But while Nikki delivered the monologue with unwavering confidence, the star has now admitted that there was one specific joke that she was incredibly nervous to say on stage — and that she was waiting to get past the line before allowing herself to relax into the show.
During her appearance on SiriusXM’s The Howard Stern Show on Tuesday morning, Howard told Nikki that her comparing Sean Penn to a leather handbag was the moment he theorized that she must clear the jokes with the stars mentioned before the ceremony.
Reciting the one-liner in question, Nikki recalled: “I said: ‘You know, you’re such an original. Everyone in Hollywood is desperate to look younger. Meanwhile, Sean Penn is like ‘What if I slowly morphed into a sexy leather handbag?’”
“I said to my wife: ‘I think Nikki must clear it ahead of time with these people,” Howard said in response.
“That was one where I was like: ‘I think I need to,’” Nikki confessed. “I thought: ‘What is it gonna do in the room? If he makes a face, everyone in the room is not gonna laugh even if it is funny, and even if he does look exactly like a handbag.’”
But instead of going to Sean himself with her concerns, Nikki turned to some of their mutual acquaintances. She recalled: “I actually told Jimmy Kimmel that joke. I whispered it in his ear, he was like: ‘That guy, I don’t think he’s ever brushed his hair.’ He said: ‘That guy’s not vain. This isn’t gonna hurt his feelings.’”
“Because a lot of people were like: ‘Would you say that joke about a woman?’ and I’m like: ‘Well, no. I wouldn’t.’ And if someone said that about me, I would be devastated,” Nikki admitted. “But it’s different for men, and I was OK with doing that joke because I am attracted to him.”
“I watched that movie and my boyfriend was uncomfortable with how horny I was for him in that,” she added in reference to Sean’s latest film, One Battle After Another.
“He’s known as kind of a live wire, you don’t know, he might jump up on the stage and Will Smith you, you know what I mean? You just don’t know with this guy,” Howard then replied.
“Yes. I asked [David] Spade, because he kind of knows him, and he was like: ‘Yeah. That should be fine,’” Nikki explained. “Just everyone seemed to be in agreement that he was gonna be fine about it. That was the part of the monologue that I was just like: ‘Once I get past that, I’ll be OK.’”
Thankfully, David and Jimmy’s instincts were right, and Sean appeared to love Nikki’s joke, and was shown laughing along in the audience at it:
It’s worth mentioning that this wasn’t the only gag about Sean in Nikki’s monologue, with the host also sparking shockwaves when she said: “I feel like a lot of actors talk the talk, but Sean Penn will actually go to the places in the world that need help the most, and he will do cocaine there. And I feel like we don’t celebrate that enough.”
“Sean, I did get permission to do that joke from your two best friends,” she then quipped. “Charlie Sheen and El Chapo.”
Elsewhere in the Howard Stern interview, Nikki revealed the jokes that ended up on the cutting room floor — including this jab at Sydney Sweeney’s recent box office failures: “You know, people just aren’t going to the theaters to see things and if you don’t believe me, there was a movie this year where Sydney Sweeney played a lesbian who just bounced around in tiny shorts for two hours and it made $14.”

