Adam Sandler’s 2011 comedy Jack and Jill opened to an impressive $25 million at the box office. Why was that impressive? Because Jack and Jill also opened to nearly universal negative reviews, garnering a paltry 3% fresh rating on Rotten Tomatoes.

Of course, the fact that Jack and Jill was a huge critical disappointment shouldn’t be all that surprising. Anyone could have guessed that critics would hate the movie from its first trailer. The one thing about Jack and Jill that is shocking, however, is the fact that Al Pacino stars in the film.

How could Pacino, who starred in movies like The Godfather, agree to be in a movie like Jack and Jill? It just doesn’t make sense. Then again, there are plenty of great actors who have starred in terrible films.

Ask almost anyone to name the best actors of all time and you’ll probably hear names like Robert De Niro, Marlon Brando, or Jack Nicholson. But even those great actors don’t have spotless records when it comes to the silver screen. In this article, Screen Rant takes a look at the worst movies from some of the best actors.

First, a few disclaimers:

  1. We cut this list down to the 15 greatest actors based on Academy Award wins and nominations. The Oscars aren’t perfect, but it was the simplest way to get a (fairly) objective list.
  2. We left out some famous actors that were at their best in the 1930s and 1940s (sorry Spencer Tracy!).
  3. Lastly, in order for a film to qualify as an actor’s “worst,” it has to have had at least 10 Rotten Tomatoes reviews. Many of these actors have starred in lesser-known films that ranked lower than the ones we have listed, but these movies didn’t have enough reviews to provide a fair representation of their awfulness.

Now that the legal disclaimers are out of the way, let’s get things started with the man that inspired this list in the first place.

With one Academy Award win and eight nominations, not to mention unforgettable roles in movies like The Godfather, Al Pacino definitely deserves a spot in the “greatest actors of all time” discussion. However, the living legend has fans and critics scratching their heads over his decision to appear in the Adam Sandler comedy Jack and Jill.

Starring as a bizarre version of himself, Pacino’s “character” is supposed to have a romantic obsession with Jill – a screechy terror played by Adam Sandler in drag. Interestingly, Pacino makes it work – sort of. By some accounts, Pacino’s oddball performance is actually the best thing in the film, which, to be fair, isn’t saying much.

While the movie was a financial success in its opening weekend, Jack and Jill is one of the worst-reviewed films of the year and inspired some critics to joke that the Apocalypse was upon us. I don’t know if Jack and Jill represents the end of days, but I do know this: it ranks as Pacino’s worst ever (and that’s really saying something, since Pacino also starred in Gigli).

Like Al Pacino, Robert De Niro made a name for himself as an actor in the 1970s through gritty roles in movies like Taxi Driver and Raging Bull. As he’s aged, however, De Niro seems to have taken his foot off the gas pedal and coasted on his reputation a bit.

That’s not to say I blame him. With several iconic roles and an Academy Award under his belt, De Niro’s legacy as one of the all-time greats is already locked into place.  Still, with The Bridge of San Luis Rey and Godsend, De Niro should probably have taken a step back and rethought things.

On its surface, The Bridge of San Luis Rey probably seemed like a great idea. Not only was the movie based on a well-known Pulitzer Prize-winning book, but it also featured a well-known cast, including numerous other Oscar winners. Despite these plusses, however, the movie failed to impress critics and only screened for 21 days at a paltry 6 movie theaters. The horror film Godsend was somewhat more successful, but was widely criticized for its implausibility and brazen disregard for science.

Nobody does it quite like Jack. Over the course of his more than 50-year career as an actor, Nicholson has been a part of several iconic films and has the accolades to prove it. Among living male actors, nobody has more Academy Award wins and nominations than Jack Nicholson (3 and 12, respectively) and few can claim to have as many instantly memorable lines.

Of course, when you’ve been working for over 50 years you’re bound to have a few screw-ups, and Nicholson’s worst was a movie called Man Trouble from 1997. The film, which earned him a Razzie nomination, re-teamed Nicholson with director Bob Rafelson, who had found success collaborating with the actor on multiple movies in the 1970s, including the excellent Five Easy Pieces.

Unfortunately, this Nicholson-Rafelson partnership didn’t work out as well, becoming a huge flop both commercially and critically. The movie’s romantic comedy plot (about a man who runs a guard dog service and his relationship with a celebrity client)  was criticized for being lightweight and failed to connect with audiences.

Tom Hanks is more than just one of Hollywood’s nicest guys, he’s also one of its best actors. Whether you’re watching the slapstick comedy of his early career or a deeply emotional performance in a film like Philadelphia (for which he won an Academy Award), it’s simply hard to recall a time when the two-time Oscar winner hasn’t given a good performance.

