
The movie Jack Black will regret for the rest of his life: “I wasn’t proud of it”
Although he can do a mean Jack Nicholson impression with his devious brow, Jack Black resides in a different corner of the Hollywood Hall of Fame. As a comedy actor, first and foremost, Black rarely takes on non-comedic roles. This doesn’t, however, mean he hasn’t experienced critical acclaim. On the contrary, Black has excelled in several roles, including that in School of Rock.
Released in 2003, Richard Linklater’s School of Rock was a highly engaging story written by Mike White with Black in mind for the role of impostor music teacher Dewey Finn. Black’s infectious personality shone throughout the music, as did his passion for rock ‘n’ roll, which he also exercises as one half of the rock duo Tenacious D and the related movie The Pick of Destiny.
Since 2003, Black has acted in a range of different movie roles, from the blockbusting Kung-Fu Panda movies to non-comedic highlights like King Kong and Bernie. Accordingly, he is revered for his versatility and ability to bring a range of emotions to the fore despite his deep associations with tongue-in-cheek roles.
During his pre-fame years in the 1990s, Black got to grips with acting in a run of supporting roles. These, too, contained a healthy variety, from the Jim Carrey comedy The Cable Guy to the classic Bruce Willis action thriller The Jackal. When Black finally broke through with his first starring role in 2000’s High Fidelity, he had very few regrets about his eclectic road to stardom. However, a lack of judgment was just around the corner.
In 2001, Black starred in Dennis Dugan’s poorly received comedy Saving Silverman. It’s fair to assume he might not have bothered with this role if he had his time again, but his real regrets lie in a project that hit the screens later in the year. Shallow Hal, directed by Peter Farrelly and Bobby Farrelly, attracted Black due to the directors’ previous success in the comedy genre with Dumb and Dumber and There’s Something About Mary. Still, the plot perhaps should have been a red flag for Black and his co-star, Gwyneth Paltrow.
In a past conversation with fellow comedian Rob Brydon, John Cleese bemoaned the false perception of comedy as a facile genre unworthy of attention at the Academy Awards. “I think there’s an extraordinary, completely incorrect idea that drama is somehow more important and more difficult than comedy,” he said. “Whereas, in my opinion, comedy is a great deal more difficult.”
The Monty Python legend continued to discuss Stanley Kubrick’s Dr Strangelove as a comedic masterpiece and lauded Peter Sellers’ acting in the 1963 movie. “There are some actors who can do funny and some very good actors who can’t, but I think all the very, very best comedians can act,” he opined. “It is an extraordinary prejudice that somehow seriousness or rather solemnity is more important than humour.”

I am inclined to agree with Cleese’s opinions regarding comedy movies. However, filmmakers don’t exactly give comedy a fighting chance when they saturate the playing field with moribund concepts and flaccid comedy. With this in mind, the idea of a man who sees an obese woman as skinny and, therefore, more attractive is unlikely to garner ‘Best Picture’ nominations.
Black reflected on his role in Shallow Hal in a 2006 interview, revealing a great deal of regret despite earning plenty of money from the role. “I had an opportunity to work with some dudes I thought were really funny, but it didn’t turn out as I’d hoped, I wasn’t proud of it, and I got paid a lot of money, so, in retrospect, it feels like a sell-out,” he said.
In Shallow Hal, Paltrow wears a fat suit in some of the scenes, which presents her as she looks to everyone but Black’s titular character. In the movie’s defence, the moral intention in teaching Hal about blind love was respectable, but the plot failed to induce laughter or engage the average viewer.
One of the central criticisms of Shallow Hal is its reliance on fatphobic jokes and stereotypes for humour. The film often uses Rosemary’s weight as a punchline, with visual gags about her size, such as breaking chairs or creating large ripples in a pool. It goes without saying, these moments undermine the film’s purported message of valuing inner beauty, as they lean heavily on the very biases and prejudices the movie ostensibly seeks to critique.
Speaking to The Guardian in 2006, Paltrow also voiced regrets about her role in Shallow Hal. After labelling the movie as one of her “shite” decisions, she discussed reservations about the fat suit. “The first day I tried the fat suit on, I was in the Tribeca Grand, and I walked through the lobby,” she said. “It was so sad. It was so disturbing. No one would make eye contact with me because I was obese. I felt humiliated. For some reason, the clothes they make for women that are overweight are horrible. I felt humiliated because people were really dismissive.”
Black, for what it’s worth, is trying. He brings a weird, soft sincerity to Hal that makes the character almost sympathetic. But the script keeps undermining him. Every attempt at genuine emotion gets undercut by some gag about chairs breaking or canoes tipping. Paltrow, meanwhile, seems trapped in a role designed by people who thought the ultimate fantasy was a thin woman pretending to be fat.
Rewatching it now, Shallow Hal feels like a relic. A museum piece from a time when “body positivity” was a punchline, and Hollywood genuinely thought slapping a moral on the end justified the means. Its heart might have been in the right place, but the execution reeks of male entitlement disguised as enlightenment. It’s not the worst thing the 2000s gave us, but it is right up there.
But, what movies has Black regretted not making?
Uniting with an idiosyncratic talent like Charlie Kaufman would have been the perfect showcase for Black’s untapped potential. But the proposed Frank and Francis project fell into the depths of development hell. Naturally, it was a musical satire set in Hollywood that Steve Carell and Nicolas Cage attached to co-star.
The two title characters were a filmmaker called Frank and a movie blogger called Francis, who fell into a heated feud with each other. Kaufman described the story as being about “cultural, societal, and individual anger” told through the lens of “people in the world wanting to be seen.”
Frank and Francis was officially announced in 2011, which is about as far as it got. It was a particular source of disappointment for Black, who admitted to Vulture that it was something he desperately wanted to be a part of.
“I wish that it would fucking happen, but I think it is a little too expensive for how ambitious it is,” he said. “It is a very surreal and dark look at Hollywood. I fucking love it. We are just about $10 million shy of the cost to make it, so if anyone out there can scrape together a cool ten-mil, this thing can happen.”