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The 10 Most Disappointing Movies of All Time

Stick with me here— there’s a Bowie connection coming (two, actually)…

Several days ago I mentioned in a post that the 1967 comedic version of Casino Royal might be the worst movie of all time. I think that’s actually correct, but picking the worst movie is tricky. The first challenge is distinguishing the worst movies from the movies that I personally don’t like. Though I only saw it once, in my mind, Babette’s Feast is near the top of the list of movies I didn’t like, though it was critically acclaimed and would be a tough case for it to objectively be called bad.

The second and larger issue has to do with expectations. The very earliest movies, like the brief footage of a train coming into a station (the 1895 film clip today known as, Arrival of a Train), basically just show off what at the time was a new technology. These clips can be appreciated for their historical value but can’t really hold up as movies compared to any later movie with, you know, a plot and acting. But a lot— the vast majority of those movies, too, don’t compete against each other on equal footing over time. Acting styles, technology, precedent, conventions and just about everything else evolved over time, so its unfair to weigh the quality of say, the original King Kong to, say, Jurassic Park, without grading on a curve for King Kong’s originality. What would later become trite and derivative would have been fresh the first time it was done.

Expectations, too have a lot to do with genre. While a handful of horror movies are widely recognized as great movies (say, Silence of the Lambs or The Exorcist), the vast majority serve their purpose at the drive in, for teenagers out on dates or for cheap thrills. The same for monster movies, romantic comedies, superhero movies and so on. Any attempt to compare Friday the 13th Part 2 with Citizen Kane just isn’t going to work. Both do what they are supposed to do, but they are very different forms of entertainment.

Next comes the Ed Wood problem. The somewhat well-known and legitimately funny book, The Golden Turkey Awards, names Wood’s 1950s science fiction movie, Plan 9 from Outer Space, as the worst movie of all time. I have seen Plan 9, and it is indeed bad. Many people have seen Plan 9, because it’s so bad, its good. Well, its not good. But its funny. Anyway, nobody will see Plan 9 and expect it to be a great movie, so, while The Golden Turkey’s case against Plan 9 is both logical and very funny, I think its a mistake to actually put that movie and that type of movie on the same continuum with anything anyone would expect to be decent.

Finally, before I get to my list, there’s a whole group of films that are bad because of their content. Birth of a Nation and Triumph of the Will are technologically innovative movies, but the first celebrates the Klan and the second literally glorifies Hitler. In both cases, there are aspects of the filmmaking that are accomplished, but they are bad movies in the sense that they carry with them evil messages.

So, the “worst” movie is truly going to be tough to peg. I’m going to instead rank what I think are the 10 most disappointing movies, at least for me, that I’ve ever seen. There are worse movies out there, but I haven’t seen every movie there is to see. And no, Godfather III is not going to be on this list. Godfather III is disappointing— but the following stinkers are much, much worse:

1. Casino Royale (1967). This is the Bond parody based off the actual plot of the Ian Fleming novel of the same name, the same as the excellent 2006 film, also titled Casino Royale. The framing gag of this movie is that there’s an ensemble cast including David Niven, Woody Allen and Peter Sellers, all of whom are going around calling themselves “James Bond.” With additional stars including Ursula Andress, Orsen Welles, and a bunch of others you would recognize, this one should have at least been funny. But multiple directors and screenwriters turned it into a mess. We had to wait for Austin Powers before we got a good Bond parody.

2. Dracula: Dead of Loving It (1995). Mel Brooks is the master of the parody movie. Young Frankenstein has a strong case to be the funniest movie ever. Brooks has been funny for 70 years. Teaming up with Leslie Nielsen should have made it simple— instead it’s like this movie was made by the living dead. There are maybe one or two funny gags in the whole thing, despite Brooks’ attempt to replicate what usually works for him, a machine-gun of what are supposed to be jokes, images, ideas… all this usually works, but not here. Probably the biggest distance between expectation and result.

3. Yellowbeard (1983). So is Young Frankenstein the funniest movie? Or is it Monty Python and the Holy Grail? This movie has the stars of both, so it must be hilarious, right? Graham Chapman, John Cleese, Eric Idle, Peter Boyle, Madeline Khan, Marty Feldman, plus Cheech and Chong and… David Bowie (in a cameo). Again, there are a handful of funny moments, but the expectation was for this to be the next Life of Brian. It isn’t.

4. Star Wars: The Phantom Menace (1999). This movie is probably more famous for being reviled than anything else on this list and thus requires less of an explanation. What stands out for me, though, is that I grew up with the original trilogy and saw this as if I had been waiting half my life for it. My expectation was so high that I didn’t realize how truly awful the movie was upon first viewing— I wanted to like it. But its so bad that the annoying little boy who plays the child Darth Vader was obscured by the offensively hideous CGI character Jar Jar Binks (I get a shudder from even typing the name).

5. Meet Wally Sparks (1997). Rodney Dangerfield is next on the list of great, iconic comedians who was also capable of dashing expectations. Actually, Rodney might have more misses than hits. For every Caddyshack or Back to School, there are many largely forgotten movies like, The Fourth Tenor and Lady Bugs. So why did I choose Wally Sparks for this list? Well, I couldn’t make it all the way through The Fourth Tenor and didn’t even give Lady Bugs a try. I paid money to see this one in the theater, and that’s both $5.00 and and hour and a half of my life I will never get back. Totally unfunny.

6. Twin Peaks: Fire Walk With Me (1992). Twin Peaks was the last network television show I watched during its first run, on network television. I had high hopes for the movie, which were elevated when I found out David Bowie would be in it! Alas, he’s in it for less time than it has taken you to read this far and the movie is a nonsensical mess. To the extent I remember it, it is essentially irrelevant to the ongoing story of the show and doesn’t stand up on its own.

7. Holmes and Watson (2018). Not even Sherlock Holmes could detect the missing humor in this movie. Another bad parody starring two usually very funny comedians — this time Will Ferrell and John C. Reilly. Should have been hilarious. Throughout the movie, the two seem like they are trying to be funny. Uncharacteristically, however, they just fail. Jaw-droppingly bad.

8. Mean Streets (1973). Not only is Martin Scorsese one of the most consistently great filmmakers of the last fifty years, but this movie is beloved and widely acclaimed. Because of all that, I was terribly disappointed— and bored— when I finally got around to seeing it. Yes, the movie has atmosphere. Yes, its characters are characters. Yes, it introduces the word, “mook,” to a larger audience. But if you can describe to me the plot, please let me know. Better yet, let me know why (other) people like this one so much.

9. The Last Days of Patton (1986). Patton (1970) is actually my favorite movie. The performances of George C. Scott and Karl Malden are beyond iconic. So expectations were high when I learned of this made-for-TV sequel. I can say this for the movie— it is appropriately named. Scott, as Patton, spends most of his time on his deathbed reminiscing. The move has less to do about his leadership or role in World War II than…actually I don’t remember. To make matters worse, missing is the Jerry Goldsmith soundtrack that is an essential element that made the 1970 movie so impactful. A four-star letdown.

10. Babette’s Feast (1987). OK, I said this was too widely acclaimed to be objectively bad. but this list is not objective. All the high praise is why I saw the movie in the first place. More than 30 years later I have very little memory of the movie, but it left the indelible impression in my head that it is my least favorite movie of all time. That’s quite an impression.

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