Top 10 Embarrassing Movies Made By Legendary Actors

Every actor is bound to make a stinker or two over the course of his or her career. Heck, if you’re looking at someone like Nic Cage or John Travolta, he’s bound to make a dozen or more, and let’s not even get started on someone like Emilio Estevez or his esteemed uncle, Joe.

But, some actors have such a tremendous history of making excellent choices that you wouldn’t expect them to ever make a horrible movie. Of course, even the greatest actors throw a gutter ball now and then. Such as…

10. Helen Mirren – Caligula

Ah, Dame Helen Mirren. The older woman that every man still thinks is hot, and who every woman thinks is super classy and, also, still hot. At this point in her career, Mirren can do pretty much any film she wants and it immediately jumps up a notch in terms of prestige, even if that movie involves her firing a giant machine gun. No, especially if it involves her firing a giant machine gun.

But, there was a time when that was not always the case. Like, you know, with the 1979 film Caligula. All you need to know about the movie is the fact that one of the producers was the founder of Penthouse. It actually had a superb cast, featuring the likes of Peter O’Toole, John Gielgud and Malcolm McDowell in addition to Mirren, and the script was developed by Gore Vidal, but the fact is the movie was basically a full on porno. Obviously a movie about Caligula is going to be racy, but did you ever think there’d be a movie in which Dame Helen Mirren gets super naked and has all kinds of kinky things going on? The only reason it’s not higher on the list is the fact that Mirren herself seems okay with it, considering she recorded commentary for the extremely controversial film.

9. George Clooney – Return of the Killer Tomatoes

There was a time when George Clooney was just another big headed actor trying to make his way in Hollywood, picking up the occasional movie role in between guest shots on shows like The Facts of Life and Roseanne. Well, one of those movie roles was 1988’s Return of the Killer Tomatoes, the sequel to a campy horror movie that approximately 12 people saw in the first place.

Believe it or not, there were multiple sequels to the original campy, cult classic Attack of the Killer Tomatoes, but only one starred the man who would go on to become his generation’s Cary Grant, Mr. George Clooney himself. There is not point in getting into the plot, because with a movie in which humanoid tomatoes are engineered by a mad scientist and begin attacking people, is there really any point? Clooney likely looks back on this and laughs it off, because in addition to being super wealthy, super handsome and super cool, he’s also got a super sense of humor, which makes us super hate him that much more. Stupid Clooney. (Clooney appears at the end of the trailer – 2:07.)

8. Marlon Brando – The Island of Doctor Moreau

Let’s face it, Marlon Brando, rest his soul, was pretty much a joke for a long time toward the end of his career: partially because he was a humongous jerk (supposedly), …and also that he was just humongous. Seriously, the guy apparently ate everything in sight. Legend has it that if a horse wandered too close, half of it would be gone before it could whinny a horrible, strangled cry for help.

Even with his late life reputation, he was one of the greatest actors who ever lived. That’s why it’s beyond baffling that he made the utterly horrendous Island of Doctor Moreau. Based on the classic book of the same name, the film was strange and confusing, even when you take into consideration the bizarre subject matter of a mad scientist who creates animal/human hybrids. Brando’s performance, and his weird little sidekick in the film, was so weird that they spawned the character of Alfonz Mephesto and his little friend Kevin on South Park.

7. Tom Hanks – The Bonfire of the Vanities

Just after he was Tom Hanks, comedic megastar and right before he became Tom Hanks, dramatic powerhouse and Oscar vacuum, Tom Hanks tried to break into the world of dramatic acting in the 1990 adaptation of Tom Wolfe’s book The Bonfire of the Vanities. Hanks co-starred with Bruce Willis and Melanie Griffith in the movie, which featured Tom as a Wall Street big shot who accidentally put a Bronx youth in a coma in a hit and run.

The whole movie is supposed to be taking on race relations, and we suppose it’s something of a precursor to movies like Crash. It might not be as horrendous as some of the other films on this list, but consider this: it also featured Morgan Freeman and F. Murray Abraham and was supposed to be a smash success only to become one of the biggest bombs in movie history, failing with both the critics and the general public. But it’s okay, Tom Hanks, we still love you anyway.

6. Anthony Hopkins – Freejack

Back in the day, Anthony Hopkins was nothing more than a beloved stage actor who was tremendously well respected in England but didn’t have a lot of pull in American cinema. Then, of course, came The Silence of the Lambs, and everything changed. Suddenly he was one of the most respected actors on the planet, able to pick and choose his roles and gain critical acclaim in virtually everything he did.

So he chose to risk squandering all of that by appearing in the Emilio Estevez and Mick Jagger movie Freejack just one year after winning an Oscar for his portrayal of Hannibal Lecter. This science fiction movie took place in the super far off distant future of 2009, and involved time travel and rich people striving for immortality. Estevez stars as a race car driver sucked into the future just before a deadly crash, and of course 2009 is basically a dystopian wasteland, and Hopkins is the villain who probably had a mustache that he twirled menacingly when he revealed his true motives. We’re not really sure, it’s been a while since we’ve seen it. The fact of the matter is that Hopkins chose to follow up his Oscar win with this crap, and yet here we are mocking Cuba Gooding for making Chill Factor. Sorry, Cuba.