There’s at least one though: The Bonfire of the Vanities. This ill-fated 1990 adaptation of Tom Wolfe’s famous book had a strong cast (which also included Bruce Willis and Melanie Griffith) and a good director (Brian De Palma), but was a huge flop with critics and audiences.

Criticized for its poor casting (Hanks as a mean-spirited Wall Street investor?) and loose interpretation of the original novel’s dark and bitter themes, The Bonfire of the Vanities was a good reminder that great ingredients don’t always make a great meal.

Sean Penn’s intense acting style has earned him two Academy Awards and an impressive five nominations, but the actor does have some notable flops on his resume. Skilled at taking on complex and morally ambiguous characters, Sean Penn struck out with his performance as Willie Stark in the 2006 film adaptation of All the King’s Men.

For a little background: All the King’s Men was a 1946 Pulitzer Prize-winning novel about a corrupt populist politician (who was based on the real life politician Huey Long). The story, which has already been turned into an Academy Award-winning film in 1949, is the type of prestige fare that most actors would kill for. So how did something that worked so well before fail so miserably for Sean Penn?

According to most critics, the 2006 film was boring, confusing, and overly serious. Penn in particular was criticized for a melodramatic performance. You know when an actor is really trying to win an Academy Award? That’s what Penn was doing in this movie, and the result was an inauthentic performance.

With two Academy Awards to his name, Daniel Day-Lewis is undoubtedly one of the finest actors in modern cinema. He’s also one of the most finicky. Known for being extremely selective about the films he stars in, Day-Lewis has a nearly perfect track record when it comes to picking starring roles. He did have one high-profile miss, though, with the 2009 musical Nine.

Nine, which was adapted from a stage play (which was itself adapted from Fellini’s brilliant film 8 1/2), had the potential to be a big Chicago-like musical success. Unfortunately, the movie’s confusing plot didn’t connect with audiences or critics and the film was a big flop at the box office earning $53 million – well short of its $80 million budget.

Interestingly, despite its relative shortcomings, Nine was still nominated for four Academy Awards. Compared to some others on this list, Daniel Day-Lewis is coming out pretty well, which says a lot about the actor and the careful approach to his career.

Jack Nicholson once famously said, “When Marlon dies, everybody moves up one.” Indeed, nobody on this list can come close to matching Marlon Brando’s status as a cultural icon and, in his prime, few could match him as an actor. While Marlon Brando’s career is marked by famous movies like On The Waterfront and The Godfather,  the actor also starred in some stinkers and the 1992 film Christopher Columbus: The Discovery was one of Brando’s worst.

Unlike the Nina, Pinta, and the Santa Maria, this movie was sunk from the beginning due to financing issues and behind-the-scenes drama. Of course, the lackluster performances didn’t help the movie’s cause either. Brando in particular phoned in his performance, which was not all that uncommon for the actor during his late career.

Obviously, Brando’s failed performance in a largely unknown period film hasn’t had an impact on his legacy, which is good. We all want to remember Marlon Brando as the soulful actor of A Streetcar Named Desire, not as an overweight, tired old actor that was just cashing a paycheck.

One of several actors on this list to study with the famous Lee Strasberg, Paul Newman turned his steely blue-eyes and affable demeanor into a hugely successful movie career, earning 10 Academy Award nominations and one win. However, while Newman is best known for his work in classic films like The Hustler and Cool Hand Luke, the actor didn’t always pick the best projects.

There are a couple of films from Newman’s early career that earned a rare 0% fresh rating on Rotten Tomatoes, but since these films don’t have the requisite number of reviews, we ended up with the 1999 romantic drama Message in a Bottle.

Newman actually earned strong critical praise for his role as Kevin Costner’s father, but the movie’s contrived plot and depressing ending didn’t connect with critics. Still, Message in a Bottle did decent business at the box office which is more than what most of the movies on this list were able to accomplish. The fact that this is one of Paul Newman’s worst movies really speaks to the actor’s skill and longevity.

Dustin Hoffman is widely recognized as one of the best actors of the last 50 years, thanks to memorable performances in films as diverse as The Graduate, Rain Man, and Tootsie. Not so memorable was the two-time Academy Award winner’s role in the 2010 film Little Fockers. Although Hoffman had his share of decent jokes, most critics ravaged Little Fockers for being an unfunny retread that did little to improve upon the two previous films.

Alongside fellow Academy Award-winner Robert De Niro, Hoffman probably made a mistake in agreeing to come back to star in the third Fockers film. Then again, the movie was a huge box office success, earning $310 million against a $100 million budget, and you can’t blame actors for taking the easy payday once in a while, especially when their legacy is already secure.

Two-time Oscar winner Jack Lemmon is one of those rare actors that found as much success late in his career as he did early in his career. In his earlier films like Some Like It Hot and The Odd Couple, Lemmon demonstrated superb comic timing. The actor didn’t miss a beat many years later when he re-teamed with Odd Couple co-star Walter Matthau for the 1993 film, Grumpy Old Men.

