Watch Madonna Hilariously Make Jimmy Fallon Squirm During All-Time Great Tonight Show Interview

Madonna has been pushing boundaries and subverting public opinion for almost five decades, whether you hate her or love her. As one of pop music’s greatest provocateurs, she's still pushing people’s buttons and making any mere man shutter with her antics, rebellious attitude and outspokenness. Though as many interviews as Madonna has done over the decades, I'm not sure anything will ever top her recent chat with Jimmy Fallon on The Tonight Show. She's appeared on the late-night show numerous times, yet this appearance seemed incredibly awkward for Fallon. As a matter of fact, he was actually squirming while trying to interview the music superstar.

Usually, when a guest comes on The Tonight Show Starring Jimmy Fallon, the titular host seems to have a rapport with the person. It allows the show to feel more like a chat between two friends rather than a fluffy softball interview. But Madonna being Madonna, it wasn’t going to be business as usual. While the late-night host did get some good stories from the pop singer, she made Fallon sweat a bit as she took over the conversation. You can watch The Tonight Show host shift in his chair as the singer takes control:

Even in the above clip, Jimmy Fallon admitted the pop icon makes him nervous every time she comes on the show. Madonna’s blunt commentary and cheeky innuendo seemed to throw Fallon off his game. (Honestly, talking about jelly squirters alone would make any man blush.) For every reply she gave, the late-night host seemed to get increasingly intimidated by her presence. But that was only part of the wildness that occurred on the late-night show.

Things seemed to get on track, as the host heaped praise on the songstress and her career. But after he mentioned the phrase “getting into good trouble,” singer sent Studio 6B in (thoroughly entertaining) chaos. Watch music’s biggest provocateur push the host's buttons even more:

Of course, she couldn’t resist the urge to lay across his desk. I mean who wouldn’t? It seems like a lovely place to take a catnap. But flashing her butt at the audience... it's just so… Madonna. The multi-faceted entertainer has never been one to just give basic answers and be prim and proper, it's just not her style. Of course, she's aware of her reputation and loves playing into it, which she clearly did here.

This is honestly far from the only awkward situation to happen on the show during the SNL alum's hosting tenure. There's just seems to be something about the show that brings out the most "interesting" sides of its guests.

I'm sure audiences would love to see more interviews like this one in the future. Jimmy Fallon getting flustered by Madonna’s mere presence makes the interview a must-watch for any fan of the singer or even just a casual viewer. And who knows, maybe this ordeal will be in the biopic she's working on

If you want to see who the host chats with next, make sure to check out The Tonight Show Starring Jimmy Fallon weeknights at 11:35 pm ET on NBC. Also, be sure to check out our fall 2021 TV schedule for info on the shows that are premiering or returning this season.

Adreon Patterson
News Writer

A boy from Greenwood, South Carolina. CinemaBlend Contributor. An animation enthusiast (anime, US and international films, television). Freelance writer, designer and artist. Lover of music (US and international).