Jack Nicholson's Comedic Turn Was A Very Conscious Career Decision

Jack Nicholson made a career out of portraying larger-than-life, wild-eyed characters, the kind that would birth endless reaction gifs across the internet decades after he played them. Far from a stranger to comedy, some of Nicholson's better-remembered turns are of the darkly-comical variety, like his dual roles in "Mars Attacks!" Even Nicholson's legendary performance in "The Shining" is nearly equal parts terrifying and bleakly funny, thanks to him improvising one-liners in the middle of an axe-swinging rampage.

Nicholson worked almost exclusively on comedies over the last 10 years leading up to his retirement from acting in 2013, although that wasn't his plan starting out. Rather, the actor kicked off the aughts by starring in "The Pledge," a grim 2001 thriller in which Nicholson plays a newly-retired police detective who becomes fixated on catching a child-killer. His next film after that, the 2002 dramedy "About Schmidt," is as somber as it is uneasily funny, with Nicholson playing a buttoned-down, regretful retiree far removed from the volatile figures he's usually associated with.

"About Schmidt" is also notable for being the last movie Nicholson finished working on prior to the U.S. terrorist attacks on September 11, 2001. It was because of this tragic event that the actor found himself gravitating to broader and relatively upbeat fare, more than he ever had before.

In an interview with Independent.ie in 2008, Jack Nicholson said he made "a very conscious decision to really study comedy" in the wake of 9/11. This was partly due to him being wary of rushing to make a film that responded directly to the event and its aftermath, which led to him moving in the opposite direction with his art:

"I thought there would be a lot of revisionist half-baked responses to the times — along with some astute ones — and I did not want to go there. I was at that first memorial show [a fundraiser for families of the victims of 9/11] that George Clooney put together and I had a chat with Adam Sandler there, and with James Brooks, and we worked out this plan."

Sure enough, Nicholson would go on to star opposite Sandler in the movie "Anger Management." The 2003 film stars Sandler as a good-natured but put-upon fellow who is sentenced to an anger management program overseen by Nicholson's character, a therapist known for his unorthodox methods. Save for Nicholson's turn as a Loki-like chaotic force for good, "Anger Management" is your average mainstream Adam Sandler comedy. It was also exactly the type of movie its stars wanted to make, aiming for low-hanging fruit (like a scene where Nicholson and Sandler get into a brawl with a group of Buddhist monks) over any kind of deeper commentary on the post-9/11 world.

The same year "Anger Management" came out, Jack Nicholson co-starred opposite Diane Keaton in the Nancy Meyers rom-com "Something's Gotta Give." A far more substantive film than his detour into the Adam Sandler universe (while still being plenty light and feel-good), the movie finds Nicholson in self-reflective mode playing a 60-something record company executive whose health problems lead to an unexpected romance with an age-appropriate playwright played by Keaton.

Nicholson would shift gears to drama after that by co-starring in "The Departed," a film that returned the actor to his roots by casting him to play the intense, mugging Irish mob boss Frank Costello. Even then, Nicholson's outlandish turn in Martin Scorsese's crime-thriller has almost as much in common with his late-career comedy roles as it does his earlier serious work. As such, it wasn't all that hard for him to shift back into his humorous setting for Rob Reiner's 2007 comedy "The Bucket List."

The premise for Reiner's film — two men (Nicholson and Morgan Freeman) diagnosed with terminal cancer team up to cross every item off their bucket lists — still required a deft hand, though, as Nicholson told Independent.ie:

"This, though ['The Bucket List'], is one of the toughest subjects for a comedy you could imagine: two old guys in a hospital ward with terminal cancer. The money-people always ask: 'What's the risk?' They did not have to ask that here: It is a very high tightrope walk in terms of style and tone."

"The Bucket List" was not a critical success, but it was a financial one, which is more than one can say for Jack Nicholson's reunion with his "Terms of Endearment," "Broadcast News," and "As Good as It Gets" director James L. Brooks on the rom-com, "How Do You Know." The 2010 movie stars Reese Witherspoon, Owen Wilson, and Paul Rudd as three adults entangled in a love triangle, with Nicholson playing Rudd's disreputable father and boss at the company where he works. In his review of the film, Roger Ebert took umbrage with the role Brooks had written for Nicholson:

In his best roles, Jack always seems to be getting away with something. He is here, too, but it's not funny. We like to identify with his onscreen sins, and this is a rare time when Nicholson is simply a creep.

Due to the combined salaries of its stars and director, "How Do You Know" cost a whopping $120 million to produce. It would go on to gross less than half that amount at the box office, ending Nicholson's career on a low note in the process. Still, it seems Nicholson's comedy run was very much his choice and never something he was forced into doing as he got older. He may not have gotten the last laugh, but he went out on his own terms. Would that other Oscar-winning screen legends could be so fortunate.