Unfortunately, the surprise success of Grumpy Old Men didn’t translate to the film’s 1995 sequel, Grumpier Old Men (at least with critics who said it was an unfunny rehash). However, while Grumpier Old Men was a critical flop, it was a big hit with audiences. Like the first film, Grumpier Old Men earned an impressive haul at the box office on a relatively meager budget, proving that critics don’t always get it right.

There aren’t too many people out there who don’t like Denzel Washington. In my opinion, the worst thing you can say about him is that he takes on too many similar roles (which is a moot point, since he’s usually awesome in them).

However, while the actor’s powerful performances have earned him five Academy Award nominations, not all of Washington’s work has been well-received by critics. This is especially true for the film John Q. Though it was a box office success and a huge hit with regular audiences, the film was poorly received by critics who believed that the film forced its agenda in an awkward and overbearing manner.

Frankly, of all the films on this list, John Q feels the most out of place. While the critics have a point about the movie’s lack of subtlety, the film is undeniably affecting and Washington is excellent in the role. If John Q is considered one of Denzel Washington’s worst movies, then the two-time Oscar winner is doing fine.

With one Academy Award win (out of five nominations) and important roles in such monumental films as The Godfather and Apocalypse Now, Robert Duvall is easily one of the most celebrated character actors in movie history, which is why it’s so curious that the 2003 Civil War film Gods and Generals was such a miserable failure.

For those not up on their Civil War movie history, Gods and Generals was a prequel to the 1993 film Gettysburg. Unlike the first film, however, Gods and Generals failed to weave an interesting drama out of its heady subject matter, leading critics to complain about the film’s plodding pace and ridiculously long runtime (a whopping 214 minutes).

Taking over for Martin Sheen, Duvall did a decent job filling the role of General Robert E. Lee, but the movie’s lack of narrative focus doomed it with audiences. The $55 million film, which was entirely financed by billionaire Ted Turner, was a failure at the box office earning just shy of $13 million domestically.

While Michael Caine’s working-class British charm has earned him two Academy Awards and featured roles in everything from Austin Powers to Inception, the actor’s considerable talents were unable to elevate the ridiculous Steven Seagal action film, On Deadly Ground.

The film, which Seagal also directed, was the worst kind of vanity project. Centered on a renegade employee’s efforts to protect a group of native Eskimos from the greedy oil company, the movie was excoriated by critics and did little to establish Seagal as a legitimate actor. The only way On Deadly Ground works is if you watch it as part of a Steven Seagal drinking game.

In addition to On Deadly Ground, Caine also earned terrible reviews for his work in Jaws 4: The Revenge. On the plus side, at least Caine knew his performance was awful. As he later remarked, “”I have never seen it, but by all accounts it is terrible. However, I have seen the house that it built, and it is terrific!”

When Jeff Bridges finally took home an Academy Award in 2009 for his starring role in Crazy Heart, everyone in Hollywood seemed to breath a sigh of relief.  After six nominations, it was great to see the talented actor finally get recognition for his consistently dignified and eclectic work.

However, not all of Bridges’ eclectic film choices proved popular with critics. In particular, the 2005 independent film The Amateurs – about a group of small town men interested in filming an amateur porn film – failed to connect with critics and earned the actor some of the worst reviews of his career.

One other film on Bridges’ resume could also fill be considered his worst: the 1985 thriller 8 Million Ways to Die. However, that film, which earned the dreaded 0% fresh rating, only has seven reviews so we’re leaving it off the list. In either case, if you’re looking for a good Bridges movie, we recommend checking out some of his more popular films. Big Lebowski anyone?

Morgan Freeman’s stately voiceovers are practically a staple of any good dramatic film and the actor has starred in plenty of them. But the five-time Academy Award nominee (and one-time winner)  has also been known to star in some pretty bad movies as well.

More than any other actor on this list, Freeman seems content to do any project if it means cashing a paycheck. That’s not a criticism, just an accurate observation. How else could you explain his appearances in the 1996 action film Chain Reaction. Co-starring Keanu Reeves, Chain Reaction was criticized for being a generic action film with a convoluted plot and average acting.

Basically, Chain Reaction was one of those movies where everybody thought, “Meh.” It didn’t make you want to gouge your eyes out, but it didn’t do much else, either. In a sense, it was a precursor to the kinds of mindless action movies Freeman would appear in in the future (like the equally awful Hard Rain).

What do you think of these “worst film” picks? Do you agree or disagree with any of them? Also, what other great actors have some terrible credits to their name? Sir Ben Kingsley comes to mind, as does Kevin Spacey. Anyone else? Feel free to debate in the comments.