weapons designer (Shaquille O’Neal) who builds a suit of armor (hence his alter ego name, “Steel”) to fight crime (a swipe from Iron Man, perhaps?). The character of Steel originated in a Superman comic book series; judging by the film adaptation, this is one superhero who should have stayed on the page. As Steel, Shaq redefines the meaning of the word “stiff.” Perhaps tired of being known solely as a star basketball player, Shaq tried his hand at a number of different art forms in the 1990s—acting, rapping—albeit none of them well. (Anyone remember the cinematic treasure Kazaam or the classic rap album “Shaq-Fu: Da Return”? We didn’t think so.) On the other hand, this turkey’s failure probably saved us from seeing Shaq embarrass himself in a string of terrible sequels. Let’s just say Shaq shot an air ball with Steel.

Batman and Robin (1997) 

The other horrible superhero flick of 1997 had a significantly higher budget and anticipation factor than Steel, making its failure all the more disappointing. With its campy tone, tacky sets (which seemed more suitable for a gaudy Las Vegas show than a big-budget comic book adaptation) and jokey, unthreatening villains (played by “The Governator” himself, Arnold Schwarzenegger, and Uma Thurman), this film obliterated the gothic mood of Tim Burton’s earlier Batman movies and regressed back to the over-the-top excess of the 1960s TV series. Even George Clooney, the third actor to get behind the wheel of the Batmobile for Hollywood, was unhappy with the results, saying “I think we might have killed the franchise” and calling the film “a waste of money.” Luckily, the franchise wasn’t left for dead, and in 2005, the series was rebooted with Christopher Nolan’s acclaimed Batman Begins.

Catwoman (2004)

Soon after nabbing an Oscar win for Monster’s Ball, Halle Berry apparently wanted to show her range and go in the opposite direction by appearing in this piece of dreck. Inspired by the classic DC Comics character, Catwoman tells the story of a shy woman who walks a thin line between criminal and hero after being endowed with the speed, reflexes and senses of a cat. With its laughable dialogue and sloppy action sequences, the movie was a bomb with both critics and audiences, winning four Golden Raspberry awards (including Worst Picture and Worst Director for the singularly-named Pitof, who, not surprisingly, hasn’t helmed a feature film since). Berry was a surprisingly good sport, accepting her win for Worst Actress in person, with a speech that summed up how many feel about this abysmal re-imagining: “First of all, I want to thank Warner Brothers. Thank you for putting me in a piece of shit, godawful movie… It was just what my career needed.”

Best

Spider-Man 1 & 2 (2002, 2004)

Stan Lee and Steve Ditko’s classic comic book creation was faithfully adapted into these fun films, which have lots of potent web-slinging action in addition to a heavy dose of heart. Tobey Maguire proved perfect casting as gawky teenager Peter Parker, who, after being bitten by a genetically-engineered spider, finds himself with super-human powers, including increased strength, speed and the ability to climb walls. Director Sam Raimi’s trademark giddy, hyperkinetic camerawork proved a perfect match for the films. While Spider-Man 3 suffered from a sense of being rushed and overstuffed, the first two films are superhero tales at their best. And the franchise continues to grow. In addition to the controversial, much-delayed musical “Spider-Man: Turn Off the Dark,” a successful 3-D reboot of the series was released last summer, with Andrew Garfield (The Social Network) stepping into Spider-Man’s tights, and a sequel, The Amazing Spider-Man 2, is slated to hit theaters next year.

Iron Man (2008)

Another classic Stan Lee comic series made a successful big screen transition, thanks in large part to Robert Downey Jr.’s funny, charismatic performance as weapons manufacturer-turned-superhero Tony Stark. With Jon Favreau behind the camera and a dynamite supporting cast(including Gwyneth Paltrow and Jeff Bridges), Iron Man provides a large amount of fun. Its worldwide success proved that such mass entertainments have the ability to appeal to both adults (who dug the film’s hip, witty sensibility) and kids (who loved the video game-esque action scenes). Since then, two megahit sequels have been released, and Tony Stark also popped up in last year’s superhero smorgasbord, The Avengers, with a sequel scheduled for 2015. As good as some of these films have been, though, none quite captured the effortless fun of the original Iron Man, which still holds up as an example of superhero moviemaking at its most entertaining.

The Dark Knight (2008)

Director Christopher Nolan successfully re-imagined Batman for a new generation with Batman Begins, starring Christian Bale as the tortured superhero. Last year’s The Dark Knight Rises brought the trilogy to a satisfying close but it’s the second film in the series, The Dark Knight (a.k.a. the Citizen Kane of superhero flicks), that stands as a towering achievement—proof that superhero movies have the capacity to be not only great entertainment, but great works of art, period. The movie finds Bruce Wayne taking on his most dangerous foe yet—insane criminal mastermind The Joker (the late Heath Ledger, in an Oscar-winning role), who is hell bent on unleashing anarchy throughout the world. With its complex characters and storyline, intense action sequences and dark, foreboding tone, The Dark Knight is a shining example of what superhero movies can—and should—be.

Have a fave (or least fave) superhero movie not covered above? Let us know in the comments!

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