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"Eddie Murphy Delirious" (1983)

OK, technically, "Eddie Murphy Delirious" was an HBO special and not a theatrically released movie, but it warrants a place on the list because the material is still controversial today. Murphy's act opens with some scathing homophobic humor, including a rumination on Mr. T as a gay pedophile. The comedian has apologized for these remarks since. Still, there's plenty of great stuff to be found here. The Michael Jackson impersonation is killer. Just 22 years old when this movie was shot in Washington, D.C., it's like a time capsule of Murphy at his youngest, angriest and hippest. In the 70-minute show, the f-word is used 230 times and the s-word is used 171 times. Four years later, the comedian would top his own obscenity record with "Eddie Murphy Raw," which received a nationwide theatrical release.

The Ugh!

"The Adventures of Pluto Nash" (2002)

This is the largest bomb of Murphy's career (which, as you'll soon see, is saying something) and one of the biggest box office failures of all time. Written in 1985 and rewritten dozens of times by several writers, the movie sat on the shelf for two years after filming wrapped before finally offering itself to the public in 2002. It landed with a resounding thud. The production budget was more than $100 million. The movie grossed less than $5 million domestically. Ouch. The film has a terrific supporting cast, including Rosario Dawson, Peter Boyle, Pam Grier, John Cleese and Jay Mohr. The premise concerned Murphy's character searching the universe for the culprit who destroyed his intergalactic nightclub. A repeated joke in the trailer about Hillary Clinton's face being on American currency sealed the deal. Nothing about the film was funny and it was a terrible idea to begin with.

"Daddy Day Care" (2003)

Recently, Murphy has starred in a handful of lame family comedies ("The Haunted Mansion" anyone?), but "Daddy Day Care" represents a whole 'nother brand of yuck. It's a movie that anyone could have starred in. The comedian looks trapped the entire time. All of the humor involves bodily functions and pratfalls that even newborn babies don't find amusing anymore. Yet somehow the film grossed more than $100 million, proving yet again that you can't go broke appealing to the lowest common denominator. The movie was even popular enough to green light a sequel, which wasn't as successful. In a strange turn of events, Murphy's role was recast in the second film with Cuba Gooding Jr. If that's what a Best Supporting Actor Oscar gets you, perhaps it's a good thing Murphy didn't win for "Dreamgirls" after all.

"Harlem Nights" (1989)

Here's a great idea: Let's put three terrific comedians together in a movie that isn't a comedy and where all of them have to legitimately act the entire time. Wait a minute. That doesn't sound like a good idea at all. Sadly, no one had this foresight when Paramount approved "Harlem Nights," which starred Murphy alongside Richard Pryor and Redd Foxx in a story about crime syndicates and police corruption in the 1920s. The movie was written and directed by Murphy. It was his filmmaking debut. It also ended up being his filmmaking swan song, although a cult fan base for the movie lives on. The industry viewed it as a vanity project. It was the first truly damaging step down in the actor's career, setting off a string of midlevel failures in the early '90s that wasn't broken until "The Nutty Professor."

"The Golden Child" (1986)

Chalk up the first stumbling block in Murphy's career to unreasonably high expectations. "The Golden Child" isn't nearly as bad a movie as people make it out to be. It's just infuriating because it misses a bunch of great chances to be entertaining. It could be an adventure flick or an East-meets-West comedy or a child abduction tale. In the end, it's none of these things. It settles for being a run-of-the-mill action comedy that doesn't bear any imprint of its star's presence. Despite questionable reviews, the film still grossed just under $80 million. It plays on AMC all the time, which is admittedly kind of sad. Commercial breaks between all the poorly organized inanity might actually help this thing out, though. Then again, maybe not.

"Norbit" (2007)

Let's get real: This is the movie that cost Murphy an Oscar. Had the ads for "Norbit" not been lining billboards and subway stations exactly when the Academy Award ballots were being mailed to voters, there's a good chance Murphy would've walked away with the prize instead of Alan Arkin. Another multiple character outing, "Norbit" is a disturbing experience. It's so painfully bad but so inherently watchable that you actually hate yourself for enjoying it. It's a testament to Murphy's talent that anyone made it through the thing with brain intact. The comedian was criticized for exploiting racial stereotypes in the movie, but the film isn't just offensive to black or Asian Americans. It's offensive to anyone using their time or spending their money to sit through it. Ironically, "Norbit" was nominated for an Oscar for Best Makeup earlier this year. It didn't win.

Many great Murphy performances didn't make the list. Which one should've been substituted in for something else? Did you secretly love "Pluto Nash"? Send your thoughts to heymsn@microsoft.com

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In addition to making regular contributions to MSN Movies, Frank Paiva is a senior at New York University, where he studies theater and writing. His work has appeared in The New York Times, the Seattle Weekly, the Not for Tourists New York guide, go2 Mobile, and EDGE.