10 Worst Jack Black Movies, Ranked

However, as with any acclaimed actor who has been a part of the industry for decades, Black has also had his fair share of critical misfires that failed to land with audiences or critics alike. Whether it be long-forgotten fragments of his early acting career before he truly found his footing and hit his stride or more modern attempts that fail to recapture and capitalize on the actor's inherent strengths. While he will surely continue to be an icon of comedy filmmaking, with upcoming works such as Minecraft and Anaconda, these career low-points make his greatest work that much better by comparison.

10 'Saving Silverman' (2001)

Directed by Dennis Dugan

One of many by-the-numbers raunchy romantic comedies that defined the 2000s, Saving Silverman does very little to set itself apart from other similarly styled films of the era. The film follows a trio of long-time best friends who find that their friendship could end when one of them is about to be engaged to a woman who wants nothing to do with the other two of the trio. Now, this pair of buddies will have to team up to save the third in their trio from a painful marriage to the absolute wrong woman who threatens to break them up.

While Black attempts to do his best to add an allure of wild comedy and hijinks to the film, Saving Silverman's outright mean-spirited approach to comedy makes it difficult to watch in the modern era. While the duo of Black and Steve Zahn are usually enough to make certain scenes stand out, the vast majority of the film is focused on the much more uninteresting and ineffective Darren Silverman (Jason Biggs).

9 'Bongwater' (1998)

Directed by Richard Sears

As far as stoner comedies of the 90s are concerned, few are as deeply unimpressive and forgettable as Bongwater, a film whose low budget and lack of good vibes get in the way of making it a true classic. The film follows the blossoming couple of David and Serena who soon have their simple, melancholy life completely thrown for a spin when David's house burns down, leaving Serena to leave him and run off to New York. In an attempt to help deal with the pain, David turns to the sweet comfort of marijuana as he chills out with a group of his close friends to forget about his troubles.

Black plays the role of Devlin in the film, one of David's friends who helps him get in touch with his inner self during his marijuana-fueled recovery. While Black manages to provide a bit of limelight into the film with an effective comedic song on the acoustic guitar, it isn't enough to save the overall experience from being largely dull and forgettable. The majority of the film focuses on this sour, underwhelming relationship, a far cry from the zany stoner comedy that it presents itself as in marketing.

8 'Dear Santa' (2024)

Directed by Bobby Farrelly

One of the latest comedy misfires by Jack Black, Dear Santa proves that a film has to do more than simply retread the same schtick that Black has been doing for decades to find success for modern audiences. The film follows a young, dyslexic 6th grader who, when writing a letter to Santa, accidentally misspells his name and addresses his letter to Satan, lord of the underworld. Later that night, Satan himself arrives to help the young boy deal with his struggles at school in hopes of retrieving the young boy's soul.

While the concept of Jack Black playing Satan in a wild holiday comedy seems like it would make for a fun time, the film fails to utilize all the creative possibilities to be a rather generic holiday affair. Despite the posturing and buildup, the vast majority of Satan's magical help doesn't go much farther than some raunchy toilet humor, painful celebrity cameos, and a half-baked feel-good message. While it isn't one of the worst Christmas movies of all time, it's certain to be forgotten by the time that the season ends.

7 'Shark Tale' (2004)

Directed by Vicky Jenson, Bibo Bergeron, and Rob Letterman

One of many voice acting roles that Black would take on over the years, Shark Tale has proven to be one of the lowest points throughout the entire filmography of Dreamworks Animation. The film follows a small ocean fish Oscar (Will Smith), who finds himself in deep trouble with various powers and superiors around him, who ends up finding the solution to his problems via a friendship with Lenny (Black), a vegetarian shark. The lie ends up both transforming Oscar into an unexpected hero and allowing Lenny to hide from his duties and expectations as a vicious great white shark.

Shark Tale as an animated film took away all the wrong lessons from previous successes like Shrek and served to just be a constant array of pop culture references and an unsettling animation style. The film's strange, mobster fake death fish story proves to be too overly complicated and strange to connect with, growing to be more cumbersome and tiring as it goes on. Black himself rarely does enough to elevate the film, with the voice that he gives Lenny being rather annoying and directly going against his strengths as a comedic actor.

6 'Shallow Hal' (2001)

Directed by Peter and Bobby Farrelly

A polarizing and painful romantic comedy experience that is fully emblematic of the culture and comedy senses of the early 2000s, Shallow Hal was a moderate success when it was first released, but is one of the most poorly aged comedies of all time. The film sees Black as Hal, a pompous man with ludicrously high standards for what he wants out of a partner, yet his lifestyle suddenly changes after a run-in with a self-help guru that makes him see people by their inner beauty. Hal now finds himself lovestruck by Rosemary (Gwyneth Paltrow), without even realizing that she's 300 pounds and far from a supermodel.

