All the Times Paul Rudd Tested Conan O'Brien's Patience With the Iconic Mac and Me

During promotion for the series finale of Friends, Paul kicked off what would become one of the longest-running bits in late-night TV. Under the guise of not realizing how intensely guarded the secrets of the finale were, he revealed that he had brought a clip from the episode. Instead of Friends, we got the now-infamous clip from the 1988 film.

Not realizing he'd be tricked again, Conan let Paul set up a clip from The 40-Year-Old Virgin. "Will I never learn with you?" Conan questioned his guest. Clearly, Conan learned nothing.

In honor of his Broadway run in Three Days of Rain, Paul discussed how a lot of people wouldn't get to see it so it was taped for the archives. After talking things over with Actors' Equity, he disclosed that he was able to bring a clip from the show. The sheer look of desperation on Conan's face at the end of the clip says everything.

Apparently, Judd Apatow wasn't pleased with Paul's prank during his promotion of The 40-Year-Old Virgin. When Paul visited Conan for 2007's Knocked Up, the director actually turned up for his Late Night appearance to ensure a clip from the movie was played. This led to Paul stating he could only do the Mac and Me bit for Role Models if he showed a clip of the movie. He then proceeded to show the Mac and Me clip for a second time, instead of something from Role Models.

This was the first time that Paul appeared on TBS's Conan, and he didn't waste the opportunity. "Every time, they don't tell me you're going to do it again," Conan explained after Paul shared the clip of the 1988 film. To not get in trouble, Paul included a clip from Our Idiot Brother, only for the clip to revert to Mac and Me. "You're wasting everybody's time," Conan added with an exasperated laugh.

While Judd may have prevented him from his Mac and Me bit for Knocked Up, that wasn't the case for This Is 40. Paul recalled how his kids used to think he just worked at a movie theater before getting to the Mac and Me clip. "How many times have you showed that clip on this show over the years?" Conan wondered. Paul, being as cheeky as ever, then responded, "We just shot that."

You'd think Conan would've finally learned after years of Paul pulling the prank that he would never willingly show an exclusive clip from one of his movies. "You've been showing that clip on my show for I think 15 years," O'Brien said after being Mac and Me-ed by Paul. "It's from a movie called Mac and Me. And you always convince me that you're not going to show it again. And you promise me that you're not going to show it again, and you show it again."

Although Paul didn't appear on this episode, he was the inspiration for Alana Nichols's prank. Instead of showing her highlight reel, she showed Paul's favorite clip from Mac and Me. "I've been watching your show for years. Paul Rudd is one of my favorite actors," the Paralympian shared. Conan replied: "Paul Rudd shows that clip every time he's on, no matter what movie he's promoting. And you decide to do that to me."

"You've been coming on the show for many, many, many years," Conan stated before Paul could show the clip. "And you do this one thing consistently which is you say we're gonna see a clip and then I throw to what I think is a clip and it turns out to be a clip from this terrible E.T. rip-off called Mac and Me." Much like with Role Models, Paul explained that the studio wouldn't let him do the bit and he had to show a clip from the movie. This time, Paul as Ant-Man made an appearance in the 1988 film.

On Netflix's Living With Yourself, Paul plays twins. To jazz up the prank, the clip ended with twin aliens instead of a single Mac. "Do you want to show a real clip? You son of a b*tch," Conan said with a shake of his head. As Conan continued laughing, Paul deadpanned, "That was a real clip."

Sadly, the Mac and Me bit had to come to an end since Conan is ending its run on TBS. Thinking he'd be able to avoid another Paul Rudd incident, Conan interviewed Bill Hader about the worst Saturday Night Live sketch he'd ever been in. Of course, it included Paul, who appeared in a tuxedo to commemorate the bit. "It's been like 25 years of you coming on the show. You'd always say, 'I've got a clip,' but every time, for years, I would be convinced that I would see the real clip because you're such a genuinely nice person," Conan explained. "And you would say, 'No, this movie's really important to me. I put my own money into this, and I really care about this,' and then you pull that sh*t every time."