5. Ben Kingsley – The Love Guru

There was a time when Mike Myers was a respected actor and comedian, and it wasn’t viewed as a gigantic embarrassment to be in one of his films. That time was not 2008, and one of those films was not The Love Guru. That didn’t stop Sir Ben Kingsley – yes, he’s been knighted – from jumping right into a role in the so-called “comedy” which also featured Justin Timberlake and won the Razzies for Worst Picture and Worst Actor.

Kingsley, who won an Academy Award for his titular performance in Gandhi, became part of an exclusive club with his performance in The Love Guru: only a few Oscar winners have gone on to nominated for a Razzie for an acting performance. Kingsley is fantastic in just about everything he’s ever been in, but is certainly not immune to making horrible movies now and then, and we’re not just talking about this one. Yes, Ben “I was also in Schindler’s List” Kingsley, we remember BloodRayne, too. (Watch for Kingsley 1 minute into the video.)

4. Gary Oldman – Tiptoes

Over the years, Gary Oldman has proven to be one of the most reliable, diverse actors out there. He can perform Shakespeare, he can lend credence to any comic book movie, and he can flat out disappear into any role that comes his way. He’s superb in every sense of the word, with perhaps the high point of his career coming with his Oscar nominated performance in Tinker Tailor Soldier Spy.

With all of that said, holy crap, you guys have got to check out Tiptoes. Seriously, check out the video clip, because if you don’t you’ll swear we’re making it up. Go on, we’ll wait. Did you watch it yet? Are you seeing that? Yes, this movie actually exists. Oldman costarred with Matthew McConaughey and Kate Beckinsale in a movie in which Oldman plays a freaking dwarf. Not like a Lord of the Rings dwarf, but an actual, Warwick Davis-esque dwarf and the younger brother of McConaughey. We can’t really do justice to how absurd the movie is, but amazingly it actually screened at Sundance to what we assume was slackjawed silence.

3. Robert DeNiro – Rocky and Bullwinkle

Sometimes a live action adaptation of a beloved children’s show can be decent, and even pleasant. Not often, but it’s certainly within the realm of possibility. Of course, in most instances those films star smaller actors trying to break into the big time, or TV stars trying to make the transition to the big screen. They sure as hell never star the guy who was in Taxi Driver, Godfather II, Raging Bull or Goodfellas. Right?

Hey, we get that Robert DeNiro has been trying for a while to show his versatility and let people know that he can play more than just a mobster and a thug. The problem is, while DeNiro has some comedic chops, we don’t really want to see him in any other sort of role. He’s one of the greatest actors of all-time, so do we really want to see him sully his reputation by popping up in the horrendous live-action meets animation adaptation of Rocky and Bullwinkle? Yeah, we’re going to go ahead and say no.

2. Michael Caine – Jaws 4/On Deadly Ground

If there’s one thing Michael Caine knows how to say, it’s something witty and cheeky in a tremendous cockney British accent. If there’s one thing Michael Caine doesn’t know how to say, it’s the word “no.” Seriously, just look at the guy’s IMDb resume. It’s pretty clear that Michael Caine has never met a movie offer he doesn’t like, as evidenced by his participation in Jaws 4 (The Revenge) and On Deadly Ground.

Jaws The Revenge, quite frankly, is one of the least necessary and overall dumbest sequels ever made. If you haven’t seen it, lucky you, but here’s the general plot: Mrs. Brody and her surviving kids are down in the Bahamas, and we’re supposed to buy that some sort of relative of the a Great Whites her late husband killed has tracked her down and is hell bent on seeking revenge. Yeah, it’s as dumb as it sounds. And let’s not get started on Caine appearing in On Deadly Ground, other than to say he plays the villain in a Steven Seagal movie. Just let that sink in for a minute before you go watch him in Dark Knight Rises this summer.

1. Al Pacino – Jack and Jill/Gigli

Video NSFW (language)

Just like Michael Caine and potato chips, we were unable to pick just one when it comes to Al Pacino. That’s what happens when you’ve starred in two of the worst movies ever made, which is exactly what the artist formerly known as Michael Corleone did when he first co-starred in Gigli and then recently made the abomination that is Jack and Jill. It’s amazing that a man can star in two of the greatest movies ever made in Godfather and Godfather II, and then go to the complete opposite end of the spectrum with these two pieces of pure, unfiltered excrement.

We’re trying to figure out what prompted Pacino to take roles in either of these two movies, because unlike Caine we’re pretty sure Pacino knows how to say no when an offer comes his way. Was it the fact that he was just dying to work with Ben Affleck and Adam Sandler? Did he have tremendous gambling debts and needed a payday? Or is he just trying to screw with us by making us ask these very questions? We may never know. And we also may never watch another Pacino movie after having witnessed these two atrocities.

Did we miss any good ones? Let us know and we might add it to our TopTenz YouTube playlist of…

Embarrassing Movie Roles

By Jeff Kelly

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