Shallow Hal has one of those gross, unappealing plots for a romantic comedy that even feels uncomfortable to write about, blatantly playing into egregious beauty standards in an arguably misogynistic lens. While the film attempts to tell an honest and effective message about inner beauty and worth, its execution in saying that only skinny, beautiful women are deserving of love and affection is deeply gross and uncomfortable to watch.

5 'The Neverending Story III' (1994)

Directed by Peter MacDonald

One of Black's first notable appearances in the world of filmmaking, his villain role in The Neverending Story III couldn't save the film from being a monumental disappointment. The film sees a now 13-year-old Bastian dealing with the difficulties of moving into a new neighborhood, starting high school and being the target of a notorious group of bullies known as the Nasties. During one of his daring escapes from the Nasties, he ends up finding a way to return to the legendary world of Fantasia, yet the Nasties soon find the book and place the whole world into chaos.

Black plays the role of Slip in the film, the leader of the Nasties and the primary villainous force of the film, and while he gives a committed and comedic performance as an over-the-top villain, the film is still a major downgrade from the previous entries. The film's lower budget was made directly apparent in the underwhelming practical effects, as well as actively going against the strengths of the previous films in one of the most painful sequels of all time.

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4 'Envy' (2004)

Directed by Barry Levinson

While Envy attempts to be a biting black comedy about the difficulties of human nature and one's inclination to be spiteful and envious in the face of others' success, its reliance on toilet humor and other cheap gags makes it a rather messy experience. The film follows everyman Tim Dingman (Ben Stiller), who grows increasingly annoyed with his friend Nick's insistence that his idea of a spray can that removes dog poop would be a massive success. Despite the outlandishness of the idea, Nick (Black) manages to not only create the spray but transform it into a massive global product, sparking envy and jealousy from Tim.

While there is inherent potential within the themes that make up Envy's conception, its core execution is simply too rooted in barbaric raunchy comedy tropes to make any meaningful difference or insightful comedy. It's a genuine shame that, instead of an actual effective satire, Envy is much more preoccupied with creating what mostly amounts to a feature-length poop joke. Both Black and Stiller have been in much greater comedies before, during, and after this era, so it's anyone's guess as to how this film managed to end up the way it did.

3 'Borderlands' (2024)

Directed by Eli Roth

Following the major box office success of films like Sonic the Hedgehog and Uncharted, video game movies have been a major blockbuster trend that has defined the 2020s, with one of the worst recent examples being Borderlands. The film takes place on a far-off planet where various thieves and bandits have collectively transformed it into a wasteland in search of a mysterious treasure known as the vault. While initially starting as a mission to save a young girl, bounty hunter Lilith (Cate Blanchett) finds herself as the latest hunter to find the hidden treasure of the planet Pandora.

While Borderlands ironically stays relatively true to the style of humor and tone of the videogame series, it simply does not work in the context of a theatrical film. The film suffers from painfully unfunny writing and some of the worst visual effects of recent memory, as well as an array of bad casting decisions across the board, with Black being one of them with his vocal performance as Claptrap. The character was already infamous for being an annoying nuisance in the games, yet Black's performance manages to further amplify the worst aspects of the character on-screen.

2 'Gulliver's Travels' (2010)

Directed by Rob Letterman

The original Gulliver's Travels novel is largely acclaimed as one of the most influential and notable works of satire of all time, having a powerful legacy with near-universal acclaim as a defining work of art of the 18th century. However, this modern family film adaptation of the classic tale eliminates any wit or strength of the original and turns it into a miserable, unfunny viewing experience. The film sees Black as Lemuel Gulliver, a travel writer who takes an assignment in the illusive Bermuda Triangle, where he ends up shipwrecked on an island inhabited entirely by tiny, inch-tall citizens.

Gone is the sense of adventure and biting social commentary on human nature from the original novel in service of product placement, low-effort toilet humor, and a completely phoned-in performance by Black. Black has proven himself to be an effective tool for biting and intelligent comedy a multitude of times during his career, yet Gulliver's Travels is only interested in using his weight and slapstick as a source of underwhelming comedy in the film.

1 'Year One' (2009)

Directed by Harold Ramis

A painful frat-bro approach to life in the prehistoric era, Year One squanders any and all potential comedy within its premise to be one of the worst comedies of the 2000s. The film follows the ventures of best friends Zed (Black) and Oh (Michael Cera), who are lazy hunter-gatherers who find themselves banished from their primitive village for not doing their fair share of work. As they wander the world in search of answers and a new home, they find themselves meeting an array of iconic figures from the ancient world, managing to mess up these classic stories in the process.

While the concept of a parody film that sees its unlucky heroes messing up various legendary biblical tales of old one after another sounds rife with comedic potential, the film's dated overabundance of raunchy humor ruins any potential within. Black and Cera are doing nothing here that they haven't done a million times in the past, with the writing seemingly going out of its way to hinder their abilities as comics as they trudge from one unfunny setpiece to the next.

NEXT: The 10 Best Jack Black Movies, Ranked