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4. King Kong (2005)

Whereas I’m sure most people have stopped reading for panning their beloved Dances, it became a popular sport to hate on Peter Jackson’s first project after the completion of the Lord of the Rings trilogy.

The movie just does not work, even though Jackson, like most directors in this position, had his heart in the right place. The beautiful New Zealand and Pacific sceneries that adorn the picture are indeed breathtaking, and some of the CGI animation was innovative 10 years ago. But if there is a movie that suffers and becomes undone by its unnecessary length, it is precisely this one.

Why do they have to have such long scenes with Naomi Watts and the beast alone? Why the three different endings and climaxes and goodbyes towards the end? Indeed, in true Jacksonian fashion (he nearly ruined Return of the King this way), it feels like the movie ends at least a half dozen times, and then it keeps going and going and increased pain and agony. At the very least, a much stricter pair of scissors in the cutting room would have helped this movie immensely.

3. Pearl Harbor (2001)

Of the movies on the list, the one that arguably ended or ruined the most careers is the 2001 disaster Pearl Harbor. Michael Bay? Josh Hartnett? One of them is relegated to making terrible after terrible Transformers Movie, the other is…who is the other one?

It is hard to explain what went wrong with what could have also been one of the best movies of all-time. Fresh off the heels of the successful Armageddon and hailed as maybe the next Titanic, Pearl Harbor had all the elements to succeed and make a mark in movie history. And the disaster sequences of the attack themselves are pretty solid and bone-tingling. But it is the unbearable romance/triangle between the trying-too-hard-not-to-look-disheveled (but with purposefully disheveled hair) Hartnett, the always pouty Kate Beckinsale, the in-your-face acting Cuba Gooding Jr. (there’s another ruined career), and the unemotional Ben Affleck, that certainly takes some of the blame.

The movie is also disjointed, told in two parts - the first being the attack and the second the Doolittle Raid (led by Alec Baldwin dialing it in for the most part) - which hurts the overall investment needed to allow the audience to sit through 180+ minutes of a film. In the end, Bay used his Armageddon style (perfect for a mostly slap-sticky movie about the end of the world) in a movie with a much more personal, historical, and important subject matter to its audiences. It ended up treating that subject, not intentionally, like a roller coaster ride or an amusement park and naturally, audiences did not respond well to that.

2. The Great Ziegfeld (1936)

Perhaps a tad obscure to be on this list, I remember almost smashing the television as the 1936 Best Picture winner came to a close. The movie is a musical biopic that loosely chronicles the life story of theater magnate Florenz Ziegfeld. Not only is the movie boring, for the most part, it reeks of the exaggerated production value that was still common in Hollywood in the era. It simply has not aged well.

The movie has exaggerated dance numbers, exaggerated songs and choreography, and exaggerated claims of grandeur regarding its central figure, who is portrayed as almost godlike, flawless, and infallible. For a 90 minute parody or fictionalized account, it would work. But, at three hours (in some cuts, anyway), one expects nuance and depth from the characters, not jumping around like it’s a circus.

I always remember this Best Picture winner as “that circus” movie, even though that really is The Greatest Show on Earth (an actual movie about the circus). That is not a good sign.

1. Cleopatra (1963)

Elizabeth Taylor and Richard Burton are one of the most infamous celebrity couples of the 20th Century, and the epic Cleopatra one of their most notorious and colossal failures. The movie was expensive and a complete flop with audiences. For good reason.

It is not only that it is too long for what the movie is about, it is that it bombasts everything it does in every way. Like others on the list, from Pearl Harbor to Ziegfeld, the movie is simply too over the top in showiness and too shortcoming in emotional and intellectual depth. By the time the beautiful Elizabeth Taylor undergoes yet another costume change (research revealed she had a Guinness World Record 60 something wardrobe movements in the film), it’s not clear whether you are watching a movie or a beauty pageant.

Rightfully, one is awed by the magnificence of the production values, and who does not love to see the real-life lovers sexually joust as Cleopatra and Marc Anthony? But the narrative is tedious and overexposed, the screenplay oxymoronic while, somehow, even condescendingly simplistic, and the acting is not the best showcase for the otherwise reliable Taylor and Burton. It is no wonder that the movie was such a colossal failure, given the production difficulties that plagued it as a longtime Taylor passion project; it is only a wonder that people didn’t burn down the theater in protest.

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