Inside the Abysmal Rom-Com That Is Probably Jack Nicholson's Last Role

Following 13 years and counting without a single acting job, Hollywood icon Jack Nicholson would rather read a book in the shade than make another movie – we would too if we swiped our last role from Bill Murray, only for the movie to lose $70 million dollars.

At the age of 86, with 80 film credits and three Academy Awards under his esteemed belt, Nicholson doesn’t have anything left to prove – which is convenient, since his last stretch of films during his sixties only proved that a hefty paycheck can temporarily postpone retirement for even the all-time greats. Since 2010, Nicholson has turned down opportunities to appear in big-budget blockbuster films like Ready Player One and reprise an iconic role in the Shining sequel Doctor Sleep, only emerging from his Beverly Hills mansion to hit the occasional Lakers game.

On a recent episode of WTF with Marc Maron, Lou Adler, a legendary film and music producer and a longtime friend of Nicholson’s, recalled a recent attempt to draw Nicholson out of retirement, saying, “A friend of mine wanted to put (Nicholson) in a movie, and he had a conversation with him. But Jack says, ‘I don’t want to do it.’ He goes, ‘You know what I did today? I sat under a tree and I read a book.’” With his acting days ostensibly behind him and his reading habit so voracious, it may be safe to say that we’ll never see another performance from the Mulholland Man – meaning that James L. Brooks’ massively disastrous 2010 rom-com How Do You Know will be his final film.

How Do You Know is a timeless tale of an archetypal love triangle – Paul Rudd is an embattled businessman who, after being framed for financial crimes by his lecherous father (played by Nicholson), falls inexplicably in love with professional softball player Reese Witherspoon, who is stuck in a live-in situationship with professional baseball player Owen Wilson. As Rudd’s legal troubles grow grim and his love for Witherspoon begins to blossom, he makes a bizarre bet with Nicholson – if he can convince Witherspoon to leave Wilson and be his girlfriend, Nicholson has to confess to his crimes, but, if he doesn’t get the girl, Rudd goes to prison. You know, totally normal rom-com stakes.

Despite appearing to be one of the many innocuous by-the-numbers rom-coms that Hollywood crapped out towards the end of genre’s boom in the 2000s, both How Do You Know and Nicholson’s appearance in the dud have some peculiarities that separate it from the pack of artistically bankrupt bombs – first, How Do You Know cost $120 million to make, breaking the absolute most important rule of soulless Hollywood rom-coms: make ‘em cheap. The beauty of the formula is the generous margins – the only significant operating cost should be the fee for the f-able A-listers who star as the central couple. 

However, Brooks, an industry icon and Simpsons veteran, had, for some reason, spent half a decade working on How Do You Know before he even started shooting, so by the time production actually began, he was so obsessive about making the film work that the shoots and re-shoots dragged on as the budget ballooned into nine figures. The salaries for the overloaded star power didn’t help either – between Brooks, Nicholson, Witherspoon, Rudd, and Wilson, the fees for the top talent alone cost $50 million, which was less than the gross total at the box office.

As for Nicholson’s role in the whole disaster, he wasn’t even supposed to appear in what would probably be his last film – Bill Murray was the original choice to play Paul Rudd’s dad, and the Saturday Night Live legend was already in rehearsals with the rest of the cast before some ominous on-set drama caused him to pull the plug. “Bill Murray started rehearsals with us,” Brooks once explained to USA Today, “Then personal things ensued. And very late in the game, he was forced to withdraw from our good ship. With Bill, it was… clinically personal." Nicholson was offered the last-minute role for a fee of $12 million, and the rest is box office bomb history.

So there you have it – Jack Nicholson’s (probably) final film was one of the biggest bombs in rom-com history, and he only ever got the part because Bill Murray is a bastard. No wonder he just wants a good novel and a seat in the shade.