You probably don’t think of Paul Rudd and Jack Nicholson in the same sentence. One is the internet’s favorite ageless "nice guy" who fights Thanos with a van and some shrinking tech. The other is a three-time Oscar-winning titan of cinema who defines "cool" for an entire generation. They’re from different worlds. Different eras. Different vibes.
But back in 2010, they shared a screen. It was a movie called How Do You Know, a high-stakes romantic comedy that cost a staggering $120 million to make and basically vanished from the public consciousness within a month.
What most people don’t realize is that this movie represents a massive moment in Hollywood history. It was the final time Jack Nicholson ever appeared in a feature film. And the guy he chose to play his son? Paul Rudd.
The Most Expensive "Nice Guy" Movie Ever Made
Why does this matter? Honestly, it’s because How Do You Know is one of the weirdest artifacts of the 2010s. Director James L. Brooks—the guy who gave us As Good as It Gets and Terms of Endearment—spent years researching it. He interviewed pro athletes and corporate executives for hundreds of hours.
The budget ballooned. When you have Reese Witherspoon, Owen Wilson, Paul Rudd, and Jack Nicholson in one room, the payroll alone is enough to buy a small island. We're talking $50 million just for the talent. Nicholson took home about $12 million for his supporting role.
But the real gold wasn’t in the box office numbers (which were pretty grim, only grossing about $48 million). The gold was in the bizarre, wonderful chemistry between Rudd and Nicholson.
The Famous "First Meeting" Kiss
If you want to know what it’s like to work with Jack Nicholson, just ask Paul. He’s told this story on talk shows for years, and it never gets old.
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Rudd was understandably terrified. It’s Jack. The guy from The Shining. The Joker. He’s sitting in a room waiting for a rehearsal, heart pounding, probably trying to look like he belongs there. Nicholson walks in, doesn’t say a word, walks straight up to Rudd, grabs him by the shoulders, and kisses him right on the mouth.
He then looked at Rudd and said, "Right on the lips."
That set the tone.
The movie features a father-son relationship where the characters are constantly, almost aggressively, affectionate. Because director James L. Brooks is known for doing 70 or 80 takes of a single scene, Rudd and Nicholson ended up kissing on the lips dozens and dozens of times. Rudd later joked that of all the co-stars he’s had, Jack Nicholson is technically the person he has shared the most on-screen kisses with.
Why Paul Rudd and Jack Nicholson Actually Worked
On paper, they shouldn't fit. Nicholson is all sharp edges and chaotic energy. Rudd is the human equivalent of a golden retriever.
But in How Do You Know, that’s the point. Rudd plays George, a businessman who is being investigated by the feds for a financial crime he didn’t even commit. Nicholson plays his father, Charles, the actual criminal who is more than happy to let his son take the fall.
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It’s a dark dynamic for a rom-com.
Nicholson plays Charles as a mean-spirited, spittle-flying manipulator. It’s classic Jack, but refined. He uses that "toothy smile" to mask a total lack of empathy for his own kid. Rudd, meanwhile, plays George with this layered, existential crisis. He’s trying to be a "nice guy" while his life is literally imploding.
There is a scene in an elevator—no dialogue, just faces—where George realizes his world is collapsing and then sees Lisa (Reese Witherspoon) standing there. The way Rudd handles that transition from despair to hope is some of his best work. Having Nicholson as the looming, dark shadow in the background only makes Rudd’s "everyman" energy feel more grounded.
A Career-Ending Choice
A lot of film critics were baffled that Nicholson chose this as his final act. He didn't go out with a gritty drama or a massive blockbuster. He went out playing a jerk of a father in a movie that didn't even make back half its budget.
Since 2010, Nicholson has basically disappeared from Hollywood. He didn't give a big retirement speech. He didn't do a farewell tour. He just... stopped.
Reports from friends like Lou Adler suggest he’s just enjoying the quiet life. He likes "sitting under a tree and reading a book." He’s turned down dozens of scripts, including the Toni Erdmann remake he was once attached to. For Jack, How Do You Know was enough.
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The Legacy of the Duo
Even though the movie was labeled a "flop," it has found a weird second life on streaming. People are starting to appreciate the nuance James L. Brooks was going for. It’s a movie about "nice people" trying to survive "nasty people," and the Rudd-Nicholson dynamic is the beating heart of that theme.
If you’re a fan of either actor, here is why you should actually care about this pairing:
- Generational Hand-off: It feels like the passing of a torch. Nicholson represented the "New Hollywood" of the 70s—rebellious, intense, and unpredictable. Rudd represents the modern era—accessible, comedic, and relatable.
- The "Brooks" Factor: James L. Brooks is a legendary director who doesn't do "simple." Seeing him push Rudd into a more dramatic space alongside a veteran like Nicholson shows just how much range Rudd actually has.
- The Unfiltered Jack: This was the last time we saw the "Nicholson grin" on a cinema screen. Regardless of the plot, that alone makes it a piece of history.
What You Can Learn From This Hollywood Pairing
There’s something surprisingly human about the fact that even the biggest stars in the world don’t always "win" at the box office. How Do You Know reminds us that the experience of making something—the 70 takes, the weird kisses, the rehearsals with legends—often matters more than the Rotten Tomatoes score.
If you want to appreciate this duo, don't look for a masterpiece. Look for the small moments. Watch the way Rudd tries to stand his ground against a man who is twice his size in terms of "screen presence."
Actionable Insight for Film Fans:
If you want to see the "real" end of an era, skip the retrospectives and actually watch the final twenty minutes of How Do You Know. Pay attention to Charles’ (Nicholson) final interaction with George (Rudd). It’s not a grand apology. It’s a messy, complicated, and very real look at how some people never change, and how their kids have to learn to live with that.
The movie might be a "flop," but the performance of Paul Rudd and Jack Nicholson is a masterclass in how to act opposite someone with a completely different energy than your own. It’s a rare collision of two very different types of stardom.
To see more of Rudd's evolution after this role, his transition into the Marvel Cinematic Universe in 2015 provides a stark contrast to the grounded, anxious businessman he played opposite Nicholson. It’s as if working with a legend gave him the final bit of "leading man" confidence he needed to carry a franchise.
Now, if you're looking for a double feature, pair How Do You Know with As Good as It Gets. It’s the best way to see how James L. Brooks used Nicholson at the height of his power versus how he used him as a graceful, if slightly grumpy, exit from the stage.