Madonna Rides Jimmy Fallon And Otherwise Makes Him Super Uncomfortable In Her ‘Tonight Show’ Return

Back in October 2021, Madonna made a classic appearance on The Tonight Show, during which she seemingly made it her mission to make Jimmy Fallon as uncomfortable as she possibly could. Her (especially effective) tactics included flashing her butt and straddling his desk. Well, she popped back up on the show last night and it again seemed like her goal was to put Fallon in awkward spots.

Madonna opened the 17-minute interview by insisting she’s “not going to cause any problems.” A mere minute later, she declared, “This interview is going to be all about flirtation and seduction,” which got Fallon to bashfully cover his face with his hands. He quickly saw where she was going with that, though, tying it into Madonna’s recent Finally Enough Love: 50 Number Ones remix album.

A few minutes later, Madonna got to talking about the grills she was wearing in her mouth, saying, “I just like the way it looks, mouth jewelry. And I have really ugly teeth.” Fallon responded by asking, “You do,” although his inflection made it sound sort of like a statement and not a question. As Fallon added, “I don’t think you do,” Madonna said, “Don’t agree with me!” That got Fallon scrambling to clarify he was asking a question as the audience laughed and Madonna grabbed his hand to slap it.

Then, going back to an earlier part of the conversation about her hosting The Tonight Show, Madonna added, “See, when I host the show, I’m gonna make sure my guests feel really comfortable.” Fallon laughed and said, “I don’t think you will do that ever. You’ve never made me feel comfortable one time you’ve been here. Not one time, you’ve never made me feel comfortable.”

As Fallon was saying that, Madonna laughed as she thought Fallon pronounced the first syllable of “comfortable” like a certain four-letter words that starts with C.

Later in the interview, Madonna produced some flash cards, one for each letter of the alphabet, and she and Fallon played a simple game where they picked a card and said the first word that came to mind. Naturally, a lot of Madonna’s words were profane, which got the sort of reactions out of Fallon that she was looking for.

The game ended with the letter I, with Fallon saying “icon” and Madonna going with “idiot.” That got a laugh out of Fallon, who walked to the front of his desk and defeatedly collapsed on the floor face-down. Madonna saw her opportunity and took it, straddling his back, bouncing up and down, and pretending to whip him as he threw to commercial.

Before the interview, Madonna, Fallon, and The Roots performed a “classroom instruments” rendition of “Music.” Find that below and the interview above.