Jack Nicholson, 87, hasn’t officially retired from acting, but he also doesn’t do it anymore. In 2013, Nicholson spoke with Vanity Fair about rumors of his retirement, and he merely wanted to say that he had retired from incessant flirting, not acting. He did admit, however, that he wasn’t passionately driven to put himself out in the world anymore. Nicholson’s good friend Lou Adler (the famed record producer) told Marc Maron in 2023 (via The Wrap) that Nicholson had been contacted several times about appearing in multiple film projects since 2010, but that Nicholson turned them all down. It seems that the actor would rather sit under a tree and read a book. Which is, of course, his right. With 80 film credits and multiple Academy Awards, not to mention worldwide fame, Nicholson has earned it. So, although he’s never announced his retirement, Nicholson is more or less retired.
And if Nicholson isn’t going to make any more movies in his life, then his final acting credit would be for James L. Brooks’ 2010 dramedy “How Do You Know.” Looking back, it was an inauspicious end to a prestigious career, as “How Do You Know” was lambasted by critics and bombed at the box office. Brooks’ film cost $120 million to make (presumably because of its high-caliber cast), but opened to a paltry $7.5 million weekend. It closed having made only $49.6 million, making it one of the biggest bombs of all time. When adjusted for inflation, “How Do You Know” lost more money than films like “Indiana Jones and the Dial of Destiny” and “Moonfall.”
In addition, “How Do You Know” has a mere 31% approval rating on Rotten Tomatoes. Anthony Lane, writing for the New Yorker, said that the film’s amusement factor is as absent as the question mark in the title, while Manohla Dargis described the film as “mirthless.” Roger Ebert likewise gave the film only two stars, saying that it felt more like a low-rent sitcom than a sensitive James L. Brooks film.
Few people saw Jack Nicolson in How Do You Know, and those that did didn’t like it
The plot of “How Do You Know” is a classic love triangle. Reese Witherspoon plays a star softball player named Lisa who, at age 30, is approaching retirement age. While she copes with the potential downturn in her career, she begins dating the sex-obsessed millionaire baseball star Matty (Owen Wilson), but seems to have a friendlier and more romantic regard with the gentle generic businessman George (Paul Rudd). George works for a firm run by his father, Charles (Nicholson), who hasn’t been running the company completely honestly. Charles is being investigated for fraud and could potentially serve a 25-year prison sentence. However, because George was working for the company, he would be punished by association. As such, Lisa has to choose between the rowdy, rich professional colleague and the gentle, romantic would-be felon. The film ends with Lisa finally realizing that she’s in love with … well, I daren’t give away the ending.
“How Do You Know” also featured small roles for notable actors like Tony Shalhoub, Teyonah Parris, Dean Norris, and Kathryn Hahn. Despite the star-studded cast and celebrity writer/director, though, most everyone stayed away.
Why did “How Do You Know” bomb? Perhaps it was merely bad. It also didn’t help that the film was marketed so poorly. The title is nondescript and the film’s posters only featured portraits of the actors, never alluding to the plot or the film’s actual events. It’s also possible that the public had grown sick of Brooks’ feature films. Although Brooks’ 1997 film “As Good as It Gets” was a major Oscar darling (it won Nicholson an Oscar and was nominated for Best Picture), he seemed to immediately run out of steam. Few liked his 2004 Adam Sandler vehicle “Spanglish,” and it took his six more years to make “How Do You Know.” By then, Brooks’ trademark sentimentality was no longer in vogue.
Jack Nicholson’s latter-day career was dominated by comedies
Prior to “How Do You Know” in 2007, Nicholson starred alongside Morgan Freeman in Rob Reiner’s old-man weepy “The Bucket List,” a film about two men with terminal lung cancer who decide to write a list of things they would like to do before they kick the bucket. Despite its sentimental premise, “The Bucket List” was an unexpected hit, making over $174 million on a $45 million budget. “The Bucket List” seemed like an odd turn for Nicholson, as he was more famous for playing darker, edgier roles. Even when he appeared in earlier Hollywood weepies like “Terms of Endearment,” the films seemed to be more dramatically earnest. “The Bucket List” had no edge whatsoever.
“The Bucket List” came on the heels of Nancy Meyer’s 2003 rom-com “Something’s Gotta Give,” another gentle romance wherein Nicholson falls in love with Diane Keaton. That film also had little edge, but was similarly a massive hit, grossing over $266 million. That same year, Nicholson faced off against Adam Sandler in Peter Segal’s rage comedy “Anger Management,” a clunky, bad film that, like many of Sandler’s projects, was inexplicably popular; it made over $195 million. Nicholson’s late-career niche seemed to be milking money from the least threatening Hollywood projects; he hadn’t given a characteristically dark performance since Sean Penn’s “The Pledge” in 2001.
The definitive performance of Nicholson’s post-2000 career is definitely the one he gave in Alexander Payne’s “About Schmidt.” His character was aggressively normal, even boring, which allowed Nicholson to play against type. It was sentimental, but honestly so, detailing the main character’s sticky emotional state after his wife, who he kind of hated, died unexpectedly. It’s one of his best performances.
“How Do You Know,” in contrast, feels like a favor to James L. Brooks.
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